91+ Flirty Truth or Dare Questions Over Text (for Him)

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By jones


Ever thought of spicing up your texting game? Dive into the digital twist on the age-old truth or dare, perfect for some undercover flirting with that dude you’ve been eyeing.

Discover shared quirks and get that bond growing!

91 Sassy Truth or Dare Text Challenges

mtv truth GIF

Starting a chat with your latest crush? Truth questions are like your secret handshake. They pave the way for that fun, flirty convos that might just roll into your next coffee date.

And hey, if you’re feeling a tad bold, these prompts can be your sly way of letting him in on your little secret. Yep, that you’re kinda into him. Wink, wink.

Got a list here of over 100 cheeky, giggle-worthy, and oh-so-red-face truth or dare texts.

They’re your ticket to leveling up in the relationship game.

And the best part? You can shoot these challenges across any platform – be it

  1. texting,
  2. Facebook,
  3. Snapchat,
  4. Skype,
  5. or even Facetime. Your pick!

How to Play Truth or Dare Over Text/Chatting.

Lucy Hale GIF by Truth or Dare

Ever played truth or dare in the digital age? Here’s the twist: since it’s not an in-person gig, every dare needs some legit proof. Snap a pic, shoot a video, or drop a voice note, depending on the challenge.

Not vibing with the dare? No sweat! Swap it out for another. But remember, the second one’s a keeper, no take-backs.

Buckle up, and let’s dive in. Bet these will tickle your fancy!

The text every guy is dying to get
Send these simple but powerful text messages to a man to make him fall in love and commit to you! (how-to video)

91 Flirty & Embarrassing Truth Or Dares to Text Your Crush/Boyfriend.

Dive into a game that’s all about bonding, goofing around, unveiling mysteries, and pure, unadulterated fun.

And hey, why not throw these dares at your boyfriend too😉? A little playful challenge never hurt anyone, right?

Kicking things off with some truth?

After all, they say it’s the key to breaking those single shackles. Let’s roll!

👉 Read     Does he like me more than a friend(10 Signs he Does!)

45 Funny/Embarrassing DARES for Text

  1. Text your best friend and say, “I know your secret.”
  2. Change your profile picture to a clown for an hour.
  3. Wear socks on your hands for the next 10 texts.
  4. Call the third contact on your phone and sing “Happy Birthday,” even if it’s not their birthday.
  5. Text a random number, “Do you believe in aliens?”
  6. Wear all your clothes inside out and send a pic.
  7. Try to do the moonwalk and record it.
  8. Eat a spoonful of mustard and film your reaction.
  9. Wear your shoes on the wrong feet for an hour.
  10. 👉 Read  9 Flirty Text Messages To Make Him Want You Even More
  11. Text your mom and ask her how to boil water.
  12. Draw a face on your belly and make it talk in a video.
  13. Use a beauty filter and send the most glamorous selfie.
  14. Call a pizza place and ask if they sell burgers.
  15. Text your crush and say, “Ever thought of us as Batman and Robin?”
  16. Wear underwear on your head and strike a superhero pose.
  17. Try to touch your nose with your tongue.
  18. Send a voice note saying, “I’m a teapot, short and stout.”
  19. Pretend you’re a chicken in a video clip.
  20. Send a text using only emojis.
  21. Put on as many shirts as you can and send a photo.
  22. Call a friend and talk in an alien language.
  23. Text someone, “Is your refrigerator running?”
  24. Wear glasses upside down and send a snap.
  25. Pretend you’re underwater in a video.
  26. Send a dramatic selfie with the caption, “Mondays, am I right?”
  27. Text a joke to the last person you called.
  28. Pretend you’re a cat and send a voice note of your best “meow.”
  29. Call a friend and convince them it’s their future self-calling.
  30. Send a pic of the weirdest item in your room.
  31. Text, “Why did the chicken cross the road?” to a random contact.
  32. Wear a towel as a cape and send a pic.
  33. Send a voice note of your most dramatic evil laugh.
  34. Text a friend, “I can’t find my phone, can you call it?”
  35. Pretend you’re a DJ and send a clip of your best “mix.”
  36. Wear your pants as a shirt and send a photo.
  37. Call a random contact and ask if they’ve seen your imaginary pet snake.
  38. Send a pic of you trying to balance a spoon on your nose.
  39. Text a friend, “Did you just wink at me?”
  40. Pretend you’re in a silent movie and send a clip.
  41. Send a pic of you doing your best ballet pose.
  42. Text a friend, “I dreamt you stole my pizza last night.”
  43. Send a voice note of you yodeling.
  44. Wear gloves on your feet and send a pic.
  45. Text a friend, “Do you think I’d make a good astronaut?”
  46. Send a pic of you with socks on your ears.

