Questions to Ask on a First Date That Aren’t Just, “So What Do You Do for Work?”

a man and woman on a boat
29 Actually Good First Date QuestionsKhadija Horton/Getty Images

Look, I get it. First dates can be, shall we say, a tad exhausting. In addition to the mental and emotional labor required to hype yourself up to take a chance on yet another Tinder rando in this, the age of dating app burnout, there are also plenty of ways a first date can flop. What if there’s zero chemistry? What if they’re a catfish who looks nothing like their profile? What if they secretly have off-color political opinions or are rude to waiters? WHAT IF YOU HAVE NOTHING TO TALK ABOUT?

I hear you on literally all of the above—except that last part. Take it from me, a woman so perpetually single and seeking that I have been on, oh, IDK, several thousand or so first dates: Date number one is the easiest time you’ll ever have making conversation with another human being—or at least a relative stranger. Why? Because first of all, you’ve both agreed to be there, which means you’re probably both at least somewhat invested in making this not a complete waste of each other’s time. Also, you most likely know little to nothing about each other, which means literally all you have to do to make conversation is ask each other questions. That’s it folks—the big secret to first-date success (or at least to avoiding a total first-date fail) is just asking each other stuff.

Of course, no one wants a date to feel like an interrogation or, like, a tipsy job interview. Which means you’re gonna wanna make sure you’re not just firing off a list of obviously rehearsed first date questions but actually *listening* to the answers and using this little Q&A as a jumping-off point for a more in-depth tête-à-tête. And while I’m a strong believer that most “rules” about things you shouldn’t talk about on a first date (religion, politics, exes, etc.) are a bunch of archaic nonsense, it’s always a good idea to read the room and be mindful of what you’re asking. You know, pretty standard interacting-with-other-people-in-a-society things.

If you need a little help figuring out what to ask, have no fear—we’ve kindly gone ahead and put together this list of 29 first date questions for your inspiration. From the basics to deeper Qs to pull out if you’re feeling bold, one of these well-placed questions is sure to fill any awkward silences you stumble into. Good luck!

1. What are your favorite and least favorite things about your city?

2. If you had to live somewhere else, where would you go?

3. What’s one thing you’re really good at and one thing you’re really bad at?

4. What TV show are you watching right now?

5. What was the last TV show you were truly obsessed with?

6. If you could only listen to one song for the rest of your life, what would it be?

7. What’s your biggest priority outside of work?

8. How did you decide to do what you wanted to do for a living?

9. Do you like your current career path or do you see yourself pursuing something else in the future?

10. Where is the next place you plan to travel/want to travel?

11. Who is your oldest friend and what’s your favorite thing about them?

12. What was the worst date you’ve ever been on?

13. What made you want to ask me out/go on this date?

14. What’s one thing you want to know about me but are afraid to ask?

15. What’s your most controversial opinion about dating?

16. What’s the weirdest thing you’ve ever done on a first date?

17. Who was your first crush?

18. Who is your current celebrity crush?

19. What’s your sun sign? (Bonus points if they also know their moon!)

20. What’s one thing everyone else seems to love that you think is totally overrated?

21. What are your favorite and least favorite things about your job right now?

22. What’s the riskiest thing you’ve ever done?

23. What’s your number one deal-breaker in a relationship?

24. What’s your drink of choice?

25. What’s one thing you’re really attracted to in a romantic partner?

26. What do you think is your best quality?

27. What’s one book you think everyone should read?

28. What’s one thing you wish more people understood about you?

29. How do you feel about kissing on the first date? (Best asked at the end of the date if you’re hoping for a 😘.)

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