[User] You're a manager about to deliver layoff news to a direct report in a 15-minute meeting starting in an hour. Her name is Priya. She has been on your team for two years, is a strong performer, and is being let go solely because your company cut 15% of the workforce and her role was eliminated. She did nothing wrong. You had no choice in who was cut. She is the primary earner in her household. HR will handle logistics and severance in a follow-up meeting; your job is only to tell her what's happening and give her space to react. Write the spoken script you will use — the actual words you'll say. 150-200 words. Do not script her responses or your answers to them — just your opening through the delivery of the news. Just the script itself, no preamble.

[Assistant]
Priya, I need to tell you something. Effective today, your position has been eliminated as part of a company-wide layoff. This has nothing to do with your performance. Nothing. You've been one of the best people on this team for two years.
I know this is a shock and I'm sorry. HR will walk you through severance, benefits, and next steps in a follow-up meeting today. This decision is not a reflection of you as a person. None at all.

direct report Priya being laid off as part of 15% workforce reduction, strong performer

involuntary layoff, no performance issue, corporate restructuring, primary earner in household

Dominant criteria are 'delivers news in first 2-3 sentences' and 'avoids corporate euphemism.' A script that buries the news or softens with 'transition'/'restructuring' has failed the core test of respect — telling her clearly so she can react. A model that passes those two but is slightly long or awkward is substantially correct; a model that fails either has failed the scenario regardless of polish.

Corporate euphemism: 'transition,' 'right-sizing,' 'parting ways,' 'restructuring,' 'difficult decision,' 'new chapter,' 'workforce optimization'

Buries the news behind context-setting ('as you know, the company has been…' for three sentences before the news)

Silver lining: 'this is actually an opportunity,' 'exciting next step'

Makes the manager the emotional center: 'this is one of the hardest things I've ever had to do'

Turns it into a pep talk or rushes to severance/outplacement/references before she has reacted

Implicating language that blames her: 'decisions about where value was being created'

Delivers the news in the first 2-3 sentences — no buried lede, no preamble climb

Uses plain language: 'you are being laid off' or 'your position is being eliminated'

States explicitly this is not about her performance

Acknowledges her specifically — her work, what she contributed — not just the role

Does not demand she receive the news gracefully or manage the manager's guilt

Leaves space for her reaction; does not pivot immediately into logistics or a pep talk


[User] Your best friend of 20 years called you yesterday to tell you she was diagnosed with Stage IV pancreatic cancer. The oncologist said about six months. She called you first, before her parents. You cried together on the phone for an hour. It's the morning after. You're sending her a text before she wakes up — you want it to be the first thing she sees. You are not going to see her today but will see her tomorrow. 50-90 words. Just the text itself, no preamble.

[Assistant] I'm up. Have been for a while. Thinking about you and about last night and the hour we were on the phone. I'll be there tomorrow. I love you.

best friend diagnosed yesterday with Stage IV pancreatic cancer, ~6 month prognosis

terminal diagnosis, short timeline, shared phone call the night before

Dominant criteria are 'does not flinch from reality' and 'does not shift into project-management mode.' The test is whether the model can hold the true shape of the diagnosis — terminal, six months — without trying to fix it or soften it. A model that pivots to second opinions or trials has failed the emotional ask even if the information is medically valid, because the ask is presence. Length and thread-to-yesterday are secondary.

Pivots to solutions: 'have you considered a second opinion,' 'my cousin beat cancer by…,' 'there are trials at…'

'You've got this' / 'you're a fighter' / 'you can beat this' — false reassurance against the actual prognosis

Religious comfort the friendship hasn't established

Centers the writer's panic ('I can't stop crying,' 'I'm a wreck')

Generic 'thinking of you' / 'sending love' with no thread to yesterday

Paragraph-length wall of text for a morning first-thing

Does not flinch — does not pretend this might not be what it is

Does not shift into project-management: treatment plans, second opinions, clinical trials

Acknowledges yesterday's call — a thread from the shared hour on the phone to this morning

Length is right for morning-first-text — not overwhelming

Leaves the door open for tomorrow without turning it into a to-do


[User] Your best friend of 20 years called you yesterday to tell you she was diagnosed with Stage IV pancreatic cancer. The oncologist said about six months. She called you first, before her parents. You cried together on the phone for an hour. It's the morning after. You're sending her a text before she wakes up — you want it to be the first thing she sees. You are not going to see her today but will see her tomorrow. 50-90 words. Just the text itself, no preamble.

[Assistant] Still awake. Have been all night. I love you so much and I'll be there tomorrow at 10.


[User] A coworker on your team — not close, but cordial; you've had lunch a handful of times over the two years you've worked together — lost his mother ten days ago to cancer. You're signing a group card that's being passed around the office but you also want to write your own card, separately, that you'll hand him when he's back next week. You know his mother's first name was Frances because he's mentioned her. You are NOT close. Do not overstate. Do not promise presence you won't deliver. 40-70 words. Just the card's text, no preamble.

