List of 10 Bad First Date Questions

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!