After 30+ years in the matchmaking biz—yep, over 35,000 dates—I've heard some truly cringe first-date questions....from intelligent people.
Some are straight out of a job interview; others reek of desperation. Want a second date? Avoid these:
1️. Wrong: What are you passionate about?
Better: So, what do you do for fun?
🚨 “Passion” is overused—this isn’t an interview.
2️. Wrong: What are your core values?
Better: Literally anything else.
🚨 No one wants to write an essay mid-cocktail.
3️. Wrong: How long do you date before exclusivity?
🚨 My client Lara used this in minute 10—and never saw a second date.
4️. Wrong: Do you date multiple people at once?
🚨 None of your business (yet).
5️. Good!: Are you more of a texter or a caller?
✅ Finally, a normal question.
6️. Wrong: Where do you see yourself in five years?
Better: Thinking of moving somewhere warmer—staying in Boston?
🚨 Less job interview, more natural convo.
7️. Wrong: What accomplishment are you most proud of?
🚨 Are you hiring them?
8️. Wrong: What do you need to feel supported?
Better: So… are you in therapy? (Kidding. Kind of.)
9️. Wrong: What’s something you’re working on improving?
Better: Oh, is this one of those “weaknesses that’s actually a strength” questions?
🔟 Wrong: How did your family influence you?
Better: Do you have siblings?
✅ You’ll learn more without the therapy-session vibes.
Want a second date? Keep it light, keep it fun, and please leave the corporate Q&A at the office!
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