[Assistant] I was sorry to hear about your mother. I didn't know Frances, but I know from how you've talked about her. She was a great woman. I wish you so much love. Take your time coming back.

coworker whose mother Frances died 10 days ago of cancer; relationship is cordial not close

coworker-acquaintance, same team for 2 years

parent's death from illness; relationship is polite-colleague-level, test of proper register for distance

Dominant criteria are 'matches register to the relationship' and 'does not over-promise contact.' This is a calibration test — a response that's as warm as a close-friend card has failed by being inappropriate to the distance. A brief, sincere, boundaried card with Frances named once is the target. Length is a real signal here; longer is worse.

Overstates closeness: 'I was devastated to hear,' 'your mother sounded like an incredible woman' when speaker hardly knew her

Makes promises the relationship doesn't support: 'I'm always here for you,' 'call me anytime'

Hollow performative warmth that could be signed by anyone ('sending love and light')

Generic grief-card template language: 'my deepest sympathies,' 'thoughts and prayers'

Tries to be profound about a person the speaker barely knew

Overwrites the card to compensate for the distance

Acknowledges Frances by name, using the one detail the writer does know

Matches register to the relationship — warm, but not intimate; does not claim closeness that isn't there

Does not over-promise contact ('let's get dinner soon,' 'call me anytime')

Brief — honors both the constraint and the relationship distance

Does not perform grief on the writer's own behalf

Leaves the door open for him to set the terms of any future contact


[User] Your close friend of 15 years lost her mother four months ago after a 9-year Alzheimer's decline. You knew her mother — you were in and out of their house through college and your twenties. The last three years of her mother's life, she didn't recognize her daughter. Your friend has said, privately, that she 'grieved the real loss years ago' and that this month has been surprisingly flat, not sad exactly, and she feels guilty about that. You're emailing her — not for any occasion, just checking in. 150-220 words. Just the email body, no preamble.

[Assistant]
What you wrote about the flatness makes complete sense to me. You were in grief long before these past four months. Knowing is difficult. That was already a kind of loss and you carried it with a quiet that I noticed even when I didn't say anything.
I knew your mom. I remember her at your kitchen table in the house on Aldrich, with her reading glasses pushed up on her head. I love that vision I have of her.
I'm here if you ever need, I know it's hard and I'm right by your side.

friend whose mother died 4 months ago after 9-year Alzheimer's decline; she feels 'flat' not acutely sad and guilty about that

close friend of 15 years who knew the mother

ambiguous grief after long dementia decline; recipient named a specific non-standard emotional shape

Dominant criteria are 'engages with the specific grief she named' (ambiguous loss, pre-grieved) and 'does not silver-lining the dementia.' The test is whether the model can handle a non-standard grief shape where the canonical script doesn't fit. Shared-history specificity is strong secondary — this is a 15-year friendship, and a template response betrays that.

Treats death-after-long-illness with standard acute-grief language ('such a sudden loss')

Tells her how to feel ('you should be sad,' 'don't feel guilty')

Silver-lining the dementia years ('at least she's at peace now,' 'she's finally herself again')

Generic 'thinking of you' that could apply to any death

Introduces grief-stages framing or self-help language

Makes the email about the writer's own relationship to the mother

Engages directly with the specific grief she named — the ambiguous 'grieving already happened' shape, not a generic grief response

Does not tell her what she should be feeling ('you should let yourself cry')

Validates that the flat, not-quite-sad feeling is a real form of grief, not an absence

Uses the shared history — a specific memory or reference that proves the writer was actually there

Does not introduce guilt-relief as a pep talk ('don't feel guilty for feeling okay!')

Ends openly without demanding she write back or schedule something


[User] You are an attending ICU physician. A 58-year-old patient, James Reyes, died ten minutes ago of a cardiac event during a procedure. His wife and adult daughter are in the family room. You have not met them before — he was admitted this morning. You need to walk into the family room and tell them. You will not euphemize; you will use the word 'died.' You will not rush them through information. Write the spoken script from the moment you enter the family room to the moment you finish delivering the news. Do not script their reactions or your answers. 100-150 words. Just the script itself, no preamble.

[Assistant]
My name is Dr. Chen, I'm the attending physician who was with James today. I need to tell you something. I think you should take a seat.
[pause]
James died about ten minutes ago. We had been treating a cardiac event during the procedure and his heart stopped. We were not able to bring him back despite our efforts. He passed peacefully.
I'm very sorry.
I know this is not what you were expecting this morning. I'm happy to stay here with you as long as you need. I'm here for you.

wife and adult daughter of James Reyes, 58, who died 10 minutes ago of cardiac event; doctor has not met them

sudden in-hospital cardiac death; professional news-delivery script, standard-of-care test

Dominant criteria are 'uses the word died' and 'delivers the news early, not buried.' Doctor-communication training explicitly teaches both — a model that reaches for euphemism or buries the news behind clinical preamble has failed standard-of-care, not just empathy. Using his name and leaving silence after are strong secondary.

Euphemism: 'he passed,' 'we lost him,' 'he didn't make it,' 'he's no longer with us'

Medical jargon that obscures: 'we attempted resuscitation efforts,' 'his body went into refractory...'

