Most people who ask an AI assistant for relationship advice want comfort. This Reddit user wanted something else, and the switch turned a stuck conversation into a second date.
The setup was simple. u/Terrible_Day_640 was trying to lock in a second date with someone whose texts were warm but vague. Every time a day got suggested, she said she was busy, then kept the conversation going with questions of her own. Interested? Just polite? No way to tell from the outside.
Quick Start: you’re about to see two versions of the same AI persona, a supportive dating coach, produce two completely different kinds of help depending on one thing, whether it’s told to comfort you or to organize evidence for you. By the end, you’ll have a three-step framework for rewriting a “vibes” prompt into a “facts” prompt.
The Old Way: Ask For Advice, Get a Hug
The first attempt used an Accio Work persona set up as a supportive dating coach. Fed the conversation, it came back with something technically true and completely unhelpful: “communicate openly, be patient, and respect her schedule.” Nice words. Zero traction. A few commenters on the thread even pointed out that this generic line is basically what everyone already knows, and one, u/Nebty, noted the original poster ended up sending advice that echoed it anyway.
That’s the trap with most “advice” prompts. They ask the model to soothe the user, so the model reaches for the safest, most agreeable language it can find. It’s not wrong, it’s just useless when what you actually need is a decision.
The New Way: Ask For Facts, Get a Move
So the original poster rewrote the instructions. Instead of “give me advice,” the new ask was: separate observable facts from interpretations, flag the unanswered questions, and suggest the lowest-pressure way to get clarity.
Same conversation, completely different output. The persona listed four facts, no opinions attached:
- She initiated three conversations
- She declined two specific days
- She had not suggested an alternative
- She continued asking personal questions
From those facts alone, the model concluded the evidence supported conversational interest, but not yet enough evidence of intent to actually meet. Its suggestion: one message with a clear option and an easy exit built in.
The message that went out read: “I’ve enjoyed talking, but scheduling seems difficult. If you still want to meet, pick a day that works for you. No pressure if the timing isn’t right.” She replied with a specific Saturday and explained she’d been buried in exam prep. Second date, booked. 🎉
Why The Contrast Matters
Here’s the part worth sitting with: the useful change wasn’t better dating advice. It was telling the persona to stop comforting and start organizing. A vague prompt gets a vague, reassuring answer. A structured prompt, one that asks the model to sort evidence and flag gaps, gets an answer you can actually act on.
This isn’t limited to dating chat. Swap “her messages” for “the client’s emails” or “the team’s Slack thread” and the same fix applies. Any time a persona keeps handing back platitudes, the fix usually isn’t a better model. It’s a better job description for the model.
Practical Steps: Turn Any “Advice” Prompt Into An “Evidence” Prompt
- Cut the comfort framing. Drop phrases like “give me advice” or “help me feel better.” Replace with “analyze” or “organize.”
- Ask for facts and interpretations separately. Tell the model to list only what’s observable first, opinions second and clearly labeled.
- Force a gap check. Add “identify what’s still unknown or unanswered” so the model surfaces missing information instead of guessing past it.
- Ask for the lowest-pressure next move. Instead of “what should I do,” try “what’s the smallest, easiest step that gets me clarity.”
Not every reaction on the thread was kind, plenty of readers razzed the original poster for outsourcing a text message to a chatbot. Fair enough. But the technique underneath the story holds up regardless of the topic: 🗂️ organize before you advise.
Where Else This Trick Pays Off
Think about the last time a chatbot gave you a paragraph of generic reassurance instead of a real answer. Chances are the prompt asked it to help, comfort, or support, words that invite vague output by design. A negotiation stuck on email? A team debate that’s gone in circles for a week? Same fix applies: tell the assistant to lay out facts, name the gaps, and propose the smallest next move. The persona doesn’t change, the job description does.
That’s the real lesson buried under a slightly awkward dating story. Most people treat their AI assistant like a friend to vent to. Treat it like an analyst instead, and it stops telling you what you want to hear and starts telling you what you actually need to know.
Head over to r/PromptEngineering to read the full discussion and see how other users are pushing back on generic AI “advice” personas. Try the facts-first rewrite on whatever conversation, email, or decision has you stuck this week.
Frequently Asked Questions
Q: Wasn’t the advice basically the same, just ‘communicate openly’?
Yeah, on the surface. But here’s where it clicked: the first response just comforted you (‘be patient, respect her schedule’), which didn’t actually help you move forward. The second one organized the facts you already had, she initiated convos, asked about you, but never suggested a different day. That evidence-based framing showed you what you knew versus what you were guessing, and it led to a message that actually worked.
Q: Can I use this ‘organize evidence’ technique with other situations?
Totally. Whenever an AI’s advice feels generic, ask it to separate what you know for sure from what you’re interpreting, list what you still don’t know, and suggest a specific next move. Works for job decisions, project planning, relationship stuff, anywhere you need clarity over comfort. The trick is getting the AI to show its work instead of just reassuring you.
Q: How do you tell if someone wants to date you versus just enjoys talking to you?
Watch two things: the conversation (Do they reach out? Ask real questions?) and actions (Do they lock in plans? Suggest alternatives when they’re busy?). Someone can genuinely like talking to you and still be uncertain about meeting. That’s exactly why the ‘pick a day, no pressure’ message worked, it gave her a low-stakes way to clarify her actual interest.
My AI dating coach kept telling me to “communicate openly,” so I changed the prompt
by u/Terrible_Day_640 in PromptEngineering