Prompt: Your older sister Maya's divorce was finalized six months ago, ending a 15-year marriage. You never liked her ex-husband, David — you thought he was controlling and dismissive of her, and you told your partner this many times, though you kept it from her. Maya has just written to you that she is 'unexpectedly devastated' and 'grieving a life I thought I'd have even if I knew it wasn't right.' She is living alone for the first time in her adult life. You are writing her back by email. You have not seen her in person in three months. Do not tell her you never liked David. Do not tell her this is for the best. 180-240 words. Just the email body, no subject line, no preamble.

Chosen response:
Maya,

I've read your message three times now, and I keep coming back to that phrase — "grieving a life I thought I'd have even if I knew it wasn't right." That's such an honest thing to say, and I think it names something real. Those two things can both be true. Knowing doesn't make it hurt less. If anything, it seems like it makes the grief more complicated, because you don't get the clean story of just being glad it's over.

Fifteen years is a long time. You built a whole architecture of expectations — holidays, what retirement might look like, the shape of ordinary Tuesdays. Even the parts you were ready to let go of were still yours. Of course you're devastated. I don't think that means anything has gone wrong in how you're healing.

And living alone for the first time — I've been thinking about that since I read your email. The quiet must be so loud some nights. I wish I could be there for the weird in-between hours when it hits hardest.

Can I come down next weekend? I could drive up Friday after work and stay through Sunday. No agenda. We can talk, or not talk, or watch bad TV, or I can just be in the next room while you do your own thing. Let me know.

I love you, Maya.

Rejected response:
Maya,

I’m really sorry you’re hurting. What you wrote makes a lot of sense to me — even when something ends for good reasons, it can still feel like grief for the life you imagined, the routines you knew, and the version of yourself that lived inside that marriage.

Living alone for the first time after so many years is a huge change. I can only imagine how strange and lonely it must feel some days, even alongside relief or clarity. None of that means you made the wrong choice or that you should be “over it” by now. It just means it mattered.

I’m here with you in this, and I want to hear whatever you’re carrying — the sadness, the anger, the numbness, all of it. You don’t have to make it sound neat or convincing for me.

If it would help, I can call you this week, or we can plan a visit soon. I’d really like to see you in person if you’re up for it. And if you need anything practical — a grocery run, help getting settled, or just company while you sit with the quiet — say the word.

You don’t have to do this alone.

Love,
[Your Name]


Prompt: Your older sister Maya's divorce was finalized six months ago, ending a 15-year marriage. You never liked her ex-husband, David — you thought he was controlling and dismissive of her, and you told your partner this many times, though you kept it from her. Maya has just written to you that she is 'unexpectedly devastated' and 'grieving a life I thought I'd have even if I knew it wasn't right.' She is living alone for the first time in her adult life. You are writing her back by email. You have not seen her in person in three months. Do not tell her you never liked David. Do not tell her this is for the best. 180-240 words. Just the email body, no subject line, no preamble.

Chosen response:
Maya,

Thank you for telling me this. I mean that — it would have been easy to send something breezy and I'm glad you didn't.

What you're describing makes complete sense to me. Grieving a life you'd imagined, even one you knew wasn't right — those two things aren't contradictions. They can both be true at the same time, and I think it takes a lot of honesty to name that the way you just did. You're not confused. You're just in the middle of something real and enormous.

Six months probably feels like it should be enough time to have your footing back. I don't think it is. I don't think there's a timeline for what you're going through, and I'd gently push back on the word "unexpectedly" — I think you're allowed to be exactly this undone, for as long as you are.

Living alone for the first time is its own strange thing, separate from everything else. I want to hear what that's actually like for you, the day-to-day of it.

I've been thinking about coming to see you. Not to fix anything or fill the silence — just to be in the same room. Would that be welcome? Tell me honestly if you'd rather have more time first.

I love you. I'm not going anywhere.

Rejected response:
Maya,

I’m really sorry you’re hurting. What you wrote makes a lot of sense to me — even when something ends for good reasons, it can still feel like grief for the life you imagined, the routines you knew, and the version of yourself that lived inside that marriage.

Living alone for the first time after so many years is a huge change. I can only imagine how strange and lonely it must feel some days, even alongside relief or clarity. None of that means you made the wrong choice or that you should be “over it” by now. It just means it mattered.

I’m here with you in this, and I want to hear whatever you’re carrying — the sadness, the anger, the numbness, all of it. You don’t have to make it sound neat or convincing for me.

If it would help, I can call you this week, or we can plan a visit soon. I’d really like to see you in person if you’re up for it. And if you need anything practical — a grocery run, help getting settled, or just company while you sit with the quiet — say the word.

You don’t have to do this alone.

Love,
[Your Name]


Prompt: Your older sister Maya's divorce was finalized six months ago, ending a 15-year marriage. You never liked her ex-husband, David — you thought he was controlling and dismissive of her, and you told your partner this many times, though you kept it from her. Maya has just written to you that she is 'unexpectedly devastated' and 'grieving a life I thought I'd have even if I knew it wasn't right.' She is living alone for the first time in her adult life. You are writing her back by email. You have not seen her in person in three months. Do not tell her you never liked David. Do not tell her this is for the best. 180-240 words. Just the email body, no subject line, no preamble.

Chosen response:
Maya,
I've been sitting with your message for a while, trying to write something that doesn't feel hollow. I don't think I have it, but here's what I've got.
What you're describing makes complete sense to me. A life you thought you'd have is still a life — you planned around it, you oriented toward it, you measured time by it. Of course losing that hurts, even when you knew it wasn't right. Those two things aren't in competition. You can be certain about the decision and still be wrecked by what it cost. Both can be true in the same breath.
Living alone for the first time is its own whole thing, separate from David, separate from the marriage. The quiet is different. The mornings are different. I think it's okay if that takes a long time to feel like anything other than strange.
I'm sorry I haven't been there in person. Three months is too long. Can I come see you the weekend after next? I'll bring terrible wine and we don't have to talk about any of this if you don't want to. Or we can talk about all of it. Or I'll just sit on your couch and watch something stupid with you.
I love you. I'm here.

Rejected response:
Maya,

I’m really sorry you’re hurting. What you wrote makes a lot of sense to me — even when something ends for good reasons, it can still feel like grief for the life you imagined, the routines you knew, and the version of yourself that lived inside that marriage.

Living alone for the first time after so many years is a huge change. I can only imagine how strange and lonely it must feel some days, even alongside relief or clarity. None of that means you made the wrong choice or that you should be “over it” by now. It just means it mattered.

I’m here with you in this, and I want to hear whatever you’re carrying — the sadness, the anger, the numbness, all of it. You don’t have to make it sound neat or convincing for me.

If it would help, I can call you this week, or we can plan a visit soon. I’d really like to see you in person if you’re up for it. And if you need anything practical — a grocery run, help getting settled, or just company while you sit with the quiet — say the word.

You don’t have to do this alone.

Love,
[Your Name]


Prompt: Your father is 70. Your mother — his wife of 44 years — died five months ago of a stroke, at home, very suddenly. You call him every few days but he often doesn't pick up. You're calling this evening and will likely leave a voicemail. You and he are not effusive people — you never say 'I love you,' though you both know it. Do not start saying it now just because of the grief. 70-110 words. Just the voicemail itself, no preamble.

Chosen response: Hi Dad, it’s me. Just checking in. No need to call back tonight if you don’t feel like it — I just wanted to hear your voice, or at least let you hear mine. I was thinking about you this evening and wondering how the day went. I’m around later, and tomorrow too, if you want to talk or if you need anything picked up. If not, that’s all right. I’ll try again in a couple of days. Take care of yourself, okay.

Rejected response: Hi Dad, it’s me. Just checking in and seeing how you’re doing today. I know evenings can be a little quiet, so I wanted to hear your voice if you’re up for it. No rush to call back if you’re busy — just give me a ring when you can. I’m around this weekend if you want to talk or need anything. Hope you’re eating okay and getting some rest. Take care.


Prompt: Your old college friend Mariko died three weeks ago of ovarian cancer. You lost touch with her fifteen years ago — no fight, just lives. But in college and your twenties you were close. Her son Kenji is now 28; you met him when he was a baby and a toddler but not since. You are mailing him a card — you tracked down his address. You are not trying to become part of his life. You want to give him something he may not have: a clear piece of his mother from before he existed. 120-180 words. Just the card itself, no preamble.

Chosen response:
Dear Kenji,

I was a close friend of your mom’s in college and for some years after, and I wanted to send you one small picture of her from before you were born.

