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21 Questions To Ask Your Crush Over Text To Keep A Dying Conversation Going

Picture this: You're texting with someone new and the conversation is flowing. Your fingers are dancing across that little keyboard like you're some chatty Mozart. Questions to ask your crush? P'shaw, you've got those for dayz. This isn't your first texting rodeo, cowboy — but then, it happens. The dreaded text lull.

Maybe you felt it building for a while or maybe it snuck up on you, but either way, things have gone awkwardly silent. If you're like me, this is when your mind goes totally blank. What even are words, amirite? If you were to peek into my brain at this moment, you would just see a barren landscape of tumbleweeds and old boba tea straw wrappers blowing in the wind. It’s tragic.

While in the heat of the moment I go straight-up brain dead, right now — without a blank smartphone screen in front of me, staring back accusingly or a nervous system that is flooded with new-romance-hormones — I can actually come up with loads of questions to get the conversation flowing again. Twenty-one, to be exact. Keep these queries handy, so next time you can revive the chat as soon as you sense the momentum of the conversation is dying.

Keep It Light


If you are just starting to get to know each other, it’s best to keep it light and breezy. You want to ask open-ended questions that are actually fun for the recipient to think about and answer. Bonus points for making them laugh. Here are some questions to help you keep it casual.

1. If you had to choose, would you rather be sexy or smart?

2. Would you (or have you) ever gone to a nude beach?

3. If you could trade lives with any celebrity, who would it be?

4. What's your weirdest deal-breaker?

5. What’s something you find attractive that most people would consider strange?

6. What is the best present anyone has ever given you?

7. If you were suddenly invisible for the day, how would you spend it?

8. What's something everyone else loves that you think is totally overrated?

9. What's something everyone else hates that you love?

10. Do you have a nemesis? If so, who are they?

11. If you could travel through time, would you explore the past or see the future?

12. What would you do if I told you how hot you are?

Go Deeper

One of the best things about texting is that people often feel safe enough to really open up in a way that is harder face-to-face. So, once you’ve gotten through some small chit-chat, you can probably start asking some more profound questions to find out what really makes your crush tick — and figure out if they are crush-worthy at all. Here are some questions to help you dig a little deeper.

13. Would you rather have unlimited love, or unlimited money?

14. Be honest, what do you think is your worst habit?

15. If you could live anywhere in the world, where would it be?

16. What's the thing you would be most disappointed about never having gotten to experience?

17. What’s your weirdest pet peeve?

18. What’s the best advice anyone has ever given you?

19. What's the scariest thing that has ever happened to you?

20. What's the worst thing you have ever lied about, and did you get away with it?

21. What's something you are terrified to try, but you want to anyway?

Be Patient


All conversations, even digital ones, have a natural ebb and flow. So sometimes the best thing you can say is nothing at all. If you were the last one to text, kick back, relax, and give them some time to reply before firing off a bunch of questions at them. You don’t want to come off as desperate.

All of these questions are great for when you sense that the convo just needs a bit of a kickstart, but don’t be afraid to wait a bit until something comes up that would be a natural reason to reinitiate conversation.

This post was originally published on Oct. 5, 2017. It was updated on Aug. 22, 2019 by Lilli Petersen.