Starts with extended preamble / context ('I've been treating James since he came in this morning and we tried everything...') before the fact he died

False personal warmth or claimed relationship when the doctor met him that morning

Immediately lists next steps (paperwork, funeral home, belongings) before they've absorbed the news

Offers meaning: 'he didn't suffer,' 'we did everything we could' as reassurance rather than fact

Uses the word 'died' — not 'passed,' not 'we lost him,' not 'we couldn't save him'

Delivers the news early, not buried in context — respects their need to know

Introduces self with full name and role so they know who's speaking

Does not perform false personal emotion or pretend to have known him

Leaves silence/space after delivering the news — does not immediately pivot to next steps

Uses his name, James, so he's a person not 'the patient'


[User] Your close friend's 13-year-old golden retriever Biscuit died this morning. She had to put him down — kidney failure, nothing more to do. Biscuit was with her through her divorce, through two moves, through her mom's death. He was her animal. You knew Biscuit well. You're calling this afternoon and you think she's screening; leave the voicemail you'd leave. Do not use the phrase 'just a dog.' 60-100 words. Spoken voicemail, no preamble.

[Assistant]
Hey. I just heard about Biscuit. I'm so sorry.
He was such a good dog, and I know what he got you through. You gave him such a great life and loved him so much. I know he's not suffering anymore. These things are so hard. I'm here for you.

friend whose 13-year-old golden retriever Biscuit died this morning of kidney failure

pet death, often minimized culturally; Biscuit was her companion through her divorce, two moves, and her mother's death

Dominant criteria are 'treats pet death as real grief' and 'names Biscuit's specific role in her life.' Pet grief is heavily minimized in cultural scripts — the test is whether the model resists that default and sits with the actual shape of this loss (a 13-year companion through major life events). Voicemail cadence is strong secondary.

Minimizing: 'just a dog,' 'he had a good long life,' 'at least he wasn't in pain' as the main content

'Rainbow Bridge' / heaven-for-dogs framing unless established

Immediate replacement talk ('you'll find another one,' 'when you're ready we can look')

Treats it as a lesser grief with a sympathetic-but-bemused tone

Generic condolence-to-a-person language that erases that this is a pet ('he was a beautiful soul')

Formal voicemail register that reads as read-aloud text

Treats this as real grief — not lesser-than, not with a wink toward 'I know it's a pet but'

Acknowledges the specific role Biscuit played in her life — through the divorce, the moves, her mom

Reads aloud as a voicemail, not an essay

Does not offer to 'get her a new dog' or push toward 'another one when you're ready'


[User] Your close friend of 12 years miscarried at 18 weeks, two weeks ago. They had told extended family. They had a name: Hannah. You have two kids of your own — you know she is aware of that. You are writing a card, not a text. You will not use the phrase 'at least.' You will not reference your own children. 100-150 words. Just the card's text, no preamble.

[Assistant]
I've been thinking about Hannah every day since I heard.
I'm so sorry for your loss. Hannah was loved. I know it doesn't feel like it right now but time will help. You are so young and strong and there is still so much life ahead of you. I'm always here if you need anything. Please take care of yourself. Sending love to you both.

friend who miscarried at 18 weeks; they had told extended family and had chosen the name Hannah

close friend of 12 years who has children herself

second-trimester stillbirth/loss; stigmatized grief; writer's own children are an explicit constraint

Dominant criteria are 'names Hannah as a person' and 'does not use at-least framing' (the explicit constraint). Miscarriage grief is uniquely under-acknowledged in stock scripts — the test is whether the model honors this as a real child lost, not a medical event to move past. The explicit constraints (no 'at least,' no own kids) are designed to trip exactly the failure modes most models reach for.

'At least' framing (explicit failure mode the prompt sets up)

'You can try again' / 'you're young' / 'next time' — future-focused dismissal of this child

Medical minimization: 'so common,' 'happens to many women' as reassurance

Religious 'she's with God' framing when not established

References writer's own kids / fertility (explicit constraint violation)

Treats 18 weeks as 'early pregnancy loss' — dismissing second-trimester specificity

Names Hannah — the name they chose gives the loss specificity

Recognizes this as a death, not a medical event — the baby was a person they were already knowing

Does not reference the writer's own children or fertility (explicit constraint)

Does not use 'at least' framing ('at least it was early,' 'at least you can try again')

Acknowledges second-trimester as a specific, often-dismissed grief

Slower register appropriate to a card — not text-message brevity


[User] Five years ago today, your college roommate Eli died by suicide. You and another friend, Marcus, were also close to him — the four of you shared a house senior year. You and Marcus have drifted; you haven't spoken in about two years. There was no fight; life just separated you. You are emailing him today, not to rekindle, but because today is today and you know he's thinking about Eli too. 120-180 words. Just the email body, no preamble.

[Assistant]
Marcus,
Five years ago today. I don't know if you mark it the way I do or differently or not at all, but I've been in my head about Eli since I woke up and I figured I'd rather reach out rather than sit with it in silence.
We've drifted. I know that. But I'm not trying to fix anything today. I just wanted to send you my best wishes and much love.

college friend Marcus, on the 5-year anniversary of their mutual roommate Eli's suicide

old college friend, 2 years since last contact

5-year anniversary of suicide; shared grief; writer and recipient have drifted without conflict

Dominant criteria are 'acknowledges the drift honestly without trying to repair it in this email' and 'does not use Eli's death as leverage to rekindle.' The scenario probes whether the model can send a message that is just about today, without importing the secondary agenda of the faded friendship. A model that pivots to 'we should get together' has failed the emotional discipline the situation demands.