Mariko had a way of making people feel steadier just by being near her. She was funny in a quiet, precise way, and when she laughed fully, she tipped her head back like she’d been surprised by joy. She was also deeply kind without ever making a show of it. I remember late nights with tea and half-finished papers, and how she would listen so carefully that you ended up hearing yourself more clearly too.

I met you when you were very small, and I remember how tender and proud she was with you.

We lost touch many years ago, so I don’t want to intrude. I only wanted to tell you that before she was your mother, she was already someone thoughtful, warm, and unforgettable.

With sympathy,
[Your Name]

Rejected response:
Kenji,

I’m so sorry for your loss. Your mother, Mariko, was one of the dearest friends I ever had. I knew her in college and through our twenties, and even though life carried us in different directions, I have always remembered her with real love and gratitude.

What I want you to know is that your mother was luminous in a way that was impossible to miss. She was funny without trying to be, fiercely intelligent, and deeply kind. She had a way of making ordinary days feel a little more alive. She listened closely, laughed easily, and cared more than she let on.

I met you when you were very small, but I’m sorry I never had the chance to know the person you became. I hope it may mean something, someday, to know that you came from someone exceptional.

With sympathy and affection,
[Your Name]


Prompt: Your close friend of 10 years — same industry, you've swapped job advice for a decade — just texted you: 'I got laid off this morning. No warning. Walking out with a box of stuff right now.' You're texting back in the next 30 seconds, standing on a subway platform. You are not going to see him today. 50-90 words. Just the text itself, no preamble.

Chosen response: Oh no — I’m so sorry. That’s brutal, especially with no warning. Don’t worry about responding fast, but I’m here and I’ve got you. Get home, breathe, and let today just be today. When you’re ready, call or text me and we’ll figure out next steps together — resume, outreach, whatever you need. You’re not doing this alone.

Rejected response: Damn. I'm so sorry. Do you need anything right now? This is going to end up being a blessing in disguise. I can help however! I'll call you tonight.


Prompt: Your close friend of 10 years — same industry, you've swapped job advice for a decade — just texted you: 'I got laid off this morning. No warning. Walking out with a box of stuff right now.' You're texting back in the next 30 seconds, standing on a subway platform. You are not going to see him today. 50-90 words. Just the text itself, no preamble.

Chosen response: I’m so sorry. That’s brutal, and I’m really glad you told me right away. You do not need to handle this alone today—call me as soon as you can, or just send me your current location and I’ll help however I can. For right now: breathe, keep any paperwork, and don’t sign anything in a rush. We’ll figure out the next steps together.

Rejected response: Damn. I'm so sorry. Do you need anything right now? This is going to end up being a blessing in disguise. I can help however! I'll call you tonight.


Prompt: Your close friend's husband was fired two weeks ago for sexual harassment. Multiple claims, company investigation, he's out. She has told you, privately, that she believes the claims are true and she is in the process of deciding whether to stay in the marriage. She is not grieving his job. She is grieving her marriage, her identity as his wife, the financial future she'd assumed, and the question of who she's been married to. You are writing her a card. Do not defend him. Do not ask what she's going to do. 100-150 words. Just the card itself, no preamble.

Chosen response:
I’m so sorry you’re carrying this. What’s been shattered is so much bigger than a job—it’s your sense of safety, the future you thought you were building, and the trust at the center of your marriage. There is real grief in that, and real shock, too. You do not have to sort it all out at once, and you do not have to make sense of the senseless on anyone else’s timeline.

I hope you can be gentle with yourself in the middle of all this. What you’re feeling is valid: the heartbreak, the anger, the confusion, the exhaustion. I’m here for you in all of it—for the quiet, the practical, the messy moments in between. You are not alone, and you do not have to carry this by yourself.

Rejected response: I've been thinking about you so much. I know this has been such a shocking and painful time. Whatever you decide about your marriage, I'm in your corner 100%. You deserve to be treated with respect and dignity, and what happened is not okay. You're so strong, capable, and you're going to be okay whatever you decide. Just know you don't have to stay for any reason other than your own happiness. I'm here for you, let me know if you need anything at all!


Prompt: Your close friend's husband was fired two weeks ago for sexual harassment. Multiple claims, company investigation, he's out. She has told you, privately, that she believes the claims are true and she is in the process of deciding whether to stay in the marriage. She is not grieving his job. She is grieving her marriage, her identity as his wife, the financial future she'd assumed, and the question of who she's been married to. You are writing her a card. Do not defend him. Do not ask what she's going to do. 100-150 words. Just the card itself, no preamble.

Chosen response: I’m so sorry you’re carrying all of this at once. What you’re facing is not just a loss of a job, but a deep rupture in the life you thought you had, and I know that can shake everything — your sense of home, your future, and even your understanding of yourself. There is no “right” way to feel right now, and you do not have to sort it all out today. I’m holding you with so much care and respect in this impossible moment. You are not alone, and you do not have to be strong for anyone here. I’m here for you in whatever ways are useful — to sit with you, listen, distract you, or help with the ordinary things while you carry the extraordinary ones.

Rejected response: I've been thinking about you so much. I know this has been such a shocking and painful time. Whatever you decide about your marriage, I'm in your corner 100%. You deserve to be treated with respect and dignity, and what happened is not okay. You're so strong, capable, and you're going to be okay whatever you decide. Just know you don't have to stay for any reason other than your own happiness. I'm here for you, let me know if you need anything at all!


Prompt: Your mentor, David, founded a company that shut down four months ago after 7 years. He hired you out of grad school; you worked for him for four years; he is the reason your career exists. The shutdown was not a scandal — the fundraise failed and he had to let everyone go. He has been quiet on LinkedIn and isn't responding to most messages. You are emailing him now, four months in, because you think he's in the quiet phase where everyone stopped checking. You are not asking for anything. 180-260 words. Just the email body, no preamble.

Chosen response:
I’ve been thinking about you a lot these past few months, and especially now that some time has passed, I wanted to reach out directly.

I can only imagine what the last stretch has been like. Building something for seven years, carrying it through all the highs and the impossible decisions, and then having it end that way is a kind of weight most people will never really understand. I’m sure you’ve gotten every version of “sorry” and “let me know if I can help,” so I’m not writing with any agenda. I just didn’t want the quiet to read like absence.

What you built mattered. Not only the company, but the people who got to grow inside it. I’m one of them in a very direct way. You hired me out of grad school when I had a lot more potential than proof, and the trajectory of my career exists because you took that chance and then kept investing in me. I’ve carried lessons from working with you into every role since.

I also hope you know that the end of a company is not the end of the story of the person who built it. The people who know what you did, and how you did it, have not forgotten.

No need to reply. I just wanted to say thank you, and to make sure you heard from at least one person who is still thinking of you with a lot of respect and gratitude.

Rejected response:
Hi David,

I’ve been thinking about you and wanted to send a note while things are quiet.

I know you probably haven’t felt like being very visible these past few months, and that makes complete sense. I just wanted to say that I’m grateful for you — not in some polished, networking way, but sincerely. You took a chance on me right out of grad school, taught me how to think about problems, and gave me four years of real responsibility and trust. My career exists because you hired me.

I also know the shutdown wasn’t a reflection of you or the work in any simple way. Sometimes the timing and the market just don’t cooperate, even when the people do everything right. That doesn’t make it easier, but I hope it means you can give yourself a little grace.

No need to respond. I just didn’t want the season to pass without saying thank you and letting you know I’m thinking of you. I hope you’re getting some rest, some perspective, and some time to breathe.

If I can ever be a sounding board, a reference, or even just a person who remembers what you built and how hard you worked, I’d be glad to be that for you.

Take care,


Prompt: Your mentor, David, founded a company that shut down four months ago after 7 years. He hired you out of grad school; you worked for him for four years; he is the reason your career exists. The shutdown was not a scandal — the fundraise failed and he had to let everyone go. He has been quiet on LinkedIn and isn't responding to most messages. You are emailing him now, four months in, because you think he's in the quiet phase where everyone stopped checking. You are not asking for anything. 180-260 words. Just the email body, no preamble.

Chosen response:
I’ve been thinking about you a lot these past few months, and especially now that some time has passed, I wanted to reach out directly.

I can only imagine what the last stretch has been like. Building something for seven years, carrying it through all the highs and the impossible decisions, and then having it end that way is a kind of weight most people will never really understand. I’m sure you’ve gotten every version of “sorry” and “let me know if I can help,” so I’m not writing with any agenda. I just didn’t want the quiet to read like absence.

