10 First Date Questions To Ask That'll Help You Figure Out Your Date's Real Intentions

by Cosmo Luce

The first date is a delicate game, but asking some first date questions to figure out what your date is really, truly looking for can prevent you from acquiring injuries from playing the field. Whether you want true romance or just a one-night stand, it's better to figure out if the two of you are on the same page — and it's never too early in any relationship to establish strong, clear communication.

At the same time, you don't want to have a conference or a debriefing on your first date. You want to flirt! You want to be witty! You want to seduce them with minimal effort! And you (maybe) want them to call you next week! That's why humor is the best way to feel out your first date. At the center of every laugh is an element of truth, so you'll be able to feel out your first date's true intentions with how they respond to your lighthearted jokes. Plus, you'll be able to figure out if they are a humorless sourpuss ahead of time.

Here's what to ask your date if you want to figure out where they're coming from, but you don't want to show all of your cards.

1. "How Often Do You Go On Awkward Dates With Someone On Tinder?"

Maybe a bit direct, maybe a bit brusque, but I never really believed in beating around the bush. Your first date's response to this question might be revealing, or it might give you nothing. They might meet up with people on Tinder all the time for one-night stands, or you might be their first-ever date. If they respond with something like, "I don't normally meet up with that many people, but I seemed to really click with you," then you know that you have their interest.

2. "Your Pick-Up Line Was So Smooth, What's Your Secret?"

This is a great question if you suspect that the person you're going on a date with is a professional flirt. Those sexy one-liners always give me cause to raise an eyebrow when we match, because I generally assume that they use it on everyone. If they admit that their friend fed them lines to improve their dating game, then you're probably on a date with a softie posing as a genuine player. I'd sign up to see them again.

3. "So What Other Cute Date Spots Do You Have In Your Rotation?"

This question allows your date to give you the benefit of the doubt and assume that you're just trying to figure out plans for a second meet-up. At the same time, it gives you some insight into whether or not you are one of a few different dates in constant rotation.

4. "Would You Rather Fall In Love Or Have The Most Amazing One-Night Stand?"

While you definitely should not pull out this question as a non-sequitur, if you and your date are already talking about relationships or swapping one-night stand stories, then it's perfectly fine to pull out this question. There are lots of people out there who are getting tired of sleeping around and looking to settle down, and there's no shame in asking.

5. "I Take It You Don't Have A Cuff This Season?"

It's funny, it's topical, and it is as good of a way of asking, "Are you really single?" without being blatantly obvious. Plus, if you suspect that your first date is really just shopping for a side piece to spice up their open marriage, their response should give you plenty of heads up. Nothing can make you back out of a second date like someone dropping, "Actually, I do have a wife," on you halfway through dessert.

6. "You're Really Cute, Can You Please Say Something To Disenchant Me?"

Hopefully, they will say something charmingly deprecating that will make you crush on them even harder and not start telling you about their past infidelities, weird fetishes, and restraining orders.

7. "What I'm Always Wondering Is, Why Go On Dates When You Can Have A Cat?"

This is a genuine question, and also, it's a good way to figure out whether they are just looking for a flood of post-coital chemicals to elevate their mood or if they're actually interested in having a human around whom they can talk to.

8. "What's Your Preferred Method For Getting Out Of A Second Date?"

You're presumably asking questions because you want to get a read on your date and you want to know what to expect, so you might as well do some detective work to determine whether you're spending time with a serial ghoster, with a breadcrumber, or if you've actually managed to encounter one of the rare human beings who won't completely flake after a single outing — in which case, you should cling as tightly to them as you possibly can.

9. "How Has Love Treated You So Far?"

It's lighter than asking something like "Want to tell me what happened with your last girlfriend?" or getting entrenched in rehashing your breakups, but it still will give you insight into whether you're on a date with somebody who is open to where things go or if they prefer to avoid having emotions at all costs.

10. "Do You Want To Kiss Each Other Goodbye And Then Never See One Another Again?"

Save yourself the trouble of leaning in at the door if they're just going to lean away.

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