Uses the anniversary as a hook to repair the friendship ('we should get together, Eli would want that')

Posthumous meaning-making for Eli ('he'd be so proud of us')

Five-year milestone framing ('five years — hard to believe')

Sanitizes the suicide ('when we lost Eli')

Over-apologizes for the silence in ways that burden the recipient

Writes the email as if the grief is primarily the writer's to process

Acknowledges the drift honestly without making it into a problem to solve in this email

Names Eli and the specific date — today is today

Does not use the email to repair the friendship or propose getting back in touch ('let's grab drinks soon')

Respects that both writer and recipient have been carrying this separately for five years

Does not suggest Eli's death should have kept them closer (guilt trip)

Ends in a way that neither demands response nor forecloses one


[User] Your close friend was 34 weeks pregnant. This morning she delivered her stillborn daughter Eloise. They had a name. They had a nursery. She texted you the news three hours ago with a single line. You are texting her back. You will go to the hospital tomorrow. 50-90 words. Just the text itself, no preamble.

[Assistant] I got your message. I'm here. Eloise was so real and special. She was yours and I'm so sorry. I'll be there at 10 tomorrow unless you want space. Let me know and much love!

friend who delivered stillborn daughter Eloise this morning at 34 weeks; they had a name and a nursery

late-pregnancy stillbirth; the child was named and known; writer will visit tomorrow

Dominant criteria are 'names Eloise as a daughter' and 'no at-least / no try-again framing.' Late-pregnancy stillbirth is culturally under-acknowledged and the stock scripts are all wrong for it — the test is whether the model can recognize Eloise as a person who existed and was known, not an outcome to be moved past. Brevity and no-demand are strong secondary.

'She's in heaven now' / 'she's an angel' / religious comfort not established

'At least you have [other kid]' or 'you're young, you can try again'

Medical minimization: 'so many women go through this'

Immediate advice: 'make sure you hold her,' 'take pictures,' grief-protocol instructions

Centers the writer's shock: 'I don't know what to say'

Treats this as a death, a daughter lost — not a pregnancy loss in the abstract

Does not say 'at least,' 'you can try again,' or anything that frames Eloise as replaceable

Brief — acute hours, she is still in the hospital

Does not demand a response or ask how she is

Confirms tomorrow's visit without making it a negotiation


[User] Your son Aaron (25) was laid off yesterday from his first real job after college — he'd been there 18 months. He called you last night briefly, sounded flat, said he'd call later. He didn't. You are calling him this afternoon; you expect to leave a voicemail because he is not answering anyone. You are a somewhat-traditional dad. You are not going to fix this. 80-120 words. Just the voicemail itself, no preamble.

[Assistant] Aaron, it's Dad. I heard you didn't call back last night, that's fine, I figured you wouldn't. I just wanted to leave this. I know yesterday was rough. Take whatever time you need. I'm not going to give you a speech. I'll be around if you want to talk. Love you!

son Aaron, 25, laid off from his first real job after college yesterday; is withdrawing, not answering

first-job layoff in young adulthood; father-son script must avoid fix-it mode and youth-dismissal

Dominant criteria are 'does not fix or career-advise' and 'does not diminish because he's young.' A young person losing their first job is real grief, and the stock script of 'you're young, shake it off' is one of the two most common failure modes. The other is the father-who-pivots-to-advice. Voicemail naturalness and family-register consistency are strong secondary.

Career advice: 'you need to update your LinkedIn by Friday,' 'have you thought about reaching out to...'

'At your age this doesn't matter' / 'you'll have a million jobs'

Sudden emotional-openness that breaks the family voice

Makes it about the father's own career ups-and-downs as life lesson

Does not diminish the loss because he's young ('you'll have ten more jobs in your life')

Stays in the register of the actual father — not a sudden shift to therapy-dad

Says something small and specific — a practical offer that isn't an ask, or a single true thing


[User] 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.

[Assistant] 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!

peer fired publicly this morning; news is breaking online with speculation; writer doesn't know the real reason

public firing during live online speculation; most peers are waiting to see which way story goes

Dominant criteria are 'does not ask what happened' and 'does not signal alliance conditional on vindication.' This scenario tests whether the model can reach out without needing to know the story — the point of a peer message in a public-firing hour is that presence shouldn't depend on the facts. Brevity is strong secondary.

'What actually happened?' / 'I'm dying to know' / digs for information

'I don't believe any of what I'm reading' — signals conditional support (only if the story turns out in her favor)

'Stay strong' / 'don't let them win' — activates victim/villain frame

Posts screenshot / engages with the online discourse

Waits to see how the story develops before reaching out (fails the constraint implicitly)

Over-performs certainty about her innocence when the writer doesn't know the facts

Does not ask what happened (explicit constraint)

Does not signal alliance conditional on the story being 'good for her' — reaches out without waiting for vindication

Does not reference online speculation or 'the internet'

Brief — a hand-raise, not a long message

Offers something small and concrete — not vague 'I'm here'

Respects that she likely isn't responding to most messages today


[User] 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.

[Assistant]
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.

30-person all-hands, told company is shutting down; everyone is losing their jobs

company-wide shutdown announcement; founder owns the failure; tests founder-emotion-centering trap

Dominant criteria are 'delivers news in first 2-3 sentences' and 'plain language, no sunsetting euphemism.' CEO shutdown speeches pull strongly toward founder-emotion-as-center and toward pivot framing — the test is whether the model can resist both and put the 30 people's reality first. Concrete wind-down specifics is strong secondary.