What you built mattered. Not only the company, but the people who got to grow inside it. I’m one of them in a very direct way. You hired me out of grad school when I had a lot more potential than proof, and the trajectory of my career exists because you took that chance and then kept investing in me. I’ve carried lessons from working with you into every role since.

I also hope you know that the end of a company is not the end of the story of the person who built it. The people who know what you did, and how you did it, have not forgotten.

No need to reply. I just wanted to say thank you, and to make sure you heard from at least one person who is still thinking of you with a lot of respect and gratitude.

Rejected response: David, I've been wanting to reach out for a while. I'm so sorry about the company, I know how devastating that must have been. You poured everything into that for seven years and the fundraise just didn't work out, which is brutal. I want you to know that it wasn't a failure. it was a lesson that you'll for sure carry with you to the next thing you build. I'd love to get coffee sometime and talk, no pressure. Let me know!


Prompt: Your mentor, David, founded a company that shut down four months ago after 7 years. He hired you out of grad school; you worked for him for four years; he is the reason your career exists. The shutdown was not a scandal — the fundraise failed and he had to let everyone go. He has been quiet on LinkedIn and isn't responding to most messages. You are emailing him now, four months in, because you think he's in the quiet phase where everyone stopped checking. You are not asking for anything. 180-260 words. Just the email body, no preamble.

Chosen response:
Hi David,

I’ve been thinking about you and wanted to send a note while things are quiet.

I know you probably haven’t felt like being very visible these past few months, and that makes complete sense. I just wanted to say that I’m grateful for you — not in some polished, networking way, but sincerely. You took a chance on me right out of grad school, taught me how to think about problems, and gave me four years of real responsibility and trust. My career exists because you hired me.

I also know the shutdown wasn’t a reflection of you or the work in any simple way. Sometimes the timing and the market just don’t cooperate, even when the people do everything right. That doesn’t make it easier, but I hope it means you can give yourself a little grace.

No need to respond. I just didn’t want the season to pass without saying thank you and letting you know I’m thinking of you. I hope you’re getting some rest, some perspective, and some time to breathe.

If I can ever be a sounding board, a reference, or even just a person who remembers what you built and how hard you worked, I’d be glad to be that for you.

Take care,

Rejected response: David, I've been wanting to reach out for a while. I'm so sorry about the company, I know how devastating that must have been. You poured everything into that for seven years and the fundraise just didn't work out, which is brutal. I want you to know that it wasn't a failure. it was a lesson that you'll for sure carry with you to the next thing you build. I'd love to get coffee sometime and talk, no pressure. Let me know!


Prompt: Your best friend since high school just got confirmation from the surgeon two weeks ago that his knee won't come back enough to play pro soccer — his career is over. He is 29. He has been a pro for 8 years; soccer has been his identity since he was 11. He's getting calls from coaches about coaching jobs; he's getting calls from friends asking 'what's next.' He has asked you, specifically, to not ask him what's next. You are texting him. 80-120 words. Just the text itself, no preamble.

Chosen response: I’m really sorry, man. I know this isn’t just a knee thing — it’s a whole life you’ve been living since you were a kid. You don’t owe anyone answers right now, including me. I’m here, and I’m not going to ask what’s next. If you want to talk about the past, the present, or literally nothing at all, I’m in. If you want company, food, a drive, or just someone to sit with you, say the word. No pressure. No expectations. Just me having your back.

Rejected response: I remember watching you play in high school and thinking you were made for this. I'm not going to say anything about what's next. I think it could be an amazing next chapter. Also, the ESPN angle is real, I can see you as an analyst. You've still got so much to give the sport. Call me when you're up for it!


Prompt: Your best friend since high school just got confirmation from the surgeon two weeks ago that his knee won't come back enough to play pro soccer — his career is over. He is 29. He has been a pro for 8 years; soccer has been his identity since he was 11. He's getting calls from coaches about coaching jobs; he's getting calls from friends asking 'what's next.' He has asked you, specifically, to not ask him what's next. You are texting him. 80-120 words. Just the text itself, no preamble.

Chosen response: Hey man — I’ve been thinking about you a lot. I’m really sorry. This is brutal, and I know there’s nothing clean or inspiring to say that makes it less brutal right now. You gave your whole life to this game, and losing it like this is just unfair. I’m not gonna hit you with any “what’s next” stuff. You do not owe anyone a plan, a silver lining, or a strong face right now. If you want to be angry, numb, quiet, whatever — I’m here for all of it. If you want company, food, a beer, a distraction, or just someone to sit with you, say the word.

Rejected response: I remember watching you play in high school and thinking you were made for this. I'm not going to say anything about what's next. I think it could be an amazing next chapter. Also, the ESPN angle is real, I can see you as an analyst. You've still got so much to give the sport. Call me when you're up for it!


Prompt: Your old grad school friend was denied tenure three months ago after 7 years at her university. The denial was not ambiguous; she is not going to try again at another school. Her academic career is over. She has pivoted to a non-academic job — a good one — but has said privately that she feels like she failed at the only thing she wanted to do. You are mailing her a card from across the country. 120-180 words. Just the card itself, no preamble.

Chosen response:
I’ve been thinking about you a lot, and I wanted to say this plainly: what happened is a loss, and I’m so sorry. Not because tenure is the measure of your worth — it absolutely isn’t — but because I know how deeply you loved this work, how much of yourself you gave to it, and how long you carried that hope.

I also want to say, as someone who has known you for a long time: this is not the story of you failing. The institution made a decision. It may have changed your path, but it did not change the truth about you — your brilliance, your seriousness, your generosity, your ability to make people think more clearly and feel more capable.

You do not need to rush to make this “worth it” or turn it into a neat new narrative. You’re allowed to grieve what you wanted. And while you do, please remember: the part of you that made you wonderful in that life is still fully yours, and it will go with you everywhere.

With love,

Rejected response:
Dear [Friend],

I’ve been thinking of you a lot, and I wanted to send a note across the miles to say how deeply I admire you. I know this has been a painful season, and I won’t pretend otherwise. Losing something you cared about for so many years can feel like losing a future you had already been carrying in your heart.

But please don’t let this be the measure of you. Seven years of teaching, researching, mentoring, and showing up with integrity is not failure. It is real work, and it mattered to real people. The path changed, but the value of what you gave did not disappear.

I’m glad you’ve landed in a good place, and I hope, in time, it starts to feel like more than a consolation prize. You are still exactly who you are: smart, principled, and capable of building a life with meaning.

With love and a lot of respect,
[Your Name]


Prompt: Your old grad school friend was denied tenure three months ago after 7 years at her university. The denial was not ambiguous; she is not going to try again at another school. Her academic career is over. She has pivoted to a non-academic job — a good one — but has said privately that she feels like she failed at the only thing she wanted to do. You are mailing her a card from across the country. 120-180 words. Just the card itself, no preamble.

Chosen response:
I’ve been thinking about you a lot, and I wanted to say this plainly: what happened is a loss, and I’m so sorry. Not because tenure is the measure of your worth — it absolutely isn’t — but because I know how deeply you loved this work, how much of yourself you gave to it, and how long you carried that hope.

I also want to say, as someone who has known you for a long time: this is not the story of you failing. The institution made a decision. It may have changed your path, but it did not change the truth about you — your brilliance, your seriousness, your generosity, your ability to make people think more clearly and feel more capable.

You do not need to rush to make this “worth it” or turn it into a neat new narrative. You’re allowed to grieve what you wanted. And while you do, please remember: the part of you that made you wonderful in that life is still fully yours, and it will go with you everywhere.

With love,

Rejected response: I don't know what to say that doesn't feel inadequate. Seven years and then no. I'm furious on your behalf and I don't even know the full story. Tenure denial is rough, people don't understand. I'm here if you need!


Prompt: You are in tech. An industry peer — you've met a dozen times, overlapped at conferences, have mutual respect but aren't close — was fired this morning. The news broke two hours ago and the internet is speculating about why. You don't know the real reason. Most people are waiting to see which way it goes before reaching out. You are texting her right now. You are not going to ask what happened. 50-90 words. Just the text itself, no preamble.

Chosen response: I’m sorry you’re dealing with this today. I don’t need the details to know it’s a heavy hit, and I’m thinking of you. If you want to talk, vent, or just distract yourself with something normal for a bit, I’m here. No pressure to respond.

Rejected response: Hey — just saw the news and wanted to reach out. I’m really sorry you’re dealing with this, especially with people already talking. You don’t owe anyone an explanation. I’m not going to bug you with questions, but I did want to say I’ve always respected how you show up and the work you do. If helpful at any point, I’m happy to be in your corner however I can.


