35 Questions to ask over text

Texting has become a huge part of how we connect and communicate, especially when getting to know someone new. But let’s face it—sometimes, figuring out what to say over text can be tricky. That’s where these questions to ask a guy or girl come in! Whether you’re chatting with a crush, a new friend, or someone you’re trying to get to know better, these conversation starters can help keep the energy fun, flirty, or thoughtful, depending on the vibe you’re aiming for.

From playful questions that reveal their interests and sense of humor to deeper ones that open the door for meaningful conversations, these questions are designed to break past the surface and spark engaging chats. Whether you’re looking to make someone laugh, show genuine curiosity, or subtly hint at a romantic connection, these questions will help you avoid awkward silences and keep the conversation flowing smoothly.

  1. How do you typically spend your weekends when you have free time?
  2. What’s one thing you really wish you could buy right now?
  3. What’s your favorite movie of all time, and why do you love it?
  4. What’s your favorite movie quote of all time?
  5. What’s something that doesn’t exist but you wish it were real?
  6. What’s your all-time favorite meme?
  7. What’s your go-to video or gif that never fails to crack you up?
  8. What’s an app on your phone that you think I need to check out?
  9. What’s your favorite thing—and the thing you hate most—about your phone?
  10. What website or app has had the biggest impact on your life, for better or worse?
  11. What’s your go-to snack when you’re craving something tasty?
  12. What song do you have on repeat lately?
  13. When was the last time you laughed so hard you cried?
  14. What’s the coolest “hidden gem” place or thing you’ve discovered?
  15. What’s the most embarrassing or awkward text you’ve ever accidentally sent?
  16. How many questions do you think you could answer using only pictures?
  17. What’s the weirdest or most unexpected thing that happened to you this week?
  18. What happens all the time in real life but almost never shows up in movies?
  19. What’s the coolest or most interesting thing near you right now? Snap a pic of it.
  20. What’s the best photo you’ve ever taken that you’re proud of?
  21. What’s the most ridiculous or funniest thing you’ve seen online recently?
  22. What always makes you laugh the hardest, no matter how many times you see or hear it?
  23. What’s the joke you always keep in your back pocket to make people laugh?
  24. If you could describe yourself using only three emojis, which ones would you pick?
  25. If you could live anywhere in the world, where would you set up your dream home?
  26. What’s the most ridiculous or funny item you’ve ever seen for sale online?
  27. What’s the funniest, weirdest, or most surprising text you’ve ever received?
  28. Which song has the most unforgettable intro?
  29. Do you believe in love at first sight, or do you think it’s just a myth?
  30. What’s a silly or random passion of yours that people wouldn’t expect?
  31. What’s the funniest picture you have saved on your phone?
  32. What’s the scariest item you could legally bring on a plane?
  33. Where’s your favorite spot to order takeout or get delivery from when you’re craving something good?
  34. What’s the dumbest or cheesiest pickup line you’ve heard?
  35. What’s an unwritten rule you always follow?

More Questions to Ask