30 Questions to Ask Your Crush That Are Actually *Very* Insightful

·14 min read

A few strange things happen when you develop a new crush: You can't fall asleep without envisioning your future wedding, your tongue seems to swell up anytime you're within their vicinity, and making casual conversations feels low-key impossible.

But here's a hint: Asking a few really, really good questions can help break the ice and ignite the back-and-forth banter we all love when getting to know someone.

That said, you can't just ask any question though. You have to be sly when digging for info from your crush. You need the questions to be deep enough that you can get to know them, establish a connection, or test the waters to see if they're into you as well, explains Carmel Jones, a relationship coach and sex expert at The Big Fling. But you also don't want to come across like you're interviewing them for a job.

So to help you on this journey, we've come up with the best, juiciest conversation-starting questions to ask your crush the next time you want to chat. Thank me later.

1. "If money wasn't an issue, what would you do?"

This Q builds curiosity and exploration, which is why licensed marriage and family therapist Payal Patel loves this question. Pay attention to what they would love to do if they didn’t have financial restrictions, which can indicate what they value and how they truly enjoy spending their free time.

2. "What is one rule you really enjoy breaking?”

“Breaking rules is sexy and taboo, but there’s a limit,” says psychologist Kassandra Heap. Maybe they like sneaking an extra sample at Costco or speeding on their way home from work. This question not only gives you a peek at where your crush’s moral compass lies, but it will also help you determined whether it aligns with yours (which can seriously alleviate future, potential disagreements).

3. "Your kidnappers would return you for talking about _________ for 2 hours”

Not only is this question a unique way to mix things up, but Heap says it’s also a great way to tap into your crush’s hobbies. “It’s always fun to hear someone talk about something they are passionate about, and it gives you a glimpse of the type of things they find interesting,” she explains.

4. "What's the one place you have to travel to before you die?"

Many people grow individually by traveling and learning about different cultures, says Patel, which is why uncovering whether or not your crush is more of an explorer or homebody is pretty major. Obviously, if you like to travel, you’ll want to know if your crush will be down to country hop, but chances are if they value taking trips, it shows they’re down to veer outside of their comfort zone and enjoy being adventurous.

5. "If you had to eat the same meal every day for the rest of your life, what would you eat?”

First of all, talking about food is always interesting, and the convo might even end with both of you getting so hungry you order Taco Bell. Yay! More importantly, however, is how your crush answers this question, says Heap.

“Are they responding in a thoughtful, curious, or engaged way? Or are they responding in a dismissive, nonchalant or disengaged way?" She asks. "If they aren’t willing to play along, that means something.” If they’re giving you nothing answers, it’s a sign they might not be as game for playful convos/experience, which could make future road trips superrrr boring.

6. "If your life was a TV show, what would the theme song be?”

This is so much more fun—and meaningful—than asking someone what their favorite song is. Would their show be a drama? A sitcom? A limited series? And is the opening music lively and peppy or more sorrowful and Big Little Lies-ish? This shines some light not only on what tunes your crush listens to but how they view the story of their life. Deep, right?

7. "Have you ever been to therapy?"

Obviously you’ll really want to read the situation before jumping into this question since it’s a bit deeper, but Patel says if the mood is right, this Q can be extremely powerful and telling.

“Therapy shows they’re not afraid to seek help and they’ve opened up a space for individual growth,” explains Patel. “People tend to go to therapy to become better versions of themselves, and that carries over into any relationship.”

8. "What's something you're really looking forward to?”

Whether or not you asked the deeper therapy question, asking some Qs that are positively framed can create a more relaxed and enjoyable conversation, says Heap. “Being on the receiving end of too many serious and intense questions can feel like an interview,” she explains. “Lighten up the conversation with a few questions like this to create a comfortable atmosphere between you and your crush."

9. "What is the worst date you’ve ever been on?”

If you want to sniff out some red flags (or hopefully lack thereof), Heap says asking about bad dates is a solid place to start. “This question is a must because it gives you an idea of what someone considers characteristics of a bad date and in turn a non-ideal partner," she explains. "It also tells you in the inverse what they think is a good date.”