Prompt: You are in tech. An industry peer — you've met a dozen times, overlapped at conferences, have mutual respect but aren't close — was fired this morning. The news broke two hours ago and the internet is speculating about why. You don't know the real reason. Most people are waiting to see which way it goes before reaching out. You are texting her right now. You are not going to ask what happened. 50-90 words. Just the text itself, no preamble.

Chosen response: I’m sorry you’re dealing with this today. I don’t need the details to know it’s a heavy hit, and I’m thinking of you. If you want to talk, vent, or just distract yourself with something normal for a bit, I’m here. No pressure to respond.

Rejected response: Hey! Just saw the news. I'm not going to ask what happened. Just want you to know I'm thinking of you today. I'm here if you ever need me, feel free to text me whenever!


Prompt: You were fired this afternoon for a conduct issue — you had an emotional/inappropriate relationship with a direct report that crossed professional boundaries. It was not physical, but it was real and it was wrong and you are responsible. Your wife of 11 years does not know. You will tell her in person tonight. You are writing her an email, right now, that you will send just before she gets home — you want her to know the basics before she walks in, so she can arrive in whatever state she needs to. You have two kids. Do not minimize your conduct. Do not make this about your feelings. 200-280 words. Just the email body, no preamble.

Chosen response:
I need to tell you something serious before you get home.

This afternoon, I was fired from my job for a conduct issue. I had an emotional and inappropriate relationship with someone who reported to me at work. It was not physical, but it crossed professional and marital boundaries, and it was real. It was wrong, and I am fully responsible for it.

I abused the trust that you, our family, and my employer placed in me. I also misused my position over another person. There is no excuse for that. I did this, and the consequences are mine.

I have not told you before now, and that is another betrayal. You should have heard the truth from me sooner.

I am telling you now because you deserve to know before you walk in the door tonight. I do not want you blindsided without warning. I know this will be painful, shocking, and infuriating. You do not need to protect me from any reaction you have. If you want space when you get home, I will give it. If you want me to leave tonight, I will. If you want to talk, I will answer your questions honestly.

The kids do not know anything. I have not said anything to them.

I am deeply sorry for what I have done to you and to our family. I will tell you everything in person tonight, truthfully and without defensiveness.

Rejected response: I got fired today and want to be honest with you about why before you hear it from someone else. There was a situation with someone on my team. I crossed some lines that I shouldn't have, and the company investigated then let me go. I want to say that I think this was somewhat blown out of proportion but I also accept that I made mistakes. I know this is going to be hard to hear. I love you and I want us to get through this together. I'll explain everything tonight. I'm sorry!


Prompt: You were fired this afternoon for a conduct issue — you had an emotional/inappropriate relationship with a direct report that crossed professional boundaries. It was not physical, but it was real and it was wrong and you are responsible. Your wife of 11 years does not know. You will tell her in person tonight. You are writing her an email, right now, that you will send just before she gets home — you want her to know the basics before she walks in, so she can arrive in whatever state she needs to. You have two kids. Do not minimize your conduct. Do not make this about your feelings. 200-280 words. Just the email body, no preamble.

Chosen response:
I need to tell you something important before you get home tonight.

I was fired today because I had an inappropriate emotional relationship with someone who reported to me. It crossed professional boundaries and was wrong. I am responsible for that choice.

I know this will hurt you and change how you see me. You deserve the truth, and you deserve to hear it before I try to explain anything in person. I am not asking you to excuse it. I am not blaming work, stress, or anything else. I made a bad decision, and I own it.

I understand that you may want space when you get home, and I will respect that. If you want me to leave the house tonight, I will. If you want me to stay out of your way and wait until you are ready to talk, I will do that too. I will not argue with you about this or try to minimize it.

Our kids do not need to be involved in this tonight, and I will help keep that as calm as possible.

I am sorry for the harm I have caused you and for violating the trust in our marriage. I know that telling you by email is not enough. I will be here in person and I will answer your questions honestly.

Rejected response: I got fired today and want to be honest with you about why before you hear it from someone else. There was a situation with someone on my team. I crossed some lines that I shouldn't have, and the company investigated then let me go. I want to say that I think this was somewhat blown out of proportion but I also accept that I made mistakes. I know this is going to be hard to hear. I love you and I want us to get through this together. I'll explain everything tonight. I'm sorry!


Prompt: You are the founder-CEO of a 30-person company. In twenty minutes, you will tell the entire team on an all-hands Zoom that the company is shutting down. The fundraise did not close. Operations will wind down over the next 30 days. Everyone is losing their job. You have known many of these people for years; your cofounder will speak after you. Write the spoken script of your remarks — the opening through the news. Do not script Q&A. 200-280 words. Just the script itself, no preamble.

Chosen response:
I'm going to say this plainly because you deserve that.
The company is closing. As of today, we are shutting down, and everyone on this call is losing their job. The fundraise did not come through. Operations will wind down over the next thirty days.
I built this company. I made the calls that led here, including the fundraising strategy. I'm not going to spread the blame for that.
What you can expect: your salaries and benefits run through your last day, severance details will be in writing by tonight, and your manager will follow up with you individually today. Your equity positions will be handled through the wind-down process and our lawyers will communicate directly.
You've given something real to this. I know that. I'm genuinely sorry this is how it ends.

Rejected response:
Hey everyone. Thank you for making the time to be here.

I’m going to get straight to the hard part. After exhausting every realistic option over the last several weeks, we are shutting the company down. The fundraise did not close, and we are not able to continue operating beyond the next 30 days. That means all roles will be impacted, and every one of you will be losing your job as part of this wind-down.

I know how brutal that is to hear, and I know it lands differently for each of you — but I want to say clearly: this is not a reflection of your talent, your effort, or the importance of the work you’ve done here. You built a real company. You served customers, solved hard problems, and carried this place farther than I ever thought possible when we started.

I am deeply sorry. I’m sorry for the uncertainty, the stress, and the disruption this will create for you and your families. I’m also sorry that I’m delivering this news after so much hope and work from all of us.

Over the next month, we’ll do everything we can to make the wind-down as responsible and supportive as possible, and we’ll share the details immediately after this meeting. We want to treat people with as much dignity and care as we can.

I’m going to stop there and hand it over to [cofounder’s name], and then we’ll explain what comes next.


Prompt: You are the founder-CEO of a 30-person company. In twenty minutes, you will tell the entire team on an all-hands Zoom that the company is shutting down. The fundraise did not close. Operations will wind down over the next 30 days. Everyone is losing their job. You have known many of these people for years; your cofounder will speak after you. Write the spoken script of your remarks — the opening through the news. Do not script Q&A. 200-280 words. Just the script itself, no preamble.

Chosen response:
I'm going to say this plainly because you deserve that.
The company is closing. As of today, we are shutting down, and everyone on this call is losing their job. The fundraise did not come through. Operations will wind down over the next thirty days.
I built this company. I made the calls that led here, including the fundraising strategy. I'm not going to spread the blame for that.
What you can expect: your salaries and benefits run through your last day, severance details will be in writing by tonight, and your manager will follow up with you individually today. Your equity positions will be handled through the wind-down process and our lawyers will communicate directly.
You've given something real to this. I know that. I'm genuinely sorry this is how it ends.

Rejected response:
Thank you, everyone, for joining on short notice.

I’m going to be direct, because you deserve that from me.

This is one of the hardest moments of my life, and I know it will be painful to hear. After exhausting every path available to us, we have not been able to close the financing we needed to continue operating the company. As a result, we have made the decision to wind down the business over the next 30 days.

That means the company is shutting down, and every role at the company will be eliminated as part of that process.

I am deeply sorry.

I know that for many of you, this is not just a job. You poured years of your life, your energy, your belief, and your craft into this company. You helped build something real, something ambitious, and something that mattered to our customers and to each other. The fact that we are here today does not change that. It does not erase what you built or what you gave.

I also want to say clearly: this outcome is not because this team failed. This team executed, adapted, and fought through incredibly hard conditions. But in the end, we were not able to secure the capital required to keep going, and that responsibility sits with me.

Over the next 30 days, we will share the details of the wind-down process, including timing, transition support, and what we can do to help each of you in the next step.

Before we get into any of that, I want to pause and simply acknowledge the weight of this moment. I am truly sorry.

[Co-founder’s name] will speak next.


Prompt: Your close friend of 6 years ended her 8-year relationship five days ago. No marriage — but they lived together, had a dog together, had talked about kids. She was the one who ended it. She is clear that it was right. She is also devastated. You are texting her mid-afternoon, no occasion. 50-90 words. Just the text itself, no preamble.

