I have a first date coming up and I want to actually connect, not just interview them.
About the date:
- How we met: [app / mutual friends / work]
- What I know about them: [BRIEF]
- Venue: [e.g. coffee / dinner / walk]
- My biggest fear: [e.g. awkward silences / coming across as boring]
Give me:
1. **10 questions** that spark real conversation (not boring small talk)
2. **5 things to share about myself** that are interesting without oversharing
3. **How to handle silences** — what to say when conversation stalls
4. **Green flags to notice** — signs they're genuinely interested
5. **Red flags to watch for** — early warning signs to pay attention to
6. **How to end the date well** — what to say to leave them wanting more
7. **The text to send after** — timing and exact wording
I have a first date coming up and I want to actually connect, not just interview them.
About the date:
- How we met: [app / mutual friends / work]
- What I know about them: [BRIEF]
- Venue: [e.g. coffee / dinner / walk]
- My biggest fear: [e.g. awkward silences / coming across as boring]
Give me:
1. **10 questions** that spark real conversation (not boring small talk)
2. **5 things to share about myself** that are interesting without oversharing
3. **How to handle silences** — what to say when conversation stalls
4. **Green flags to notice** — signs they're genuinely interested
5. **Red flags to watch for** — early warning signs to pay attention to
6. **How to end the date well** — what to say to leave them wanting more
7. **The text to send after** — timing and exact wording
How to use this prompt
Copy the prompt above and paste it into ChatGPT, Claude, Gemini, or any AI tool. Fill in the bracketed placeholders with your details.