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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.

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 ann arbor speed dating first date? 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.

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!”

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 or her true personality. What are their likes and dislikes, what do you have in common, what does he or she do in their spare time?


Depending on the above answer, ask what they’re watching, or what they’ve seen lately.


Have you traveled anywhere cool lately/do you have any trips coming up?

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.

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

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

27. Do you have a big group of friends?

Time to seal the deal—the last few minutes of a date are crucial to make ann arbor speed dating over 50 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. Okay, can I at least leave the tip?

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?

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

The 1960s television show The Dating Game featured three contestants who competed for a date with a bachelorette. As the bachelorette could not see the contestants, she based her choice entirely on their answers. The game was silly and creative, and it gave viewers some playful ways to interact with the opposite sex.

While you could turn this into a fun party game if you're hanging out with a bunch of other singles, you could also use a list of dating questions like this to get to know someone you're already interested in but don't know that well.

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