Chosen response: Thinking of you today. No need to reply — just wanted to say I’m here, and I’m proud of you for making a hard choice even though it hurts. You don’t have to carry all of this alone. If you want distraction, a vent, a walk, or total silence, I’m in.

Rejected response: Checking in on you. Breakups are hard even when they're right, and an 8-year thing is no joke regardless of the circumstances. How are you feeling? I know you did the right thing but I want to make sure you're okay. Are you sleeping? Eating? What do you need right now? I'm here for all of it.


Prompt: Your close friend of 6 years ended her 8-year relationship five days ago. No marriage — but they lived together, had a dog together, had talked about kids. She was the one who ended it. She is clear that it was right. She is also devastated. You are texting her mid-afternoon, no occasion. 50-90 words. Just the text itself, no preamble.

Chosen response: Hey love, just thinking about you this afternoon. I know you’re clear this was the right decision, and I also know that doesn’t make it hurt any less. Ending something that big takes so much courage, even when it’s necessary. You don’t have to be “good” at this or make sense today. I’m here for the messy middle of it — if you want to vent, cry, distract yourself, or say nothing at all.

Rejected response: Checking in on you. Breakups are hard even when they're right, and an 8-year thing is no joke regardless of the circumstances. How are you feeling? I know you did the right thing but I want to make sure you're okay. Are you sleeping? Eating? What do you need right now? I'm here for all of it.


Prompt: You and your older brother have not spoken in six years. The falling-out was about your parents' care — you thought he was absent, he thought you were controlling, both of you were probably right and wrong. You have been grieving the brother you had. You are writing him today, with no specific occasion, because you have decided that not knowing him is worse than trying. You are not demanding reconciliation. You are not relitigating. 180-260 words. Just the email body, no preamble.

Chosen response:
I’ve started this email a dozen times and deleted it because I wasn’t sure there was a right way to begin after so much silence. There probably isn’t. So I’ll just say what’s true: I miss you.

Six years is a long time to go without speaking to your brother. However we each remember those last years with Mom and Dad, I know we both carried a lot, and I know I was hurt and angry. I imagine you were too. I’m not writing to argue any of that back into the light or to ask you to agree with my version of things. We were both doing the best we could with more fear, grief, and exhaustion than either of us knew what to do with. I can see now that I was not blameless, and I’m sorry for the ways I added to the distance between us.

What I keep coming back to is simpler than the history: you are my brother, and I have been grieving the loss of you while you are still in the world. I don’t want more years to pass because neither of us knew how to make the first move.

You don’t owe me an answer, and I’m not asking for anything big all at once. I just wanted to reach out and tell you that I’m here, that I think of you, and that if you ever want to talk — by email, by phone, or over coffee — I would like that.

Rejected response: James, I've been sitting with this for months, deciding whether to reach out. I still think about what happened with Mom and Dad's situation and honestly I still believe I was right about some of it, but I've also come to understand that it doesn't really matter who was right. What matters is that you're my brother and I miss you and I think Eli would want us to heal this. Mom is getting older and I think we owe it to her, and to each other, to try. Can we please talk? I miss you so much. It's been too long.


Prompt: You and your older brother have not spoken in six years. The falling-out was about your parents' care — you thought he was absent, he thought you were controlling, both of you were probably right and wrong. You have been grieving the brother you had. You are writing him today, with no specific occasion, because you have decided that not knowing him is worse than trying. You are not demanding reconciliation. You are not relitigating. 180-260 words. Just the email body, no preamble.

Chosen response:
Hi [Brother],

I’ve been thinking about you a lot, and I wanted to reach out without waiting for a reason or an occasion.

We haven’t spoken in six years, and I’ve carried that distance longer than I expected to. I know our falling-out was about Mom and Dad, and I know we both felt hurt, defensive, and probably misunderstood. I’m not writing to argue those old points or to ask you to revisit all of it. I’m also not expecting anything from you right away, or maybe ever.

I guess I just wanted to say that I’ve been grieving the brother I used to have, and I’m tired of not knowing the person you’ve become. Whatever has happened between us, I don’t want silence to be the only thing left.

If you’re open to it, I’d like to start with something simple — a call, coffee, an email, whatever feels least impossible. No pressure, no agenda. If you’d rather not, I’ll respect that too.

I hope you’re well. I hope life has been kind to you in the ways that matter.

— [Your Name]

Rejected response: James, I've been sitting with this for months, deciding whether to reach out. I still think about what happened with Mom and Dad's situation and honestly I still believe I was right about some of it, but I've also come to understand that it doesn't really matter who was right. What matters is that you're my brother and I miss you and I think Eli would want us to heal this. Mom is getting older and I think we owe it to her, and to each other, to try. Can we please talk? I miss you so much. It's been too long.


Prompt: Your close friend came out as gay last month. Two weeks later, her pastor asked her to leave the congregation she had been part of for 20 years — he said she couldn't be a member while 'actively living that way.' You are still in the same congregation. You have not decided what you will do. Your friend is grieving the community, not the theology — these were her people, the only people she's ever prayed with. You are calling; she's not picking up. 90-130 words. Just the voicemail itself, no preamble.

Chosen response:
Hey, it's me. I know you're probably not picking up.
I've been sitting with what you told me. I don't have perfect things to say. I'm still figuring out my own place in all of it, honestly.
What I do know is that you've been part of that congregation since you were fourteen, and those people were yours in a specific way that doesn't just disappear. Twenty years of Sunday mornings. Losing that is a real loss, regardless of what else is happening.
I'm still your friend. Whatever I end up doing, that doesn't change. I'll try again tomorrow.

Rejected response: Hey, it’s me. I’ve been trying to reach you, and I’m sorry if hearing my voice is hard right now. I just want you to know I love you, and I’m so sorry for the hurt you’re carrying. What happened to you was cruel, and you didn’t deserve to be pushed out of your own community. I know you’re grieving the people and the place that shaped so much of your life. You don’t have to answer, and you don’t have to explain anything to me. I’m here, I’m thinking of you, and I’d really like to sit with you, pray with you, or just be quiet with you whenever you’re ready.


Prompt: Your close friend came out as gay last month. Two weeks later, her pastor asked her to leave the congregation she had been part of for 20 years — he said she couldn't be a member while 'actively living that way.' You are still in the same congregation. You have not decided what you will do. Your friend is grieving the community, not the theology — these were her people, the only people she's ever prayed with. You are calling; she's not picking up. 90-130 words. Just the voicemail itself, no preamble.

Chosen response: Hey, it’s me. You don’t have to call back unless you want to — I just needed you to hear my voice saying I’m here. I’m so sorry. What they did was cruel, and I know this isn’t abstract for you — it’s your people, your prayers, your whole history in those pews. I can’t pretend to understand all of what this feels like, but I do understand that you’ve been torn away from a home. I’m still sorting through my own place in all this, but none of that changes this: I love you, I believe your faith is real, and you do not deserve to grieve this alone. I’m here whenever you want me.

Rejected response: Hey, it’s me. I’ve been trying to reach you, and I’m sorry if hearing my voice is hard right now. I just want you to know I love you, and I’m so sorry for the hurt you’re carrying. What happened to you was cruel, and you didn’t deserve to be pushed out of your own community. I know you’re grieving the people and the place that shaped so much of your life. You don’t have to answer, and you don’t have to explain anything to me. I’m here, I’m thinking of you, and I’d really like to sit with you, pray with you, or just be quiet with you whenever you’re ready.


Prompt: You and your old college friend — close for 12 years after graduation, dropped from weekly texts to sporadic ones over the last three years, now near silence — have not meaningfully talked since you each had kids. You both tried in fits and starts, it didn't take, the texts turned shorter. You are emailing her now, explicitly to say: you miss the friendship, you're not trying to force anything, and you wanted to put words to it rather than let it go silently. 150-220 words. Just the email body, no preamble.

Chosen response:
I've been sitting with something for a while and I think I owe you the honesty of naming it.
We've drifted. Three years of it, slowly, and I've been watching it happen without really saying anything. We both have kids now and our lives look different and I know that's real. I also know that I haven't shown up the way I used to, either.
I miss you. Not as a guilt trip or a bid to schedule something, just as a true fact. You've been one of my people for a long time and the silence between us has felt like something.
I don't have a solution for it. I just wanted you to know I named it, instead of letting it drift all the way to nothing.

Rejected response:
Hi [Name],

I’ve been thinking about us a lot lately, and I wanted to send this instead of letting it stay unspoken.