10. "What’s your favorite story to tell about your best friend?”

One of the easiest ways to get someone to open up about themselves is for them to talk about, well, not themselves. “This question lets you know what sorts of things your crush admires in others," Heap explains. “Also, we’re often the sum of the company we keep, so you can assume your crush has behaved in similar ways as their best friend in their story,” or at least cheered on their behavior.

11. "Who is your celebrity crush?"

This question lets you get a sense of their taste in other people and the things they find both ideal and attractive, says Jones. It doesn't have to be super formal when you ask—you can bring up an artist or movie star you really like, and then pivot from that to, "They're my celeb crush, who's yours?" Ya feel? Sneaky!

12. "What's your biggest turn-off?"

Or what behaviors can they absolutely not stand? "As important as it is to learn what they are attracted to, you'll also want to know what turns them off," adds Jones. Again, feel free to couch this like a rando celeb opinion of yours. "I can't stand Leo DiCaprio," you say, and when they ask why, you can be like, "He's a smoker, which I just can't vibe with. Who's your Leo?" Sneaky pt. 2!

13. "What was your first impression of me?"

There's a chance that your crush's first impression of you was actually that you were crushing on them, but nevertheless, it's a great opportunity to figure out what they think about you, according to Jones. Set it up like, "People always think I'm super shy, but I'm not," or vice-versa, sub in any adjective for shy. Then they'll probably offer up a rejection or affirmation about your statement, or you can press them like, "What did you think?"

14. "Do you like huge parties or would you rather spend time in a small group/alone?"

Figuring out if your crush is an introvert or extrovert can make judging your potential compatibility way easier. If you absolutely must go out five nights a week and they're the kind who doesn't leave the house unless absolutely forced, it miiiiiight not be a great match. Being able to suss out your crush's comfortability in social situations and how they recharge means you can also make them comfier in the future, according to Jones. If you know they're shy, maybe don't go for the OTT, public declaration of love in front of all your mutual friends, but if they are, do it!

15. "What's something weird that you find attractive?"

Maybe it's something physical like elbows, or maybe it's more abstract like when someone is willing to take one for the team in a group setting or something. Everyone has weird things they're into that aren't necessarily, "universally attractive," explains Jones, but getting to know these quirks are helpful in seeing what your crush values and for your future relationship.

16. "What's the best gift you've ever received and who was it from?"

Not only is this primo intel for any future gifting you'll be doing if you become a happy couple, it also tells you what and who matters most to your crush, says Jones. Was it a rando gift from an acquaintance where just the thought was what counted? Or was it a super elaborate gift from their BFF?

17. "What's one rule to live by?"

Get a sense of what they value most in life and what they consider to be important life lessons with this one, explains Jones. Is it to always treat others with kindness? Is it that they should do no harm? There are no wrong answers here, and the insight, even aside from them being your crush, will likely stay with you, just because it's an interesting question most people don't get asked.

18. "What's your biggest fear?"

The answer could be anything from spiders, to death, to heights, to ghosts. This question gives you space to bond over something, even if you're not afraid of the same thing. "Secrets and fears tend to strengthen the bonds between people," Jones says.

19. "Who are you closest to in your family?"

This lets you learn about your crush's family history but also opens the door for lots of organic follow-ups, according to Jones. If they say they're closest to their mom because she's the kindest, you can ask for an example or their favorite memory of their mom being the saint that she is. If it's their sibling, ask why. If it's their grandma because she's strict but wise, ask for more deets. You get the picture. People like talking about their families usually, so you're opening a door to let them talk that they'll probs appreciate.

20. "Do you want to be in a relationship right now?"

Yeah, most questions you'll wanna ask your crush aren't yes or no questions, but this is the one exception. "Your time is valuable and if they say no, you might want to re-evaluate whether or not the pursuit is worth that time," says Jones. If you're looking for an easier way to thread this into the convo, try bringing up how you're simply exhausted of dating and considering taking a break from everything. Then you can segue into asking them, "How about you, are you dating? Do you want to be dating right now?"

21. "When was your last relationship?"

