101 Text Conversation Starters with a Guy (Flirty, Clever & Cute Ideas)

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Have you ever wanted to text the guy you like, but just stared blankly at the phone? Don’t worry: it happens to all of us! It’s like there are so many things you could say that you have no idea where to start. If you need some ideas for text conversation starters with a guy, we got you! Try using some of the suggestions below if you get stuck, or use them to spark your own creativity on what to text.


  • I liked the pants you were wearing the last time I saw you. They’d look good on my floor.
  • Tell me something about you that you want me to know.
  • Ask me something. Anything.
  • Hello gorgeous. What are you doing right now?
  • What would you rather do today: Keep texting back and forth? Or do something fun with me?
  • Would you let me hold your hand while we’re watching a horror movie?
  • What made you want to get to know me?
  • Send a couple of photos of sexy lingerie and ask his help choosing between them.
  • Have you ever received a really weird compliment? What was it?
  • There are squirrels mating on my balcony right now. Made me think of you.
  • Send me a song that makes you think of me?
  • Or, send him a song that makes you think of him. Like this one.
  • You look amazing today. No, I’m not stalking you—you just always look hot.
  • What would your porn name be?
  • Do you have any tattoos? Don’t tell me where they are: I want to find them myself.
  • Guess what I’m wearing right now.
  • What’s your favorite breakfast? Just so I know in advance…
  • Can you cook? Or should I send you a list of my favorite UberEats restaurants?
  • Send a picture of a sexy/romantic painting or sculpture with the caption “thinking of you”
  • What would you want to watch for a Netflix and Chill night?
  • Can you tell that I’m texting you while naked?


  • Two truths and a lie: one time I tasted dog food; I have a phobia of moths; I drool in my sleep. Guess the lie.
  • What’s the worst pick-up line you know?
  • What mythical creature is your spirit animal?
  • Tell me the weirdest thing you’ve ever eaten?
  • What’s the worst joke you know?
  • Have you been injured in a ridiculous manner? Tell me about it.
  • What do you think is the most horrible name someone could give a child?
  • If you were a type of cheese, what would it be?
  • Which actor would you want to play you in a movie about your life?
  • What’s the worst pun you know? Mine is ______.
  • Is there anything you love that other people hate, or think is weird/gross?
  • What’s the most embarrassing drink you’ve ever ordered?
  • Tell me about the most bizarre date you’ve ever had
  • Have you ever received a really horrible holiday present? What was it?
  • What’s the weirdest thing you’ve ever found in a place you’ve moved into?
  • Do you sing in the shower? If so, what do you like to sing the most?
  • What would you choose as your band name, if you had one?
  • Do you have a favorite word? Mine is _______.
  • Are there any foods you absolutely hate? I can’t stand ______.

For Deep Conversation

  • I wonder what the other versions of ourselves in alternate universes are like.
  • If you could go back in time and give your 12-year-old self one piece of advice, what would it be?
  • What podcast are you really into right now? Why?
  • Do you have a favorite book? What is it?
  • If we had a zombie apocalypse, what do you think your role would be?
  • What would you say is one of your guiltiest pleasures?
  • Is there a food or drink you’d really miss if you could never have it again?
  • Which supernatural being or thing do you wish was real?
  • What’s an unusual or outdated skill that you have (or would like to learn)?
  • Do you have a particular goal or dream that you want to achieve?
  • Are you happy with your career/job? What would be your dream job if you could have one?
  • If you could spend a few hours with anyone in history, who would it be?
  • What’s something about your culture that you absolutely love?
  • Are there any cultural things from your background/faith that you dislike or disagree with?
  • What’s the worst piece of advice anyone has ever given you?
  • Do you have any regrets? Care to share any of them?
  • What superpower do you wish you could have, and why?
  • If you could live anywhere in the world, where would you go?
  • Do you have a bucket list? If so, what are the top five items on it?
  • Are there any writers or philosophers that have really influenced you over the years?
  • Would you consider yourself religious or spiritual? If at all?
  • What kind of relationship makes you happiest/most fulfilled?
  • Do you have any dealbreakers when it comes to partners?

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  • So, sometimes I talk in my sleep and apparently it’s weird stuff like “oh, that cloud really does look like a bunny”.
  • What’s something that made you smile today?
  • Send a photo of your pet with the message “My cat/dog/ferret wants you to know that you’re missed”.
  • They say that a person’s favorite ice cream says a lot about them. Mine is _____. What do you think that means?
  • Do you have a favorite comfort food? What is it?
  • Find a ridiculously adorable meme and send it to him—see how he reacts.
  • Just so you know, I’m totally stalking your Instagram/Facebook photos right now.
  • What’s the most exciting pair of socks you own?
  • Send him a photo of you doing something fun, with “wish you were here with me!”
  • When I was a child, my favorite cartoon was ____. What was yours?
  • Pineapple on pizza? Yes or no?
  • Just so you know, my favorite thing about you is ______.
  • What would you bring on a picnic, if we had one?
  • I wish you could see how hard I smile whenever I see a message from you.
  • What pet name would you want me to use for you?
  • Do you like to dress up for Halloween?
  • What’s your favorite costume so far? (To expand upon the above)
  • Suggest playing a game together, like an online Scrabble app (or similar)
  • What are three great things that you’re grateful for today?
  • How different are you now than you were as a kid?

To Keep Him Interested

  • So, what do you want to do with me the next time we get together?
  • If I invited you to go skydiving, scuba diving, or tornado chasing, which would you choose?
  • This will probably swell your ego horribly, but I can’t stop thinking about how good you smell.
  • Once upon a time, two amazingly people met. Your turn to continue the story…
  • I’m ticklish. Want to find out where?
  • You have such an amazing back. Looking forward to wrapping my legs around it.
  • Is there a type of food you’ve always wanted to try? Want to try to cook it together?
  • Guess what I’m thinking about right now?
  • Tell me something you want to teach me.
  • I miss you. Can we fix that?
  • Secret confession: I love (strange food that you adore). Still want to keep talking to me after learning that?
  • If you don’t tell me something awful about you, I might keep thinking about you literally all the time.
  • Do you prefer baths or showers? I’m planning ahead…
  • What’s something you’ve always wanted to do? Let’s make it happen.
  • I ordered too much for dinner. Want to come over and share it?
  • Which Netflix show would you like to binge watch with me?
  • Are you adventurous? What kind of adventure would you want to go on together?
  • I want to know what you taste like.
  • Text me tomorrow morning and tell me what your dreams were like. x

As you can see, text conversation starters with a guy can range from intense and engaging to silly, fun, and delicious. Use a variety of them as you get to know your new boo, and see where your exchanges take you!

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