3 expert-approved questions to ask your crush to save yourself from the depths of awkward silence


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One night, like a vulture wearing red Minnie Mouse heels, I cornered my crush outside a music venue and began to, essentially, interview him. It started normal enough—”Hi, it’s Mary Grace from the party, what’s up?”—but then, out of the blue, I asked, “Were you popular in high school?” I don’t know why, of all the possible questions to ask your crush, I went with that. Subconsciously, I’m sure it’s because I know I could only ever be with someone who sat at the Weird Kids’ table, but still. Weird flex on my part. While things ultimately ended up in my favor (we’ve been together for over a year), he still brings up, “Were you popular in high school?” like a joke.

Here’s the thing, friends: It’s difficult to get to know to a person you’re interested in. Maybe it’s someone you’ve been having banter with on a dating app, or maybe it’s a friend of a friend who you think is cute, yet you can’t get a moment alone with them. Or maybe it’s the person with whom you already have first-date plans set—or at least it seems date-y? But you’re not totally sure. (Is it a coffee date or just coffee?) Regardless, knowing the right questions to ask your crush is tough.

Regardless of whether there’s legitimate relationship-worthy promise with the crush in question or they’re just a moron you’re biologically drawn to, relationship expert Susan Winter has a few questions to ask a crush you can always feel confident about posing.

1. “Does someone think they’re in a relationship with you?”

Anyone who doesn’t understand why a question like this is important has never tripped and fallen face-first into someone else’s open relationship. Because the modern dating landscape is so, um, limitless, exclusivity and boundaries feel like a thing of the past. I’ve had love interests tell me, “I’m not with anyone,” and that ends up just being code for “I’m not with anyone tonight, but get ready for some poor 22-year-old with Manic Panic hair to make passive-aggressive conversation with you at a party after she sees us together.” God, being single was fun.

“Your partner may not be telling you the total truth on your first dates,” Winter tells me. “They don’t consider themselves involved—but, someone else does. That’s important. You will have to deal with this other person if you choose to move forward with your date.”

2. “So, have you always been a model?”

So great news: Your suitor is an absolute babe who hit the genetic jackpot. We can pretend we’re not shallow and all, but there’s something very gratifying about showing your friends your crush’s Instagram page and not having to be like, “No, they’re way cuter in real life.” Unfortunately, many tie really, really, really, really ridiculously good looking people with being selfish and conceited. So taking this lighthearted approach may break the ice in a flattering way that communicates you’re attracted to them but also not intimidated.

“See if your date has a good sense of humor,” Winter says. “If they can laugh at themselves, they’re down to earth. That’s a desirable quality.”

3. “When do you feel most alive?”

A key strategy for effectively connecting with people is allowing them to open up and talk about their favorite subject: themselves. Seriously, most people can’t get enough of talking about themselves. Maybe not Keanu Reeves, but, like, everyone else. What’s great about this question is that it’s personal and really allows your object of affection to light up as they tell you what makes them tick.

“This question gives you insight to the dreams and passions of your date,” Winter says. “It’s essential if you want to ‘find’ their heartbeat. If you’re looking for a meaningful connection, you have to know what makes them feel alive.”

So once you know that your crush, say, has a very violet shrine to Prince in their room, you’ll have a more precise read as to what to talk about and ask during future conversations. (Like maybe, “Did you know that Prince always smelled of lavender?”). And if the relationship goes really long-term, you can pocket the answers to these questions as ways to inform what to do on future dates. Also, gift ideas for Christmas. And Valentine’s Day. And like two birthdays. Three birthdays might be getting a bit ahead of yourself.

If you get that first date in the books, here’s why a coffee shop is the ideal meet-up spot. And once the romance has heated all the way up, this is the right time to spill all your secrets to your new S.O. 

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