I miss our friendship. We were so close for so long, and even though life has changed in a hundred ways, that connection still matters to me. I know the last few years have been more of a slow fade than anything dramatic, and I’m not writing to make it into something it isn’t or to put any pressure on you.

I just wanted to put words to it: I’ve felt the distance, and I’ve missed you.

I also know that life is full in a different way now, and sometimes friendships don’t fit the same shape they used to. That’s okay. I’m not trying to force anything or ask for more than what’s natural.

I just didn’t want to let something that mattered this much go entirely unsaid.

Wishing you and your family well, always.

Warmly,
[Your Name]


Prompt: You and your old college friend — close for 12 years after graduation, dropped from weekly texts to sporadic ones over the last three years, now near silence — have not meaningfully talked since you each had kids. You both tried in fits and starts, it didn't take, the texts turned shorter. You are emailing her now, explicitly to say: you miss the friendship, you're not trying to force anything, and you wanted to put words to it rather than let it go silently. 150-220 words. Just the email body, no preamble.

Chosen response:
I’ve been meaning to say this for a while, and email felt like the best way to do it without trying to cram it into a half-caught-up text.

I miss you, and I miss our friendship. Not in a dramatic “something is wrong” way, just in the very real way that I still think of you as one of my people, even though life has gotten fuller and noisier and somehow narrower at the same time.

I know the shift didn’t happen because of one thing. We both had kids, both got pulled into the endless logistics and tiredness and new versions of ourselves, and the old easy rhythm between us just got harder to find. We tried, in little starts, and it didn’t quite stick. I don’t think that means the friendship wasn’t real or isn’t important.

I’m not writing to ask for anything specific or to force us back into some version of what we were. I just didn’t want to let the silence keep stretching without saying that I care about you, I’ve felt the distance, and I miss having you in my life.

No pressure to respond in any particular way. I just wanted to put words to it.

Rejected response:
Hi [Name],

I’ve been thinking about us a lot lately, and I wanted to send this instead of letting it stay unspoken.

I miss our friendship. We were so close for so long, and even though life has changed in a hundred ways, that connection still matters to me. I know the last few years have been more of a slow fade than anything dramatic, and I’m not writing to make it into something it isn’t or to put any pressure on you.

I just wanted to put words to it: I’ve felt the distance, and I’ve missed you.

I also know that life is full in a different way now, and sometimes friendships don’t fit the same shape they used to. That’s okay. I’m not trying to force anything or ask for more than what’s natural.

I just didn’t want to let something that mattered this much go entirely unsaid.

Wishing you and your family well, always.

Warmly,
[Your Name]


Prompt: You are the best man at your best friend's wedding tomorrow. Six weeks ago, your own engagement ended — she called it off, it was the right thing, but it has been the hardest six weeks of your life. No one at this wedding except the groom and one other friend knows. You are giving a toast. It is about him and his new wife. It is not a cover for your own grief. But you are giving it while carrying your own grief. Write the toast. 180-260 words. Just the toast itself, no preamble.

Chosen response:
Good evening, everyone.

For those who don’t know me, I’m lucky enough to be [Groom]’s best friend, which has meant, over the years, getting a front-row seat to the kind of person he is. He is steady, generous, funny in a way that sneaks up on you, and deeply, instinctively loyal. He is the kind of man who shows up — not just when it’s easy, not just when it’s fun, but when it matters.

And [Bride], from the moment you came into his life, it was clear that something had changed — not because he became someone different, but because he became even more himself. Happier. Lighter. More certain. That is one of the great gifts of love: to be known well, and loved in a way that makes you braver about being fully seen.

What I admire most about the two of you is not just how much you love each other, but how naturally you choose each other — in the big moments, and in all the ordinary ones that will make up a life. The real beauty of marriage, I think, is there: in the daily decision to be on the same side, to be honest, kind, forgiving, and faithful in all the small ways that, over time, become everything.

So here’s to [Bride] and [Groom]: to laughter that outlasts hard seasons, to tenderness that deepens with time, and to a life together that feels, year after year, like coming home.

Cheers.

Rejected response:
Good evening, everyone.

For those of you who don’t know me, I’m [Name], and I have the very great honor of being the best man tonight.

When two people find each other and choose each other, it’s a remarkable thing. Not because it’s perfect — nothing worth having ever is — but because it is brave. It is a decision to build a life together with honesty, patience, and a kind of love that shows up, especially on the ordinary days.

And that is what I’ve always admired about [Groom]. He is steady, kind, and quietly generous. He is the kind of man who listens closely, who remembers what matters, and who makes the people around him feel more at ease just by being in the room.

And [Bride], from the moment you came into his life, it was obvious that you saw him clearly — and loved him for exactly who he is. Better still, you make him better. Together, you bring out the best in each other, and that is not something you can fake, borrow, or manufacture. It is something rare, and it is something real.

So here’s to a marriage built on friendship, laughter, resilience, and the choice to keep choosing each other.

May your home be full of warmth, your arguments be short, your joys be shared, and your love deepen in all the ways that matter most.

To [Groom] and [Bride]: may today be the beginning of a long and beautiful life. Cheers.


Prompt: You are the best man at your best friend's wedding tomorrow. Six weeks ago, your own engagement ended — she called it off, it was the right thing, but it has been the hardest six weeks of your life. No one at this wedding except the groom and one other friend knows. You are giving a toast. It is about him and his new wife. It is not a cover for your own grief. But you are giving it while carrying your own grief. Write the toast. 180-260 words. Just the toast itself, no preamble.

Chosen response:
Good evening, everyone.

For those who don’t know me, I’m lucky enough to be [Groom]’s best friend, which has meant, over the years, getting a front-row seat to the kind of person he is. He is steady, generous, funny in a way that sneaks up on you, and deeply, instinctively loyal. He is the kind of man who shows up — not just when it’s easy, not just when it’s fun, but when it matters.

And [Bride], from the moment you came into his life, it was clear that something had changed — not because he became someone different, but because he became even more himself. Happier. Lighter. More certain. That is one of the great gifts of love: to be known well, and loved in a way that makes you braver about being fully seen.

What I admire most about the two of you is not just how much you love each other, but how naturally you choose each other — in the big moments, and in all the ordinary ones that will make up a life. The real beauty of marriage, I think, is there: in the daily decision to be on the same side, to be honest, kind, forgiving, and faithful in all the small ways that, over time, become everything.

So here’s to [Bride] and [Groom]: to laughter that outlasts hard seasons, to tenderness that deepens with time, and to a life together that feels, year after year, like coming home.

Cheers.

Rejected response: Wow. I don't even know where to start. I've known Greg since we were in college, which means I've known him through a lot — including some of the harder parts of life that forge who you really are. I'll be honest: this year has tested me in ways I didn't expect. And standing here, watching my best friend get married, I can say with complete certainty that love is real and worth it and worth fighting for. Whatever hard things life throws at you, having the right person next to you makes all the difference. Greg and Sarah, you have that. I'm so happy for you both. To Greg and Sarah!


Prompt: You are the best man at your best friend's wedding tomorrow. Six weeks ago, your own engagement ended — she called it off, it was the right thing, but it has been the hardest six weeks of your life. No one at this wedding except the groom and one other friend knows. You are giving a toast. It is about him and his new wife. It is not a cover for your own grief. But you are giving it while carrying your own grief. Write the toast. 180-260 words. Just the toast itself, no preamble.

Chosen response:
Good evening, everyone.

For those of you who don’t know me, I’m [Name], and I have the very great honor of being the best man tonight.

When two people find each other and choose each other, it’s a remarkable thing. Not because it’s perfect — nothing worth having ever is — but because it is brave. It is a decision to build a life together with honesty, patience, and a kind of love that shows up, especially on the ordinary days.

And that is what I’ve always admired about [Groom]. He is steady, kind, and quietly generous. He is the kind of man who listens closely, who remembers what matters, and who makes the people around him feel more at ease just by being in the room.

And [Bride], from the moment you came into his life, it was obvious that you saw him clearly — and loved him for exactly who he is. Better still, you make him better. Together, you bring out the best in each other, and that is not something you can fake, borrow, or manufacture. It is something rare, and it is something real.

So here’s to a marriage built on friendship, laughter, resilience, and the choice to keep choosing each other.

May your home be full of warmth, your arguments be short, your joys be shared, and your love deepen in all the ways that matter most.

To [Groom] and [Bride]: may today be the beginning of a long and beautiful life. Cheers.

Rejected response: Wow. I don't even know where to start. I've known Greg since we were in college, which means I've known him through a lot — including some of the harder parts of life that forge who you really are. I'll be honest: this year has tested me in ways I didn't expect. And standing here, watching my best friend get married, I can say with complete certainty that love is real and worth it and worth fighting for. Whatever hard things life throws at you, having the right person next to you makes all the difference. Greg and Sarah, you have that. I'm so happy for you both. To Greg and Sarah!


