No secret here—dating can be a real pain. Nothing’s more nerve-wracking than a first date, especially with someone you hardly know. And while, sure, dates are meant to be a precursor to an actual relationship, first dates are also mini-interviews disguised as social outings, whether we like to admit it or not. That’s why figuring out what to talk about ahead of time with a list of good first date questions and conversation starters is so important.
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A foolproof way to ensure that conversation will always be flowing is to simply ask your date things, although—given the fact that we never know how comfortable others are with casual conversation—that might be easier said than done. The trick to successfully vetting a prospect on a first date, while simultaneously keeping the energy light and fun, is knowing what questions to ask and how to ask them. For example, work, his or her family, hobbies, pop culture, and favorite music are all surefire bets. Four things never to ask her or him about on a first date? Politics, religion, exes, and salary. Too serious, too fast!
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, we’ve divided your hypothetical first date into five phases and suggested a series of questions to ask your date during each.
Phase 1: The first 10 minutes
These first date 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]?
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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 their true personality. What are their likes and dislikes, what do you have in common, what does he or she do in their 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?
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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 (or another celebrity couple) 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?
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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 a second date happen. If you think things went well, don’t be afraid to let him or her 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?
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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 she or he would 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?
A version of this article was originally published in 2016.
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