Try these deep questions to ask your crush.

25 Deep Questions To Text Your Crush That’ll Spark Conversation

And I mean deep.

Originally Published: 
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The thrill of texting with a new crush is absolutely unmatched. Hearing the ping of a new message coming in? Glorious. But occasionally, you might hit the dreaded conversation lull. In those moments, it's good to have some deep questions to ask your crush over text prepped and ready to go — something that will kickstart the conversation and give you a chance to get some real insight into who they are beyond that cute face.

Some of these questions might be hard to ask face-to-face, which is why texting can often be much easier. It gives you a sense of safety and comfort that can help you feel a little bolder about which questions to ask the guy or girl you like over text. And since they have to write their reply, hopefully, you'll get a well-thought-out answer that can offer you some real insight into your overall compatibility, should this crush turn into something more. But because no real relationship can exist solely behind a screen, it’s important to also have these conversations in person when you’re ready to do so. Because how else will you know if you have physical chemistry if you can’t vibe IRL?

If you're ready to get to know your crush on a whole new level, these 25 expert-backed questions for how to get to know someone over text are a great place to start.

1. What Does Your Perfect Day Look Like?


This question is great because not only does it give you a glimpse into the things your crush enjoys doing, but you can also decide if they’re things you'd like to do as well. “It's a great optimistic question to talk about what you could do if you had total freedom for a day [and] could lead to a great conversation starter,” online dating coach Perri Schneider tells Elite Daily. For instance, if someone says their perfect day is scaling Kilimanjaro, you may be like, “I'm out.” But if they say drinking cocktails on a private beach, they might just be your perfect match.

2. What's Something You've Done That You’re Most Proud Of?

Who doesn't enjoy a good ol' humble brag? But seriously, not only do you get to learn something nice about your crush, but you get a peek at their values, according to professional matchmaker and dating coach Laura Jacobs. The kinds of things that give them a sense of pride can be very telling. Is it their rock-hard abs or that time they rescued a kitten from a burning building? Having shared values is a key component of compatibility, after all.

3. What's Your Worst Habit?

I mean, you want to know as soon as possible, right? If it's something you can't live with, better to find this out over text than learn the hard way.

Just note, though, that this question should only be asked if it comes up naturally. “This can be viewed as a judgmental negative question and could lead to bringing the conversation or vibe of your date down,” , Schneider points out. “I don’t recommend asking this out of the blue unless it comes up as something you share personally and then they weigh in.”

4. What Is Something That Really Scares You, But You'd Like To Do Anyway?

“It’s always important to ask what scares someone, as we all fear something,” Jacobs tells Elite Daily. This question can result in anything from cliff diving to falling in love. Either way, this is good info to have so you can see if you're on the same page when it comes to taking risks and going on adventures.

5. If You Could Go Anywhere In The World, Where Would It Be And What Would You Do?

This question is a fun one to ask someone you’re interested in getting to know more, as it’s “good to know their sense of adventure,” according to Jacobs. Find out if this is a trip you'd have any interest in tagging along on. You can also ask follow-up questions about how they like to travel and what they like to do when they're there. Never underestimate the importance of travel compatibility if you’re interested in turning this crush into something more serious.

6. How Religious Are You And What Do You Believe?

This one's a biggie. If you're really serious about this crush, you need to know about their spiritual beliefs and what that means for how they live their lives. It’s not only important to know if your lifestyles are compatible, but also if your values align, as Jacob says. Do they go to mass three times a week? Or do you? The sooner you can get on the same spiritual or non-spiritual page, the better.

7. Who Are You Closest To In Your Life?


Knowing who your partner is willing to open up with is a big deal. As Schneider says, “This is an amazing way to get an understanding of who is important in this person's life and who they hold close to them.” Is it their mom? Their best friend? Or, uh, their ex? With this deep question to ask your crush, you may just get added to their list.