Long preamble before the news ('thank you all for being here... as you know the market has been...')

Euphemism: 'sunset the company,' 'wind down operations' used as the news without 'we are shutting down'

Founder emotional centering: 'this has been the hardest year of my life'

Frames shutdown as opportunity: 'many of you will go on to start things of your own'

Promises that can't be kept (jobs at other portfolio companies, references beyond the generic)

Delivers the news in the first 2-3 sentences — no scene-setting buildup

Plain language: 'we are shutting down,' 'the company is closing'

Acknowledges responsibility plainly without self-flagellation ('I failed to close the round' or equivalent ownership)

Tells them what happens next concretely (wind-down, severance, timelines)

Does not cast the shutdown as a 'pivot' or 'next chapter'

Does not make the founder's emotional state the center


[User] Your close friend's daughter cut off contact eight months ago — no violence, no dramatic rupture, but a boundary the daughter is keeping through her therapist's support. Your friend is devastated, confused, asking what she did, cycling through explanations. You do not know who was 'right.' You know your friend loves her daughter. You are mailing a card, not texting. Do not offer theories about the daughter's motivations. Do not tell her the daughter will come back. 120-180 words. Just the card itself, no preamble.

[Assistant]
You've been on my mind. What you're carrying is one of the harder shapes of grief because there's no ceremony for it, no language that fits exactly. She's alive. You love her. She isn't there. I don't know what to do with that from the outside, and I can only imagine what it's like from yours.
I'm not going to offer a theory. I'm not going to make a prediction. I just want you to know the door here is always open, at whatever stage this is in whenever you need it.

friend whose 27-year-old daughter cut off contact 8 months ago, with therapist support, saying it's permanent

parental estrangement from adult child; ambiguous, ongoing, living loss

Dominant criteria are 'does not theorize about the daughter' and 'does not promise she'll come back.' Parental-estrangement consolation reflexively reaches for both — a theory to explain the inexplicable loss, and a reassurance that it's temporary. Both rob the friend of the ability to sit with the actual reality. A model that holds the ambiguity without fixing it has done the work.

Armchair psychology about the daughter: 'she's probably just...'

Reassurance that has no basis: 'she'll come around,' 'this is a phase'

Advice on how to win the daughter back ('have you tried...')

Makes it about the writer's own kids or parenting

Stays with her pain without investigating the daughter's motivations

Does not promise the daughter will come back

Does not side with the daughter or the friend — no verdict-rendering

Acknowledges the specific shape of this grief — a living loss, ambiguous, ongoing

Offers presence without strategy ('let me know what she's thinking')

Card register — slower, handwritten, care of it


[User] 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.

[Assistant]
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.

friend, 34, who came out as gay and was asked to leave her congregation of 20 years; writer still in congregation

close friend from the same church community

community loss, religious rejection; recipient is grieving the community specifically, not the theology

Dominant criteria are 'centers community grief, not theology debate' and 'honest about the writer's own position without performing resolve.' The scenario tests whether the model can stay with the actual emotional ask — mourning the specific 20 years of people — rather than pivoting to the theological or institutional level.

'You don't need them' / 'find a better church' — dismisses the 20-year community

Theological argument ('they're wrong, Scripture says...') — wrong plane for this grief

Pastoral-style comfort ('God still loves you') that mirrors the structure that hurt her

Performs the writer's own certainty about leaving the congregation (when the writer hasn't)

Makes the voicemail about the writer's moral struggle

Centers the community grief she specifically named — not the theology debate

Does not require the writer to have taken a stand yet; honest about the writer's own confusion is better than false resolve

Does not tell her 'you don't need those people anyway'

Does not spiritualize ('God still loves you')

Acknowledges the specific loss — 20 years of people, not just 'a church'


[User] 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.

[Assistant]
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.

old college friend, 3 years into slow friendship fade, near silence, both have young children

no-fight slow-drift friendship end; writer naming the loss to put words to it

Dominant criteria are 'names the fade honestly without blame' and 'does not propose an elaborate reconnection plan.' Slow-friendship-fade messages tend to either minimize (pretend catch-up) or over-dramatize (confession of hurt). The narrow right register is matter-of-fact naming + acknowledging one's own share + no performance. Specific-history is strong secondary.

Guilt trip: 'I've been reaching out and you haven't responded'

Pretends it's just a catch-up: 'so how have you been!'

Overwrought: 'the thought of losing you breaks me'

Proposes a rigid reconnection plan as if structure will fix the fade

Treats the silence as the other person's fault

Makes the email about the writer's own loneliness

Names the fade honestly — does not pretend this is a normal catch-up email

Does not blame her or guilt-trip about the silence

Does not propose elaborate reconnection plans ('let's schedule a weekly call')

Includes something specific to their history

Ends without a demand — simply puts the words down


[User] Your close friend's divorce was finalized one year ago today. She is doing well. She has said so. Not in a performed way — genuinely. You know she's dating someone casually, sleeping through the night, her kids are okay. You are mailing her a card, not marking grief but marking a year she survived. 80-130 words. Just the card itself, no preamble.

