Questions for First Dates

The best way to make the conversation flow on 1st dates is to come prepared with questions planned in your head.


This is the third blog post from our three-part series on first dates. While the last two armed you with what to do and not to do on a first date and 28 fun activity ideas, this offers 40 progressive questions to use throughout the date. We hope this little series will charge your get you geared up for your big Saturday night date!

Dating can be a really difficult experience and nothing is more awkward then that first date with someone you barely know. However difficult they may be, pretty much every relationship starts with one. While they are not interviews per se, this is where you find out if there is chemistry between you and your date. The best way to make the conversation flow, while still learning enough to see if they are a potential partner, is to come prepared with questions planned in your head. The following questions from StyleCaster break the date down into five phases with appropriate questions for each. These are geared toward women asking men, change the pronouns for your context.

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. Sure, they’re kind of snoozy, but they’ll set the tone for your date, and give you immediate things to talk about: “Oh, you went to Notre Dame? So did my cousin!”

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. If you could only eat one thing for the rest of your life, what would it be?

14. Do you have any nicknames?

15. If you won the lottery tomorrow, what’s the first thing you’d buy?

16. Do you have any siblings?

17. If you could be any person for a day, who would it be?

18. What’s your biggest pet peeve?

19. Coffee or tea?

20. Where else would you consider living?

21. Are you as tired of KimYe as I am?

22. Do your parents still live in the house you grew up in?

23. What’s on your bucket list?

24. Are you a morning person or a night person?

25. Do you ever cook?

26. Do you like your job? What do you want to do next?

27. What’s your social life like? Do you have a big group of friends?

28. Do you consider yourself career-driven?

29. What are you most passionate about?

30. 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.

31. Can I split the check with you? Okay, can I at least leave the tip?

32. How is work looking for you this week?

33. Did you like this place?

34. Do you have any fun plans for the rest of the weekend?

35. Do you have a busy week coming up?

36. How are you getting home?

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.

37. There’s this cool bar I know around here, want to go grab a drink?

38. Want to get coffee/dessert after this somewhere else?

39. My friend’s actually having a party a few blocks away, do you wanna stop by?

40. What are we doing after this?

…via 40 First Date Questions That are Foolproof | StyleCaster

We hope you have found this three post series on strategies for dealing with first dates useful. Just remember, in the wise words of H. Jackson Brown Jr., “Sometimes the heart sees what is invisible to the eyes.