9 First Date Questions That'll Keep You & Your Date Talking All Night

by Alison Segel

First dates can either be incredibly natural or frustratingly awkward. It all comes down to chemistry and the nature of the conversation between you and your crush. But what are some first date questions that'll actually help you to get you know someone, while still leading to an actually stimulating conversation between you two? I never really know what the hell to talk about when I show up to a date with someone I like. Actually, my mind kind of goes blank, and my whole personality disappears. It's this fun superpower I have.

My actual nightmare is asking a question that will lead to a conversation-stopping yes or no answer. Or gosh, even worse, what if we somehow start talking about the weather? "Yes, it has been hot outside lately, great observation." That'll make a date go nowhere fast. There's obviously some magic to having a dialogue that's fun, flirty, and informative. But what is it?

Well, through a lot of trial and error — mostly error — I kind of figured it out. So here are some first date questions that'll keep you and your date talking all night. (And hopefully, at the end of talking, you'll end up liking each other.)

1. "What's Your Funniest Childhood Memory?"

Talking about your childhood brings up a sense of nostalgia, and nostalgia makes people happy. If you're able to have a deep conversation with your crush that brings up positive, good emotions, they'll associate them with you. Although, my funniest memory is when I ate a tuna fish sandwich before a school play, got food poisoning, and then threw up on stage, so that's not really a good first date story I guess.

2. "What's Your Favorite Kind Of Pizza?"

You can always get into an argument about whether or not pineapple belongs on pizza, which is fun.

3. "How Would Your Friends Describe You?"

This is also a good way of finding out whether or not your crush even has friends.

4. "Do You Cry During Movies?"

I, for one, love a man who feels comfortable crying when Dobby the House Elf dies in Harry Potter.

Woops, spoiler alert.

5. "Have You Ever Broken A Bone?"

I've never broken a bone, so I just find it interesting to ask this question. How do people break bones? What did it feel like? Did people write on your cast? I always wanted a cast, so people could draw pictures on it. I dunno!

6. "Would You Ever Go Sky Diving?"

You might not realize this, but knowing whether or not someone would go sky diving is a huge indicator of your compatibility. For example, I could never date someone who wants to jump out of an airplane. I hardly like getting off my couch, so the idea of going out with an adrenaline junkie causes me an undue amount of stress. So figure this out early. Plus, if they are the active type, they'll probably have a lot of good stories to tell.

7. "What Are You Most Grateful For?"

Being able to express gratitude in your life is an integral part of showing appreciation for things and experiencing joy. If you don't know gratitude, it's hard to truly be happy. So A) make sure that the person you're on a date with has a deep appreciation for the good things in life, and B) figure out early what those things are. If your crush is only grateful for material possessions, then they might only be looking for a superficial relationship.

8. "What Are You Most Attracted To In A Person?"

Because I can change for you! I swear! (Kidding, don't actually change yourself for anyone, please.)

9. "What's Your Biggest Turn-Off?"

It's always interesting to find out what turns people off, because these qualities are usually emotional rather than physical. If you ask someone what they're turned on by, they might say great legs or something silly and superficial like that. However, when it comes to turn-offs, people usually go below the surface. I don't like codependence, for example, or people who are controlling.

This kind of conversation will not only help you have a deeper understanding of your crush and their relationship behaviors, but it will also probably give you some knowledge as to why their past relationships didn't work out, which is a good tool for you when moving forward.

So if you're looking to keep your first date interesting, why not try out some of these questions? They're bound to keep the conversation going and give you some valuable information about whether you and your crush are compatible, which is what you're looking to figure out anyway, right?

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