Dating
Smiling woman thinks of a deep question to ask her crush.

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

And I mean deep.

Updated: 
Originally Published: 
Constantinis/E+/Getty Images

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 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 deep questions to ask your crush 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 a guy 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. 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, the following questions 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 they enjoy doing, but you can also decide if they’re things you'd like to do as well. 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. 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? Because if it's something you can't live with, better to find this out over text rather than the hard way.

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

FatCamera/E+/Getty Images

This question to ask your crush 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?

Find out if this is an adventure 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?

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 it means for how they live their lives. 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. Is it mom? Their bestie? 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?

Aja Koska/E+/Getty Images

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? 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 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.

10. What Are Your Political Beliefs?

The idea that you shouldn’t talk about politics 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. 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, so knowing how they feel about politics 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.

12. What Do You Want In A Relationship?

Renata Angerami/E+/Getty Images

This one seems pretty obvious, but expectations about their 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.

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. 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?

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.

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.

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

Dani Ferrasanjose/Moment/Getty Images

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 and comfortable with opening up to you. You can also learn if they're an honest and open communicator — important qualities to have in any relationship.

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. 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. 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, if at all?

20. How Do You Feel About Me?

Come on, this is the one you really wanted to ask anyway, right? So ask it.

If your crush opens up and answers these questions, you're well on your way to really getting to know them on a whole new, and hopefully compatible, level.

This article was originally published on