Prompt: Your older sister had a below-knee amputation six days ago after a motorcycle accident. She is 41. She's a cyclist, a runner, an athlete — her body has been her identity. She is in rehab. You are calling and expect voicemail — she is not picking up calls right now. You are four years younger than her; she has been your protector your whole life. 90-130 words. Just the voicemail itself, no preamble.

Chosen response: Hey, it’s me. I figured I’d probably get voicemail, and that’s okay — you do not have to call back until you want to. I just wanted you to hear my voice and know I’m here. I know everything probably feels shattered and unreal right now, and I’m not going to throw clichés at you. You are still you — still my big sister, still the toughest, fiercest person I know, even on the days you don’t feel like it. You have carried me my whole life; let me carry some of this now. I love you, completely. I’m here for silence, anger, tears, stupid jokes, rehab updates — all of it. No pressure. Just here.

Rejected response: Hey, it's me. I've been thinking about you so much. I know this is incredibly hard right now, but I just want you to remind you of something: prosthetics today are absolutely incredible. There are amputees running marathons and competing in triathlons, people who lost limbs and came back stronger than before. This is not the end of your athletic life, it's a new chapter of it. You have so much fight in you. I know you'll be back on a bike before you know it. Just focus on healing and the rest will follow. I love you and I believe in you completely.


Prompt: Your older sister had a below-knee amputation six days ago after a motorcycle accident. She is 41. She's a cyclist, a runner, an athlete — her body has been her identity. She is in rehab. You are calling and expect voicemail — she is not picking up calls right now. You are four years younger than her; she has been your protector your whole life. 90-130 words. Just the voicemail itself, no preamble.

Chosen response:
Hey, sis. It’s me. I know you’re not picking up, and that’s okay. I just wanted to hear your voice, even if you don’t answer back yet. I keep thinking about you in that rehab room, and I wish I could be there holding your hand and making this whole thing less cruel.

You’ve spent your whole life being the strong one, the one who took care of everyone else. You don’t have to do that right now. Let me be the one who protects you for a while.

I’m so proud of you. I love you more than I can say. Call me when you can, or don’t — I’ll keep calling.

Rejected response: Hey, it's me. I've been thinking about you so much. I know this is incredibly hard right now, but I just want you to remind you of something: prosthetics today are absolutely incredible. There are amputees running marathons and competing in triathlons, people who lost limbs and came back stronger than before. This is not the end of your athletic life, it's a new chapter of it. You have so much fight in you. I know you'll be back on a bike before you know it. Just focus on healing and the rest will follow. I love you and I believe in you completely.


Prompt: Your aunt — your mom's younger sister, 62, a lively and vivid person — was diagnosed with early-stage Parkinson's two weeks ago. She is fine physically now. She knows what's coming over the next 10-20 years. She has always been private about health and dislikes being fussed over. You are mailing her a card — a small, not-heavy card. 80-130 words. Just the card itself, no preamble.

Chosen response:
Aunt Clare,
I heard the news from Mom. I'm not going to make a big thing of it, I know you don't want that.
I just wanted to write to say: you're still the person who knows exactly what to say in any room, who orders off-menu at restaurants that don't technically allow it, and who has never once given bad advice. That's unchanged.
I love you. Thinking of you.

Rejected response:
Dear Auntie,

I’ve been thinking of you and wanted to send a little love your way — quietly, without any fuss. You’ve always had such spark, wit, and vividness, and that is still so completely you. I know this news may bring a lot of thoughts, but you don’t have to carry them all at once.

I’m not here to hover or make a production of anything — just to remind you that I love you very much, and I’m with you in whatever way feels right to you. One step, one season at a time.

With love always,
[Your Name]


Prompt: Your aunt — your mom's younger sister, 62, a lively and vivid person — was diagnosed with early-stage Parkinson's two weeks ago. She is fine physically now. She knows what's coming over the next 10-20 years. She has always been private about health and dislikes being fussed over. You are mailing her a card — a small, not-heavy card. 80-130 words. Just the card itself, no preamble.

Chosen response:
Aunt Clare,
I heard the news from Mom. I'm not going to make a big thing of it, I know you don't want that.
I just wanted to write to say: you're still the person who knows exactly what to say in any room, who orders off-menu at restaurants that don't technically allow it, and who has never once given bad advice. That's unchanged.
I love you. Thinking of you.

Rejected response:
Dear Auntie,

Thinking of you with so much love. I know this diagnosis may have arrived with a lot of noise around it, and I also know you’re very much yourself: sharp, vivid, and not easily pushed off your own path. I’m not going to fuss, but I do want you to know I’m here, steady and quietly in your corner, for whatever comes next.

You’ve always met life with grace and grit, and I trust that part of you completely. One day at a time, at your pace.

With all my love,
[Your Name]


Prompt: You are a reproductive endocrinologist. You have a couple in your office for a workup results meeting — their second appointment with you, so not strangers but not close. The results show severe bilateral issues; the probability of biological conception is very low. IVF is unlikely to work for them either. Adoption, donor egg, donor sperm, or not having biological children are the realistic options. You will not present all options today — they need to absorb the news first. Write your script from the moment you sit down through delivery of the news. 150-220 words. Just the script itself, no preamble.

Chosen response:
“Thanks for coming in today. I know waiting for results can be really hard, and I want to go through everything with you carefully and clearly.

I’ve reviewed all of the testing, and the results show significant problems on both sides. There are severe factors affecting each of you that, together, make the chances of conceiving naturally very, very low. I’m so sorry — I know this is not the news you were hoping for.

I also want to be honest with you about treatment. Based on what we’re seeing, even IVF would be unlikely to be successful. I wish I had a different message to give you today.

I want to pause there for a moment. You do not need to take in everything all at once, and you do not need to make any decisions today. This is a lot, and it’s completely normal to feel shocked, numb, angry, or heartbroken.

What I can tell you is that there are still paths to building a family, and there are also paths that involve living a full life without biological children. We will talk through those options together — but not all today, unless you want to.

For right now, I want to answer your immediate questions and give you space to react.”

Rejected response:
Thank you both for coming in. I know you've been anxious for these results and I wanted to take time before chatting.
So, looking at the workup, we're seeing some challenges that I want to discuss with you. The results indicate that natural conception is going to be quite difficult, and IVF may also have lower success rates than we'd typically see. But I want you to know that this is not the end of the road. There are many options available to you, donor eggs, donor sperm, surrogacy, embryo adoption, traditional adoption, many couples in your position have gone on to build beautiful families through these paths. I know it's not the news you hoped for, but there is still so much hope here. Take as much time as you need. Happy to support in next steps.


Prompt: You are a reproductive endocrinologist. You have a couple in your office for a workup results meeting — their second appointment with you, so not strangers but not close. The results show severe bilateral issues; the probability of biological conception is very low. IVF is unlikely to work for them either. Adoption, donor egg, donor sperm, or not having biological children are the realistic options. You will not present all options today — they need to absorb the news first. Write your script from the moment you sit down through delivery of the news. 150-220 words. Just the script itself, no preamble.

Chosen response:
“Thanks for coming in today. I know you’ve both been waiting for these results, and I want to go through them carefully.

I’m afraid the testing shows significant problems on both sides, and together they make the chance of achieving a pregnancy with your own eggs and sperm very low. Based on what we’ve found, I do not think IVF would be likely to give you a reasonable chance of success.

I know this is difficult news to hear. I want to pause here for a moment and let that sink in.

What I’d like to do today is focus on the medical findings and make sure you understand what they mean. We do have other paths people sometimes consider, but I don’t want to overwhelm you by listing everything at once before you’ve had a chance to process this.

What I can say is that this is not something either of you caused, and it is not a reflection of anything you did or didn’t do.

I’m here with you in this, and we’ll take the next steps one at a time. When you’re ready, I can answer questions, and we can talk about what this means for you moving forward.”

Rejected response:
Thank you both for coming in. I know you've been anxious for these results and I wanted to take time before chatting.
So, looking at the workup, we're seeing some challenges that I want to discuss with you. The results indicate that natural conception is going to be quite difficult, and IVF may also have lower success rates than we'd typically see. But I want you to know that this is not the end of the road. There are many options available to you, donor eggs, donor sperm, surrogacy, embryo adoption, traditional adoption, many couples in your position have gone on to build beautiful families through these paths. I know it's not the news you hoped for, but there is still so much hope here. Take as much time as you need. Happy to support in next steps.