Piggybacking off the nice lil segue into ~dating~ as a topic that #5 just opened up for you, you can press a bit further and get the scoop on their last relationship, why it ended, and more. This question is a goldmine, says Shelly Kessinger, LPC, of Friendswood Marriage Counseling, as it can help you understand who this person is and how they operate in relationships. Not only will it tell you how much time has passed since their last relationship and get a timeline (exactly what you're asking for on the surface), it'll also help ease you into the next two questions which get progressively harder and aren't as simple to answer.

22. "Why did it end?"

Next, you can get some deets on why the relationship ended. You can gain insight on everything from whether or not they're self-aware enough to notice patterns in their relationships, if they refer to their ex as "crazy" (red flag: beware the person who calls their ex crazy as they might do the same for you). Through this question, you can get a sense of their perspective and see how they are talking about it. "Do they seem still angry? Bitter? Relieved? Annoyed? This can be helpful to see how emotionally available they are, as well as give you an idea of what their dealbreakers are," adds Kessinger.

23. "Do you think you're over your ex?"

For the pièce de résistance, ask this question to see if they're truly ready for a relationship. "The obvious answer is, 'Yes, I'm over my ex,' but there is an opportunity for self reflection, self awareness," says Kessinger. This question gives them space to communicate their feelings to you, and even possibly segue into how great you are. The key here is to listen for bitterness, resentment, and annoyance when they answer, Kessinger says. "The way they answer is just as important as what they actually say."

24. "What's your love language?"

If you don't know your love language, get on it pronto! Learning your crush's love language opens the door to allowing a deeper connection without emotionally exposing yourself too soon, explains Chloé Miller, founder and CEO of "And, Swipe Right," a Chicago dating consultancy. "This is how people have those 'they just get me' clicking relationships," she adds. "Communicating in the other person's 'language' makes them feel seen, heard, and emotionally validated. It's flattering, deepens your bond, and because it's enjoyed, [they'll] be back for more."

25. "What do you do to relax?"

Everyone's got a different way to recharge, and similar to finding out if they're an introvert or extrovert, seeing if you're on the same page about how you both re-up your batteries can be something you bond over. If you both love something similar like going to yoga, you can even take this as an opportunity to go together, adds Miller. It doesn't have to be a date-date either if you're not at this stage yet, just "going together" can plant the seed in their head that it might be fun to hang with you outside of your normal interactions.

26. "What's a typical Saturday look like for you?"

Adding another layer to the "what do you do for fun," question, this one lets you also get more insight into who the person is. This question can also surface dealbreakers, says Miller. Do they spend almost every Saturday catching up on work? And if so, are you okay dating a workaholic?

27. "When it comes to priorities like work, life, family, and friends, how does each rank compared to the others?"

This question is risky because if you don't align on the important stuff, it might be a signal that it's time to nip this crush in the bud and settle for being friends. However, if you find instead that you have commonalities in your ways of thinking and prioritizing, "bring these up in conversation and emphasize your values and how important each is to you," suggests Miller. "Values are great to bond over as it defines a person's character."

28. "How would you spend an ideal fake sick day?"

If someone does spend every Saturday working out of obligation, what do they want to do for fun? This lets you know how your crush would plan a hypothetical frivolous day off, and it's also super fun to hear about. "If you bring up fun ideas, it's a new bonding point for you two and the conversation just keeps getting better," Miller says.

29. "Are you a dog or cat person?"

This is also another exception to the "no one-word answers" rule, as people have VERY strong opinions on this baby, and you'll def be going back and forth for a while on it. "This is a surprisingly polarizing question and it's good to have an opinion," says Miller. It might be a seemingly innocent and superficial topic, but think of the ways you can build conversation around this. "Funny memes, cute videos, heartwarming stories...the point here is to bond on something that keeps you two chatting IRL and online."

30. "What's your most embarrassing moment?"

The point of this question isn't so much to use the info that they share, but to get them to laugh — the bigger the belly laugh, the better. Genuine laughter releases dopamine, a neurotransmitter, which increases emotional connection, and makes it more likely for you both to stay engaged in convo longer, according to Indigo Stray Conger, an AASECT certified sex therapist based in Colorado.

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