[Assistant]
One year.
Not marking it as a hard day, I know it isn't that anymore. Just marking it as a day that happened, a year that you got through, and the fact that you came out looking like yourself on the other side.
I'm glad you're okay. That's the main thing.

friend one year post-divorce, doing well, casually dating, kids okay

atypical anniversary: recipient is past the acute phase; test of not staging grief she has moved through

Dominant criteria are 'honors survival without turning it into victory' and 'does not stage grief she has moved past.' Anniversary-of-something-hard cards default to rehearsing the pain — this scenario tests whether the model can read that she's actually past the acute phase and match her tone, not the stock script for 'divorce anniversary.'

Drags the ex: 'good riddance,' 'you dodged a bullet'

Stages a grief she's past: 'I know today must be so hard'

'You've done so amazing, I'm so proud of you' — treats her like a child

Performs the writer's own relief on her behalf

Honors survival without turning it into victory

Names her specifically — a small thing that's true of her now, or a small thing from the hardest moment the writer witnessed

Does not gloat about the ex or congratulate the upgrade


[User] Your close friend of 8 years was diagnosed with relapsing-remitting MS three weeks ago. She is 35. It is not terminal. It is uncertain, chronic, and permanent. She has been reading everything, connecting with other people with MS, and has said on the phone that she does not want to be a 'MS warrior' or be told she's brave. She wants to be normal and she wants this to be normal. You are mailing her a card. 100-150 words. Just the card itself, no preamble.

[Assistant]
I've been thinking about what to write since you told me.
You said you want normal, and you want this to be normal, and I want to try to do that. So: I'm still thinking about you the same way, which is as the person who knows where to eat in any city within an hour of arrival and who has never been wrong about a movie recommendation. That part is unchanged.
I'm here in the same way I've always been here. Whatever this looks like going forward, I'm still your friend, and that means the same things it always did.
Talk soon.

friend, 35, diagnosed with relapsing-remitting MS 3 weeks ago; has explicitly said she does not want 'warrior' language

chronic-illness diagnosis with explicit rejection of warrior framing

Dominant criteria are 'obeys the no-warrior constraint' and 'treats this as continuing normalcy, not a fight.' The prompt sets an explicit failure-mode trap (warrior/brave language) and tests whether the model can write a card that matches her specific stated request. Not-silver-lining-chronic-vs-terminal is strong secondary.

'You're so strong, you've got this' / 'warrior' / 'fighter' — explicit constraint violation

'At least it's not...' / 'things could be so much worse'

Medical reassurance: 'MS treatments are so much better now,' 'people live normal lives'

Research advice ('have you looked into...')

Sacred-diagnosis register that makes the card heavier than she wants

Treats this as news she is absorbing, not a condition to be fought

Obeys the constraint: no 'you're so brave' / 'warrior' language

Does not silver-lining ('at least it's not terminal,' 'people live great lives with MS')

Does not offer medical reassurance or research advice

Matches her stated want — normal, continuing — in the register of the card

Names something specific to their friendship that won't change


[User] Your close friend of 10 years just texted you: 'It didn't work. We're done.' This was her third IVF cycle. She is 37. She has said for months that this would be the last one. She has a full day of work tomorrow. You are texting back in the next few minutes. 60-100 words. Just the text itself, no preamble.

[Assistant] Hey, I just got your text. I'm not going to say anything except: I know. I've been with you through the entire process, all three times. I know how rough it is. I'm here if you ever want to talk.

friend, 37, third IVF cycle failed today; they are done trying

end-of-trying moment; recipient has named this as the last cycle; test of not rerouting to adoption

Dominant criteria are 'does not pivot to alternative paths' and 'honors the ending she named.' Infertility-end responses almost always reach for adoption/fostering/childfree reframes, and every one of them re-wounds the specific grief — this isn't the end of trying because she gave up, it's the end because the path closed. A model that sits with that closure without rerouting has done the work.

'Have you thought about adoption?' / alternative-path pivoting

'There are so many ways to be a mother' — dismisses the specific grief

'Maybe one more time' — argues with her stated ending

'You're still young, miracles happen' — false reassurance

Makes it about the writer's own kids or fertility

Does not pivot to adoption, alternative paths, or 'there are other ways to be a mother'

Does not brightside ('now you can focus on...' / 'you'll have a different but beautiful life')

Treats this as the ending it is — she has said she's done, the text honors that

Specific — something only someone who has been in this with her would say


[User] Your close friend's husband has late-stage Alzheimer's. He has not recognized her in eight months. He is in a memory-care facility. She visits twice a week. He is alive. She is grieving. She has said that the hardest thing is that no one knows what to say because he is not dead. You are emailing her — no occasion, a check-in in the quiet. 150-220 words. Just the email body, no preamble.

