Jacquie Boyd/ Getty Images
Alyssa Thorne
November 16, 2016 3:19 pm

You know what is a big barrel of not that fun? Dating. Between the constant ebb and flow of dating apps, the never-ending mixed signals, and the fact that American men struggle to dress themselves so desperately, it’s kind of a nightmare. Maybe the most difficult thing, though, isn’t just finding somebody you could see yourself with — it’s finding somebody who you want to get serious with, who also wants to get serious with you. We’ve put together our top five first date questions to try to help you suss out if your next date is somebody you could both go the distance with, and sing along to Hercules’ “Go the Distance” with, if that’s your thing.

We also fully acknowledge the irony of using Bachelor in Paradise GIFs in a story about finding a legit relationship. Do as we say, not as we watch.

1. Are you more of an introvert, or an extrovert?

You might not want to ask outright — it’s kind of an odd question, and you’ll probably get a reasonably good read on this throughout the date — but it’s a good thing to know about a person. Even with friends, if you’re a hardcore introvert who needs a lot of time to chill on your own and recharge, maintaining relationships with people who need constant contact and don’t have that impulse can be difficult, and requires excellent communication. What might be a simple “I just need some down time to recharge” to an introvert can sound like “I’m blowing you off” to an extrovert, if both parties aren’t open and upfront about their needs.

While “hey, are you an introvert or an extrovert?” might not be the way you want to go (totally up to you), asking related questions like “what’s your ideal way to spend a Sunday?” or “are you a big party or small group kind of person?” can give you a better idea of how well your lifestyles are going to mesh. Not remotely trying to imply that introverts and extroverts can’t or shouldn’t date, obvi, it’s just good to know how to read interactions if you’re trying to build a solid foundation going forward.

2. What’s your favorite place in the whole world?

It’s one of those questions that has nothing to do with the question. Asking somebody what their favorite place in the world is can tell you a lot about them. It’s a really broad question that can have so many answers, and can give you a good idea of what kind of environment your potential partner feels most comfortable in. It also will show you what’s important to them. Somewhere faraway and exotic? They’re adventurous (or just trying to impress you). Somewhere related to their youth? They’re probably close to or comfortable with their family and like the familiar. Related to a specific person or event? Now you know one of the points around which their life pivots.

Having similar values to your significant other is a huge part of building a healthy relationship, and since being like, “yo, what are your values?” might feel too blunt, this is a good conversation starter and gets you some good insight.

3. How do you like to spend your free time?

The first few weeks, or maybe months if you’re lucky, of a relationship can be exciting. You’re both trying to impress one another. You’re going out to dinner, to bars, to museums, to parks, doing all the cute coupley stuff. But once you settle in, you know what your relationship becomes? Mostly free time. Not carefully planned dates or day trips — although some of those, too — but a lot of that empty space in your schedule that usually belongs to you is now shared to whatever extent with another person. So it’s important to know how this person spends their empty space, so that if you do end up in a relationship, you don’t realize that you’re entirely incompatible after a few short weeks.

Are you a Netflix binger? A hiker? A crafter? A gamer? Some combination thereof? It’s a super simple question to ask somebody on a first date, and can also go far to start conversation over what you have in common. But if the person you’re with is hardcore outdoorsy and spends every weekend hiking twelve miles into Sequoia National Forest to have a true rustic experience, and your idea of a weekend away involves hotel pillow mints, and you like it that way… this is maybe something you should take into consideration. Also, hi, you need to know what they watch on Netflix, because there’s nothing more tragic than dating somebody for two months before finding out they have a very different idea of quality programming.

4. Where did you grow up?

Real talk, move to LA from anywhere on the east coast (we’re sure the reverse is true, but just speaking from personal experience) and the culture shock is REAL. People here think red vines taste good, actually enjoy having no seasons, have no idea what a bagel is supposed to taste like, and get cold once it dips below 75 degrees. It’s a DIFFERENT WORLD. This country is enormous, and the experiences one might have growing up are correspondingly diverse. Family, economic status, region, sports team, whether or not you would get disowned from your hometown for not caring about a sports team (#STEELERSNATION)… these are all big components of what make you, you.

Since it can sometimes feel intimidating to ask about somebody’s family if you don’t know them very well, asking where they grew up doesn’t only give you insight — once again, into their values, priorities, and experiences — it also leads into a conversation that will likely give you enough information about their family to ask questions about that, which is important. Whether or not somebody is close with their family isn’t a red flag, but how they speak about their relationship with their family could be.

5. WHAT THE HELL ARE YOU LOOKING FOR?

We young folks increasingly live in a dating world where it’s not ~cool~ to ask after somebody’s intentions. We’ve got to stop this, guys. We’re not here to crusade against hookup culture or whatever older generations want to complain about us doing — if you want to have lots of sex and not have a serious relationship, more power to you. You should only engage in relationships that bring you joy or fulfillment. But you should also be upfront about it. So if you’re looking to find something serious and long-term, you should probably make sure the other person is looking to do so, too.

It’s a scary question to ask, and striking the right balance so that it doesn’t sound like you’re picking out china patterns after you first coffee if important, but it needs to be done. One of the biggest roadblocks to finding a serious relationship when you’re young is frankly that a lot of young people aren’t looking, for better or for worse. Let’s make it just, like, an expected part of a first date: Establishing expectations openly and honestly early on.

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