8. What Are Your Top Three Goals In Life?

Not only do you get a glimpse into your crush's potential future, but you can see if their goals are realistic and if they’re doing the things they need to do in order to achieve them. Are they a dreamer who has totally impossible plans for their life and no plans to make those goals happen? “How you see the world drives how you act in the world,” clinical psychologist Dr. Joshua Klapow previously told Elite Daily. “The more compatible your views, the more likely you are to be compatible." Even at the crush stage, it's worth considering long-term compatibility and if your life goals are in sync.

9. What's Something Most People Agree On That You Disagree With?

This can be as simple as thinking that a movie you hated actually rules, or as deep as not believing in the institution of marriage. This question can either result in a fun fact about your crush, or it could reveal major things about your compatibility, so it's definitely worth asking.

Scheider does note, however, that there might be a more fluid way to work this into a conversation than flat out asking it. “I would not right off the bat ask this question — feels too formal,” she says. “Instead, share about something that you really love that a lot of people dislike — for example, pickle juice! Then ask their input, and make sure to segue the convo into getting to know you.”

10. What Are Your Political Beliefs?

The idea that you shouldn’t talk about political leanings in the early stages of dating is so outdated. If you don’t want to waste your time on someone who isn’t aligned with your beliefs, then make sure you’re asking this from the beginning. With the right person, this question should be fine to ask. “This is a dicey question, but definitely important to be on the same page about,” says Schneider. “Luckily, a lot of dating apps have this as a feature, but if you are uncertain about someone's belief, approach the convo from a neutral territory.”

We live in a highly politicized time, when both your political ideology and the strength of those convictions can be make-or-break for compatibility. Knowing how they feel about current events is key, even if you're not a particularly political person.

11. Are You More Modern Or Traditional?

If you're thinking you may want to get into a romantic relationship with someone, you need to know about their values. Are they in line with yours? If they believe in strict adherence to gender roles and you don't, it's better to know that right away. This question by itself is a bit too pointed, but it might work its way into conversations more naturally through other questions. “This is definitely something you can pick up on through someone’s interactions through communicating and spending time together,” Schneider says.

12. What Do You Want In A Relationship?

This one seems pretty obvious, but knowing your crush’s vision of an ideal relationship is a key part of knowing if you’re compatible. What do they expect from their partner? What role do they envision that person will fill? What dynamic will they find fulfilling? Does it sound like you? These are all things you need to know before considering moving forward with them.

In most cases, this kind of question won’t come up when you first start chatting with someone, but not every relationship is the same. “If you’re vibing, some people get deep on the first chat,” Jacobs says. “For others, this can take months. Always go off the social cues and move at your own comfort level.”

13. What Is The Most Romantic Thing Someone Has Ever Done For You?

This question actually offers you more insight than you might think because you can learn about what makes your crush feel the most loved. That said, definitely save it for after the first few dates, as Schneider recommends. “This is a sweet question, but perhaps one that can be reserved for when you are intimate with this person,” she says.

Was the most romantic gesture a gift? Was it a love letter? Was it the time they were whisked away for some quality time? These answers can shine a light on both their love language and if it's compatible with yours.

14. How Important Is Family To You?

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Talk about a biggie. When it comes to deep questions to ask your crush, it doesn't get much deeper than this. For some, family can be everything, and their goals can often be heavily aligned with being around theirs or creating one of their own. It’s important to make sure your goals are aligned, but also to ensure their family dynamic is one you can vibe with.

Plus, chatting about family is a great way to "find out more about that person and their life and their history," Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking previously told Elite Daily. "It makes somebody open up in a nontraditional way.”

15. What's The Best Compliment Someone's Ever Given You?

This question can tell you, in a somewhat roundabout way, what your crush really values and what they're most proud of in themselves. It’s also a great one to use as a first date conversation starter, according to Schneider. “It could lead to a fun chat about the things you are most proud of in your life,” she says.

16. If You Could Change Anything About Yourself, What Would It Be?

Sure, you may think your crush is pretty much perfect, but everyone has insecurities or areas they want to improve in their life. Answering this question requires some vulnerability, and if they're up for it, it shows they’re willing to open up to you. You can also learn if they're an honest and open communicator — important qualities to have in any relationship. If they say “nothing,” then that tells you a lot about them in itself.

