It can be hard to hit the right note when you're texting a new special someone, so having some questions to ask your crush can help you steer the conversation in the right direction and encourage them to open up. It saves you the trouble of having to come up with a constant stream of witty texts, and it basically guarantees that someone is going to be excited to talk to you. Pretty much everybody loves talking about themselves.
But you know who else asks a lot of questions? Interviewers. So when you're thinking of questions to text your crush, keep it as personal as possible — in other words, no generic questions about where they see themselves in five years. There’s plenty of time to get into more serious conversations about your future later on, and it will be so much more meaningful when you aren't just texting. Trust me.
Try to stick to open-ended, thought-provoking questions. (Really, there are only so many answers to “wyd.”) Courtney Tracy, LCSW, PsyD, therapist and relationship expert, told Women’s Health, “Open-ended questions allow the other person to express their true, authentic self. It’s a good way to get a sense of who the person really is.”
That said, if you feel like you are doing all of the legwork in keeping a text conversation going, then cut yourself some slack. It takes two people to have a flowing conversation, and not all of the pressure should be on you to make your connection jive via text.
Here are some questions to text your crush while texting to find out whether you two have the chemistry to make your connection last:
1. When Was The Last Time You Cried?
You don't need them to tell you why they cried, just find out whether they can keep up with your weekly regimen (or if they haven’t cried since approximately half an eon ago).
2. What Were You Like When You Were A Kid?
Talking about what enormous dorks you both were works 99% of the time.
3. What's The Weirdest Pet You Would Like To Have?
Forget snakes. Let's talk about how you fantasize about owning a leech.
4. What's Your Biggest Deal-Breaker On A Date?
Let’s get this out of the way — if you two are totally incompatible, wouldn’t you rather know now?
5. What Color Is Your Aura?
Bonus points if they not only know the color but also have some idea about which chakra it's closest to.
6. What’s The Best Meal You’ve Ever Had?
Mine is a sandwich in Venice that I had in 2018.
7. What's Your Opinion On Free Will?
The perfect question for philosophy students and astrology lovers alike.
8. What's The Best Compliment You've Ever Received?
Once you know the competition, you'll have some idea of how to beat it. Because nobody compliments like you compliment.
9. How Would You Fare During The End Of The World?
With the end of days looming nigh and whatnot, it's probably a good idea to figure out of if this is someone who would learn to till the land... or if they would eat you first.
10. Would You Rather Live In The City Or In The Woods?
My parents are woods people. I grew up in the woods. I need to be with someone who is city all the way.
11. Do You Believe In Soulmates?
I don't know if I believe in soulmates, or if I just want to believe in them..
12. What Are You Most Afraid Of?
Recurring nightmares, childhood terrors, and similar subjects naturally follow asking your crush this question.
13. Have You Ever Fallen In Love With Your Best Friend?
It’s a good idea to have this question answered early on, especially if you’re worried there are any lingering feelings there.
14. How Many People Are You Crushing On Right Now?
Don't be too disappointed if you're talking to someone who has five different crushes a day. Crushes are fun! And it doesn't mean they're not into you.
15. What's The Worst Job You've Ever Had?
Sometimes, complaining = bonding.
16. Who Do You Talk To When You're Feeling Sad?
Everyone needs a friend to text 20 times in a row while panicking and then follow up four hours later with a casual "...but how r u??"
17. Who Was Your First Crush?
You know how crushes flirt with one another? By talking about their previous crushes.
18. Do You Eat Things That Have Been Dropped On The Floor?
Making sure you’re on the same page about the 10-second rule is key.
19. What's The One Thing You Would Save From Your Burning House?
I mean, after their pets. Always pets first.
20. Are You Ticklish?
If you're hoping your bodies will get close sooner rather than later, this is definitely the question to find out whether it's on.
21. What Was Your Favorite Movie Growing Up?
Learning about your crush’s current likes and interests is important, but finding out what they were into growing up can give you even more insight into who they are.
22. If You Could Pick A Superpower, What Would You Choose?
I love this question because it gives you some insight into what your crush values most. Not to mention, it can lead to a fun debate between flying and invisibility.
23. What’s Your Dorkiest Habit?
When you’re starting to see someone new, it’s easy to have on rose-colored classes. Learning about your crush’s habits — especially the dorky ones — can help keep you grounded. Plus, it opens up the floor for you to tell them about yourself more, too.
24. Do You Have Any Guilty Pleasures?
Be warned: This question could steer the conversation in a steamier direction.
25. Are You Into Astrology?
If you aren’t comparing charts, are you really into each other? In all seriousness, this can be a fun way to get to know your crush a little more — even if you don’t buy into astrology, it’s an easy conversation starter.
26. What Drives You? What Is Your Passion?
Learning what makes someone tick is the quickest way to see what life with them might be like.
27. What Is Your Most Embarrassing Moment?
Mine was when a guy saw my vision board and realized all the men on it looked like him. Embarrassing? Yes. Did the board work, therefore solidifying my belief law of attraction? Also yes.
28. What Would You Consider A Perfect Day?
One person’s ideal day is running a marathon. Another person’s may be waking up at noon and marathon watching Emily in Paris. Might as well figure that out now.
29. What Is The Best Meal You’ve Ever Had?
If it doesn’t involve cheese, chocolate, or chili peppers, I’m not interested.
30. What Is The Best Gift You’ve Ever Bought Yourself?
It’s a low-key way to figure out if they have good taste for your future presents.
31. Who Is Your Celebrity Crush?
Are their tastes diverse? Or are they more of a one-type kind of person? As a South-Asian woman often mistaken for being Latina, this helps me deduce if I’m checking off their Latinx fetish box or if they are genuinely interested in me.
32. Who Is Your Favorite Musician?
Sorry, but if you say Neil Diamond, it’s never going to work.
33. What Do You Like Most About Yourself?
Confidence (not cockiness) goes a long way. If a person can be honest about their favorite traits without sounding full of themselves, that’s a good start.
34. How Many Times Have You Been In Love?
My ex had been in love so many times, I began to suspect he would have fallen in love with anyone. I’m pretty sure I could have been a cardboard cutout and he would have still proposed.
35. What Made You Swipe Right?
Tell me why you like me please! And not just because my boobs look good in this dress.
36. What Do You Like To Do For Fun?
If they say foraging for berries, the answer is immediately no. And yes, someone did say that to me once. Of course, if you’re into foraging berries let me know because I have a really cute guy for you. I’m more of a buy berries at the store kind of gal.
37. What Is Your Proudest Accomplishment?
This question gives you a chance to see what they hold dear. Is it their tower of Cheetos? Or the book they wrote? Personally, I’d like someone who values both.
38. Have You Been To Therapy?
Therapy, healing past trauma, and mediation is my jam. Being with someone who is into all of that, as well, helps me know we’re on the same page.
39. What’s Your Ideal Vacation?
I love hiking and sightseeing, but if we’re talking ideal, I’m going with the beach. No other answers accepted.
40. What’s On Your Bucket List?
One person’s bucket list is another person’s worst nightmare. Let’s clear this up right away.
No matter what question (or questions) you decide to send, keep in mind that you can always use the same questions to text your crush for the next time you see them in person. A textual flirtation can be fun, but an IRL relationship is so much better.
Courtney Tracy, LCSW, PsyD, therapist, and relationship expert
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