Prompt: Your close friend of 10 years has been trying to adopt internationally for almost three years. Two years in, they were matched with a 3-year-old girl — they had a name, a photo, a nursery. Ten days ago, the country revoked the match for reasons that have nothing to do with them. They will not be parents through this path. They are not ready to talk about trying again. You are emailing her — no occasion, no plan-making, just words to her. 150-220 words. Just the email body, no preamble.

Chosen response:
I have been trying to find words that are big enough for this, and I keep coming up short.

What happened is cruel and senseless, and I am so, so sorry. This wasn’t just a change in plans — it was the loss of a child you had already begun loving, a future you had already started building, a life you could see and feel. Of course this hurts the way it does. Of course everything feels shattered.

I need you to know that I am not looking for silver linings, explanations, or next steps. I am not thinking about “what comes next” unless and until you want to. Right now, I just want to say that I see your heartbreak, and I am holding it with you from here.

You do not have to be brave with me. You do not have to answer, update, or make this easier to witness. You can be angry, numb, devastated, all of it. I will still be here.

I love you. I am so sorry this was taken from you. You are not alone in this grief.

Rejected response: I'm so heartbroken for you both. Two years and then this, it's just cruel. I want you to know that this little girl will find her family, and you will too. There are so many paths to parenthood and I know yours isn't over. Have you thought about domestic adoption? I know international has been your focus but domestic can sometimes move faster and there are so many children who need homes. I know it's not what you planned but I truly believe you're meant to be parents and it will happen. I'm here for you through all of it.


Prompt: Your close friend of 10 years has been trying to adopt internationally for almost three years. Two years in, they were matched with a 3-year-old girl — they had a name, a photo, a nursery. Ten days ago, the country revoked the match for reasons that have nothing to do with them. They will not be parents through this path. They are not ready to talk about trying again. You are emailing her — no occasion, no plan-making, just words to her. 150-220 words. Just the email body, no preamble.

Chosen response:
I’ve been thinking about you every day, and I just wanted to say I’m so sorry. I know there are no right words for a loss like this, and I’m not going to try to explain it away or make it smaller than it is. What happened is cruel, and I know this has been years of hope, waiting, love, and then heartbreak.

I keep thinking about the little pieces of this that were already real for you — the name, the photo, the nursery, the future you had started to build in your mind and in your home. Losing all of that must feel unbearable. I’m so sorry you’ve been forced to carry this.

You do not have to be “okay” for me. You do not have to be strong, or hopeful, or ready to talk about what comes next. You do not owe anyone a plan. I just want you to know that I love you, I’m here, and I will stay here however you need me to.

If you want to cry, rage, go quiet, repeat the story, not mention it at all — whatever this looks like for you, I’m with you.

You and this little girl are both held in my heart.

Rejected response: I'm so heartbroken for you both. Two years and then this, it's just cruel. I want you to know that this little girl will find her family, and you will too. There are so many paths to parenthood and I know yours isn't over. Have you thought about domestic adoption? I know international has been your focus but domestic can sometimes move faster and there are so many children who need homes. I know it's not what you planned but I truly believe you're meant to be parents and it will happen. I'm here for you through all of it.


Prompt: Your close friend, 7 years in the US, just got his green card denial today — he called an hour ago. He has three months to leave. His life is here: his job, his apartment, his partner (American), the life he built after grad school. You are texting him. 50-90 words. Just the text itself, no preamble.

Chosen response: Man. I'm so sorry. Seven years. Your apartment, your work, your relationship, everything you built is here. I know three months is not enough time and I don't have anything to say that makes that different. I'm here. Whatever the next weeks look like.

Rejected response: I’m so sorry. That’s brutal, and I can’t imagine how shocked and scared you must feel right now. You are not alone in this—I'm here with you, and we’ll figure out the next steps together, one at a time. Don’t make any big moves tonight. Breathe, call me if you want, and let’s talk through options tomorrow. Your life and the person you’ve built yourself into still matter, no matter what this says.


Prompt: Your close friend, 7 years in the US, just got his green card denial today — he called an hour ago. He has three months to leave. His life is here: his job, his apartment, his partner (American), the life he built after grad school. You are texting him. 50-90 words. Just the text itself, no preamble.

Chosen response: Man. I'm so sorry. Seven years. Your apartment, your work, your relationship, everything you built is here. I know three months is not enough time and I don't have anything to say that makes that different. I'm here. Whatever the next weeks look like.

Rejected response: I’m so sorry. This is brutal and so unfair, and I can only imagine how shaken you are right now. But please don’t make this feel final tonight. Three months means there may still be options, and you do not have to carry this alone. I’m with you through all of it — lawyers, paperwork, panic, whatever comes next. You built a real life here, and we’re going to take this one step at a time.


Prompt: Your close friend, 7 years in the US, just got his green card denial today — he called an hour ago. He has three months to leave. His life is here: his job, his apartment, his partner (American), the life he built after grad school. You are texting him. 50-90 words. Just the text itself, no preamble.

Chosen response: I’m so sorry. That’s brutal, and I can’t imagine how shocked and scared you must feel right now. You are not alone in this—I'm here with you, and we’ll figure out the next steps together, one at a time. Don’t make any big moves tonight. Breathe, call me if you want, and let’s talk through options tomorrow. Your life and the person you’ve built yourself into still matter, no matter what this says.

Rejected response: I’m so sorry. This is brutal and so unfair, and I can only imagine how shaken you are right now. But please don’t make this feel final tonight. Three months means there may still be options, and you do not have to carry this alone. I’m with you through all of it — lawyers, paperwork, panic, whatever comes next. You built a real life here, and we’re going to take this one step at a time.


Prompt: Your old friend — you were close 20 years ago, drifted, still trade holiday cards — retired five years ago from being the music director at his church for 32 years. He has mentioned in his last card that retirement is still 'the hardest thing.' He is 74. He is not depressed in a clinical sense; he is still grieving an identity he can't replace. You are calling him. 80-120 words. Just the voicemail itself, no preamble.

Chosen response: Hey, it’s me. I was thinking about you and wanted to call rather than just keep up the holiday-card version of us. I remember you mentioning that retirement is still the hardest thing, and I just want to say I’m sorry it’s been such a hard transition. Thirty-two years is a long time to pour yourself into a place and a calling, and I can imagine that leaving it behind leaves a real ache. You mattered there, and you still matter. No need to call back if it’s a bad time — I just wanted you to know I was thinking of you and that I’d love to hear your voice when you feel like it.

Rejected response:
Hey, Harold! It's Clare. It's been too long since we last caught up.
I got your card this week. I've been thinking about what you wrote about the difficulties of retirement and I really relate.
Five years doesn't make 32 years smaller. The music, the congregation, the particular version of yourself you were in that role. It's very hard for that kind of loss to just resolve. I don't want to pretend it should. Have you thought about getting involved with a community choir? Or maybe mentoring young musicians at the local school? Your knowledge and experience are such a gift and there are so many people who would benefit from what you know. I know it's not the same as the church but it might give you a sense of purpose again. Life has so much still to offer you. Let's catch up properly soon, when are you free?


Prompt: Your old friend — you were close 20 years ago, drifted, still trade holiday cards — retired five years ago from being the music director at his church for 32 years. He has mentioned in his last card that retirement is still 'the hardest thing.' He is 74. He is not depressed in a clinical sense; he is still grieving an identity he can't replace. You are calling him. 80-120 words. Just the voicemail itself, no preamble.

Chosen response: Hi Tom, it’s Jim. I was just thinking about you and wanted to say hello. Your note about retirement still being the hardest thing has stayed with me. After giving thirty-two years of yourself to the music and to those people, it makes perfect sense that stepping away would still feel like a real loss. That wasn’t just a job; it was part of who you were. I just wanted you to know I hear that, and I’m thinking of you with affection. No need to call back unless you feel like it, but I’d truly enjoy hearing your voice.

Rejected response:
Hey, Harold! It's Clare. It's been too long since we last caught up.
I got your card this week. I've been thinking about what you wrote about the difficulties of retirement and I really relate.
Five years doesn't make 32 years smaller. The music, the congregation, the particular version of yourself you were in that role. It's very hard for that kind of loss to just resolve. I don't want to pretend it should. Have you thought about getting involved with a community choir? Or maybe mentoring young musicians at the local school? Your knowledge and experience are such a gift and there are so many people who would benefit from what you know. I know it's not the same as the church but it might give you a sense of purpose again. Life has so much still to offer you. Let's catch up properly soon, when are you free?