Flirty TRUTH Questions Over Text.

Dive into these thoughtfully curated questions below, perfect for delving deeper into his world.

Not only will they offer a glimpse into his soul, but they’ll also pave the way for you to become that trusted ally he leans on.

It’s like laying the first brick for a relationship built to last.

The 10 second text that will make him smile for hours.

  1. What’s the most daring thing you’ve ever done on a date?
  2. When was the last time you got really angry?
  3. Have you ever sent a text to the wrong person by mistake?
  4. What’s something you can’t have your mom find out about?
  5. Do you have any secret talents?
  6. Do you have a name for your special places?
  7. What’s the most flirtatious thing you’ve ever done?
  8. Have you ever flashed someone?
  9. How many women have you kissed?
  10. What’s a secret you’ve never told anyone because it’s too embarrassing?
  11. What’s the most embarrassing thing you did while drunk? Describe in detail.
  12. Who is the one person you most regret kissing?
  13. Have you ever had a crush on a friend’s partner?
  14. What’s the longest you’ve gone without a shower?
  15. Have you ever stalked someone on Facebook?
  16. What’s the most childish thing you still do?
  17. What’s the worst gift you’ve ever gotten?
  18. Have you ever shared a toothbrush with anyone?
  19. What’s the biggest lie you’ve ever told?
  20. Have you ever cheated on a test?
  21. What’s the most scandalous outfit you’ve ever worn?
  22. Who’s the last person you stalked on social media?
  23. Have you ever had a dream about someone you know?
  24. What’s the longest you’ve ever slept?
  25. Have you ever lied about your age?
  26. What’s the most ridiculous thing you’ve ever done to get someone’s attention?
  27. Have you ever been caught checking someone out?
  28. What’s the most embarrassing song on your playlist?
  29. Have you ever pretended to be someone else while texting?
  30. What’s the silliest thing you’ve ever lied about?
  31. Have you ever danced on a table or bar?
  32. What’s something you’ve done that you hope your parents never find out about?
  33. Have you ever had a crush on a teacher or boss?
Has a guy ever ignored your texts? Discover the secret “Attention Text” that makes a man think about you nonstop… to the point of pure obsession – in Amy North’s how-to video! 😍
  1. What’s the most embarrassing thing in your search history?
  2. Have you ever accidentally sent an inappropriate text to your family or work group chat?
  3. What’s the most embarrassing nickname you’ve ever had?
  4. Have you ever pretended to like something to impress a crush?
  5. What’s the most awkward situation you’ve ever been in with a crush?
  6. Have you ever been caught doing something you shouldn’t have been doing?
  7. What’s the most flirtatious thing you’ve done when you thought no one was looking?
  8. Have you ever had a wardrobe malfunction?
  9. What’s the most embarrassing thing you’ve said in front of someone you like?
  10. Have you ever been rejected and how did you handle it?
  11. What’s the most ridiculous thing you’ve done because of a dare?
  12. Have you ever sent a flirty text to the wrong person?
  13. What’s the most embarrassing photo of you?



Dive into these 82 truth-or-dare prompts, and you’re in for a rollercoaster of fun, flirty vibes, and a whole lot of chuckles.

These truth bombs might just reveal tidbits about him that’ll have you thinking, “Did I really want to know that?” 😄

As for the dares? Well, they’re a recipe for side-splitting laughter and, who knows, maybe a sneak peek of him in his skivvies.

Dive in, have a blast, and circle back with the juicy details.

Ever stumbled upon a revelation that left you gobsmacked? Or watched him do the quirkiest dare? Do tell!

Cheers to the fun times ahead,