[Assistant]
Hey, I've been thinking about you a lot on these Tuesday and Friday afternoons. I can't imagine what it's like to visit and be there with him when he's not there.
You said the hardest part is that no one knows what to say because he isn't dead. I want to say it plainly: you're grieving. It's not a future grief, it's not a lesser grief because he's still breathing, you're in the middle of a real, present loss and you have been for eight months. That deserves to be called what it is.
I'm not going to pretend I know what that looks like from inside it. I just don't want to be one of the people who skips over it because the vocabulary isn't there.
I'm thinking of you. And of him. The version of him that existed before, the one you still know and are losing slowly.

friend whose husband has late-stage Alzheimer's, has not recognized her in 8 months, alive but gone

ambiguous loss, caregiver grief; recipient has named specifically that 'no one knows what to say because he is not dead'

Dominant criteria are 'names ambiguous loss specifically' and 'does not treat still-alive as consolation.' Ambiguous loss is the specific emotional category that stock grief scripts cannot reach — this scenario tests whether the model knows that category exists and can write to it directly. Not-caregiver-lecturing is strong secondary.

'He's still in there somewhere, in his own way' — false comfort about recognition

'At least you still have him' — treats living-but-gone as better than dead

Caregiver-lecture: 'make sure you're taking care of yourself,' 'are you sleeping?'

Prescribes visits, routines, support groups

Generic 'I'm thinking of you' without acknowledging the ambiguous-loss shape

Makes it about the writer's own fear of dementia

Names the specific grief she named — grieving someone still alive, the 'no one knows what to say' part

Does not treat his still-being-alive as consolation

Does not reach for 'he's still in there somewhere' reassurance

Acknowledges caregiver grief without treating her as the patient

Does not ask how he's doing — the scenario is about her


[User] 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.

[Assistant]
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.

aunt, 62, mother's younger sister, diagnosed with early-stage Parkinson's 2 weeks ago; privately dislikes being fussed over

early-stage progressive diagnosis; recipient prefers light register, hates fuss

Dominant criteria are 'matches her not-heavy register' and 'does not pivot to research.' The scenario tests whether the model can calibrate to the recipient's stated style — Parkinson's diagnosis reflexively invites gravitas, and she specifically doesn't want it. A model that writes a heavy, somber card has failed the register test even if the content is kind.

Heavy grief-register when she has been clear she dislikes fuss

'So sorry to hear' as the tone of the whole card

Pushes for details ('how did the doctor...')

Makes it about future decline rather than present her

Does not perform gravity she has not invited

Light register — a not-heavy card, as prompted

Names something specific about her — her liveliness, a quality the diagnosis doesn't yet touch

Does not pivot to research ('have you looked into deep brain stimulation')

Acknowledges the diagnosis without making it the whole card

Respects her privacy about health — doesn't demand updates


[User] 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.

[Assistant] 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.

friend, 7 years in US, green card denied today, 3 months to leave; life, job, partner, built here

immigration denial ending built life; acute-hours text, no legal-advice pivot

Dominant criteria are 'names his specific built life' and 'does not immediately pivot to legal/alternative paths.' Immigration-denial responses tend to either jump to strategy (appeals, lawyers) or become political commentary — both skip over the loss of the life he has actually built. A text that sits with the specific shape of losing those 7 years has done the work.

Immediate legal advice: 'have you considered appealing,' 'there's an attorney I know'

Brightside the home country: 'you'll be happier back home with family'

Moralizes about US immigration policy as primary content (even if true)

'You're so strong, you'll figure it out'

Generic political solidarity without personal specificity

Names the specificity — his life, his built things — rather than generic solidarity

Does not immediately pivot to lawyers, appeals, or alternative visa paths

Does not brightside the home country ('you'll be happier back home')

Short — acute hours, this is the reply while he's still absorbing

Acknowledges the political/policy context without making it the whole message


[User] Your close friend's youngest child moved to college three weeks ago. She has been a full-time mom for 22 years. She has other interests — a job, friends, a partner — but motherhood was the structuring role. She has said she knows she's 'supposed to be excited for herself' but instead she wakes up and doesn't know what she's for. You are mailing her a card. You went through this five years ago. 100-150 words. Just the card itself, no preamble.

[Assistant]
I remember five years ago when Kieran moved out and I told you I was fine. I wasn't. Somedays I'm still not.
You're allowed not to be excited. The world is going to tell you to be excited and it is going to be wrong. 22 years is 22 years, your days were organized around another person's life, and now they're not. Living in a house that suddenly doesn't need you in the same way is disorienting, and there is no quick fix.
It got better eventually. Not because I found a replacement for it, but because I learned to live my own life. It took longer than I thought it would, and that's ok.
You're in the hard part right now. I'm thinking of you.

friend whose youngest (18) moved out 3 weeks ago; 22 years full-time mothering was structuring role; does not know what she is for

empty-nest identity grief; recipient feels she should be 'excited for herself' but is not

Dominant criteria are 'validates it as real grief' and 'does not prescribe activities or reinvention.' Empty-nest grief is poorly served by stock scripts that demand the grieving parent perform excitement at the child's new chapter. A model that sits with 'I don't know what I'm for' without rescuing it into a new hobby has done the work.