Questions like this are good because they really test compatibility and can save you time, as Jacobs explains. “A lot of people wait to ask really deep questions, and then find out months down the line that they aren’t compatible,” says Jacobs. “It also shows if someone has the emotional depth and availability you’re looking for if they answer the question without hesitation or fear.”

17. What's Something That Always Makes You Laugh?

A similar sense of humor is a major point of compatibility, as laughing together is one of the things that can help you get through both the good and bad. Plus, as Jacobs says, “it’s important to find their playful side.” If the thing that never fails to make them laugh also makes you giggle, you're off to a great start.

18. What Cheers You Up When You’re In A Bad Mood?

This question is great for a couple of reasons. When they're having a bad day, their answer can tell you how to comfort them in the best way possible, even if it is just through small things. "The more we can 'micro bond,' where we engage in small actions that keep us connected and strengthen the connection, the more effective and lasting the bigger bonding moments are," Klapow explained.

You can also tell a lot about how they process their emotions based on what they need to improve their mood. Do they need down time, alone and away from everyone else? Do they want a hug and need to connect to shake off the blues? From there, ask yourself how you feel about that. Are you comfortable dating someone who needs space, or on the other hand, more attention and affection?

19. What's The One Thing People Misunderstand About You?

This question to ask your crush provides you with some real insight into how they see themselves. How self-aware are they and what makes them unique? “This question is great for a first date,” says Scheider. “It could lead to a fun convo about each other's quirks.”

20. Where Would You Like To Be Exactly 10 Years From Now?

OK, not to sound like a job interviewer, but this question is actually really interesting and meaningful, because they can answer it however they want — not just about their career. “Questions around how someone envisions their future will give you a great glimpse into what this person's dreams, desires, and priorities are,” Schneider says. Perhaps they’ll say something about how they envision themself lounging on a beach in Bali, getting their pilot’s license, or reading a book in a cozy cabin in the woods.

21. What Is Something You Could Talk About For Hours?

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Everybody has something that they’re a little too passionate about — and that can be incredibly endearing, especially if your interests overlap. “You may like the same music, enjoy the same sports, and explore the same interests," relationship expert Susan Winter previously told Elite Daily. "These similarities form a foundation of natural connection and comfort.”

22. Have You Ever Had Your Heart Broken?

Sure, this one is a bit heavy (definitely not first date material), but it can really teach you a lot about another person, as well as bring you closer together on a more meaningful level. “This is a bonding question,” Jacobs says. “It works to form a connection faster because the person will feel very seen and understood by you, and [they will] also gain insight when you answer the questions back yourself.”

23. What Is The Biggest Lesson You’ve Ever Learned?

One of the best and most attractive qualities someone can have is the ability to learn and become a better person. Someone’s answer to this question can reveal a lot about how they have grown so far in life. “This question works not only because it will get this person talking about themselves (which we all love to do), and it will also let you see how they have handled certain challenges in their life and where they want to focus their life in the future,” Schneider says.

24. What Was Your Childhood Like?

Jacobs points to this question as one that can be incredibly meaningful and help form a bond between you and your crush. Any open-ended question asking someone about their childhood will paint a picture of what sticks out to them as core memories. They might answer with specifics about their favorite TV shows as a kid, family trips they went on, their favorite home-cooked meal, or maybe even a hardship they endured as a child.

25. How Do You Feel About Me?

Come on, this is the one you really wanted to ask anyway, right? So ask it. This question will eventually be necessary to ask and get clarity, as "it is time to see if things could actually materialize with your crush," Alessandra Conti, a matchmaker at Matchmakers In The City, previously told Elite Daily.

Take inspo from these questions or copy and paste them into the chat box to spark some meaningful conversation with your crush. You’ll definitely get a stimulating chat going and gain more insight into your compatibility. And, hopefully, they’ll ask you some fun questions, too!


Perri Schneider, online dating coach

Laura Jacobs, professional matchmaker and dating coach

Dr. Joshua Klapow, clinical psychologist

Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking

Susan Winter, relationship expert

Alessandra Conti, matchmaker at Matchmakers In The City

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