25 First Date Questions That Work Every Time


Dating can be a real pain. There is nothing more stressful than the first date, especially if it’s with someone you don’t really know. Sure, they’re meant to be a precursor to an actual relationship, but first dates are also mini interviews disguised as social outings, whether we like to admit it or not. That’s why first date questions are so important!!!

If you come with a ready set of questions to ask, there won’t be any awkward silences between you two. If you’re savvy, you’ll realize that certain questions–even the most basic ones—have the ability to tell a lot about a person. Here, I’ve divided your hypothetical first date into five phases and suggested a series of questions to ask during each.

Phase 1: The first 10 minutes

These questions are key primers, the ones to ask after you’ve said hello, and settled in somewhere comfortable. They might be a little boring but it will give you immediate things to talk about and you’ll learn the basics about them.

1. What do you do, and how long have you been doing it?
2. Where are you originally from?
3. Where did you go to school?
4. What was your major?
5. Where exactly do you live in [insert your city or town here]?

Phase 2: After the first drink arrives

Now that you’ve gotten the primers out of the way, it’s time to get a tad more specific. Questions over the first drink should be an equal mix of inquisitive and casual, and should allow you to start gauging his true personality. What are his likes and dislikes, what do you have in common, what does he do in his spare time?

6. What do you like to do when you’re not working?
7. Are you more of a TV person, or do you prefer movies?
8. Depending on the above answer, ask what they’re watching, or what they’ve seen lately.
9. What type of music are you into?
10. Have you traveled anywhere cool lately/do you have any trips coming up?
11. Have you read any good books recently?

Phase 3: Things are starting to get comfortable…

If you and your date are really starting to hit it off, it’s time to start slipping in some slightly more personal questions, while making sure neither of you feel compelled to reveal too much. Some of these questions may seem silly at first, but they can be very telling. They’ll also further loosen the two of you up and can lead to some funny, entertaining conversation.

12. Are you a cat person or a dog person?
13. Do you have any siblings?
14. Coffee or tea?
15. Where else would you consider living?
16. What’s on your bucket list?
17. Do like to cook?
18. Do you like your job? What do you want to do next?
19. What’s your social life like? Do you have a big group of friends?
20. Do you consider yourself career-driven?
21. When’s your birthday?

Phase 4: Sign Me Up for a Second Date 

Time to seal the deal– the last few minutes of a date are crucial to make sure he asks you out a second time. If you think the date went well, don’t be afraid to let him know. The final questions should easily transition you out of the date while subtly implying that you’d be down to meet up again.

22. Can I split the check with you? Okay, can I at least leave the tip?
23. Do you have any fun plans for the rest of the weekend?

Phase 5: Let’s Keep the Date Going

This phase is tricky, and should only be reserved if you’re really feeling strong vibes. If you’re confident, ask if he’d  like to continue the date someplace else. Suggest a (PG-rated!) alternate ending to the night rather than simply going your separate ways after drinks or dinner.

24. There’s this cool bar I know around here, want to go grab a drink?
25. Want to get coffee/dessert after this somewhere else?

What do you think? Ready to get out there and put these questions to the test? What other questions would you ask on the first date? Let me know in the comments below!



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