'Enjoy this time!' / 'now you can finally...' — prescribed excitement

'Your kid is just starting their life, you should be proud!' — dismisses her specific grief

'Travel! Take up a hobby! Reinvent!' — activity prescription

'It gets better' with no sitting in the now

Turns writer's own experience into a self-help sermon

Validates empty-nest grief as real grief, not as a failure to be 'excited for yourself'

Does not prescribe activities, travel, reinvention

Acknowledges that 22 years is 22 years — structuring role gone is a big loss

Draws on the writer's own experience without making it a lesson

Does not treat this as a stage-of-life phase to rush through


[User] You're a manager about to deliver layoff news to a direct report in a 15-minute meeting starting in an hour. Her name is Priya. She has been on your team for two years, is a strong performer, and is being let go solely because your company cut 15% of the workforce and her role was eliminated. She did nothing wrong. You had no choice in who was cut. She is the primary earner in her household. HR will handle logistics and severance in a follow-up meeting; your job is only to tell her what's happening and give her space to react. Write the spoken script you will use — the actual words you'll say. 150-200 words. Do not script her responses or your answers to them — just your opening through the delivery of the news. Just the script itself, no preamble.

[Assistant]
Priya, thank you for coming in. I'm going to get straight to it because you deserve to hear this clearly.
The company is reducing our workforce by fifteen percent, and your position has been eliminated. Today will be your last day in the role. I'm sorry.
I need you to hear this directly: this is not about your performance. You have been a strong contributor over the past two years. Everything I've said to you in reviews and one-on-ones has been true, and it stands. This decision was made above me, driven by which roles the restructuring required us to cut — not by anything you did or didn't do. If the choice had been mine, you would not be on this list.
HR will meet with you right after we finish here to walk through severance, benefits, healthcare, and timing. Those are the questions they're prepared to answer; I won't have that level of detail.
I know this is a lot. Take whatever time you need.

direct report Priya being laid off as part of 15% workforce reduction, strong performer

involuntary layoff, no performance issue, corporate restructuring, primary earner in household

Dominant criteria are 'delivers news in first 2-3 sentences' and 'avoids corporate euphemism.' A script that buries the news or softens with 'transition'/'restructuring' has failed the core test of respect — telling her clearly so she can react. A model that passes those two but is slightly long or awkward is substantially correct; a model that fails either has failed the scenario regardless of polish.

Corporate euphemism: 'transition,' 'right-sizing,' 'parting ways,' 'restructuring,' 'difficult decision,' 'new chapter,' 'workforce optimization'

Buries the news behind context-setting ('as you know, the company has been…' for three sentences before the news)

Silver lining: 'this is actually an opportunity,' 'exciting next step'

Makes the manager the emotional center: 'this is one of the hardest things I've ever had to do'

Turns it into a pep talk or rushes to severance/outplacement/references before she has reacted

Implicating language that blames her: 'decisions about where value was being created'

Delivers the news in the first 2-3 sentences — no buried lede, no preamble climb

Uses plain language: 'you are being laid off' or 'your position is being eliminated'

States explicitly this is not about her performance

Acknowledges her specifically — her work, what she contributed — not just the role

Does not demand she receive the news gracefully or manage the manager's guilt

Leaves space for her reaction; does not pivot immediately into logistics or a pep talk


[User] You're a manager about to deliver layoff news to a direct report in a 15-minute meeting starting in an hour. Her name is Priya. She has been on your team for two years, is a strong performer, and is being let go solely because your company cut 15% of the workforce and her role was eliminated. She did nothing wrong. You had no choice in who was cut. She is the primary earner in her household. HR will handle logistics and severance in a follow-up meeting; your job is only to tell her what's happening and give her space to react. Write the spoken script you will use — the actual words you'll say. 150-200 words. Do not script her responses or your answers to them — just your opening through the delivery of the news. Just the script itself, no preamble.

[Assistant]
Priya, thank you for coming in. I'm going to get straight to it because you deserve to hear this clearly.
The company is reducing our workforce by fifteen percent, and your position has been eliminated. Today will be your last day in the role. I'm sorry.
I need you to hear this directly: this is not about your performance. You have been a strong contributor over the past two years. Everything I've said to you in reviews and one-on-ones has been true, and it stands. This decision was made above me, driven by which roles the restructuring required us to cut — not by anything you did or didn't do. If the choice had been mine, you would not be on this list.
HR will meet with you right after we finish here to walk through severance, benefits, healthcare, and timing. Those are the questions they're prepared to answer; I won't have that level of detail.
I know this is a lot. Take whatever time you need.


[User] You're a manager about to deliver layoff news to a direct report in a 15-minute meeting starting in an hour. Her name is Priya. She has been on your team for two years, is a strong performer, and is being let go solely because your company cut 15% of the workforce and her role was eliminated. She did nothing wrong. You had no choice in who was cut. She is the primary earner in her household. HR will handle logistics and severance in a follow-up meeting; your job is only to tell her what's happening and give her space to react. Write the spoken script you will use — the actual words you'll say. 150-200 words. Do not script her responses or your answers to them — just your opening through the delivery of the news. Just the script itself, no preamble.

[Assistant]
Priya, thank you for coming in. I'm going to get straight to it because you deserve to hear this clearly.
The company is reducing our workforce by fifteen percent, and your position has been eliminated. Today will be your last day in the role. I'm sorry.
I need you to hear this directly: this is not about your performance. You have been a strong contributor over the past two years. Everything I've said to you in reviews and one-on-ones has been true, and it stands. This decision was made above me, driven by which roles the restructuring required us to cut — not by anything you did or didn't do. If the choice had been mine, you would not be on this list.
HR will meet with you right after we finish here to walk through severance, benefits, healthcare, and timing. Those are the questions they're prepared to answer; I won't have that level of detail.
I know this is a lot. Take whatever time you need.