You don’t have to start the conversation every time, though. If you’ve started things off for your past few conversations, make him show his interest by reaching out to you this time.
If you have a class together, for example, you could make a funny comment like, “Is it just me, or was Mr. Hoffman weirder than usual in math today…” If you’ve had a memorable conversation, make it feel like an inside joke by saying something like, “OK, I still can’t get over the fact that you don’t like ice cream. How can you not like ice cream??” If you just met him at an event, like a game or a party, reference your meeting by something playful like, “Is this that guy that saved my shirt from getting a drink spilled all over it yesterday?”
“This is random but I have to know: if you could only eat one food for the rest of your life, what would it be?” “I’m having a debate with my friend and you’re the deciding vote, so no pressure, but is a hot dog technically a sandwich??”
“I heard you got the game-winning play yesterday… so I guess you’re OK at sports after all ;)” “So remember how you fixed the thermostat in my apartment yesterday? Don’t let it go to your head, but now my roommate thinks you’re some kind of handyman. LOL” “It’s cool that you got a lead role in the play and all, but don’t forget about those of us who knew you before you got famous :P”
“So I heard you’re a great cook, but I’m not sure I’ll believe it until you cook something for me. ” “Everyone says you’re a good guitar player, so maybe you should play a song for me?”
If you know he likes sports, for example, ask who his favorite teams are and how they’re doing this year. Ask how he started following them and why. You could ask about pets, favorite TV shows, classes he’s taking, and places he’s visited. Point out when you agree on something by saying, “Yeah, I feel the same!” and tease him gently when you disagree, saying, “I think you’re wrong, but I’ll forgive you for it ;)”
For example, if he’s going to play basketball with his friends, you could say something like, “Try to get the ball in the hoop this time! :P” If you’re sitting near him at lunch, you could text him later saying something like, “I saw you made your own lunch today! It even looked edible this time… ;)” Only tease him about lighter topics. Stay away from subjects like family, his appearance, politics, or other sensitive subjects, especially if you’re just getting to know him.
Showing him that you have your own life also makes you more interesting and mysterious. If he’s talking about a pet, for example, you could say, “I’ve never had a dog, I feel like I’m a cat person all the way. . . maybe I could be convinced to change my ways though ;)”
Once you get to know the guy’s texting style, you can adjust and start sending more emojis. At the start, though, play it safe and keep it simple! If you think you’re coming across as overly-enthusiastic, you probably are. Even if you’re on the fence, tone it down a little to play it safe. You can also send a funny gif or meme every once in a while, but don’t overdo it. These add-ons are funniest in smaller amounts.
Some guys tend to take longer to respond to texts, so try to adjust your expectations until you get an idea of what his typical response time is. [9] X Expert Source John KeeganDating Coach Expert Interview. 5 November 2019. Avoid asking him about it when he finally does get back to you—this can come off as desperate. You can show him that you’re relaxed and flexible by continuing the conversation as normal.
When you’re just starting to text with the guy you like, try not to send more than 2-3 texts at once without a response. If he’s not responding and you’re feeling frustrated, set your phone down and do something else for a while.
Guys are attracted to confidence, so the best thing you can do is be yourself. Remember that crafting the perfect text conversation won’t mean much if you’re totally different in person!
It might be hard to stop now when you’re enjoying the conversation, but this ensures that he’ll keep thinking about you afterward, and will already be looking forward to talking to you again. Use your instincts to tell when the time is right, like if you’ve just sent a witty text and he responded with “hahaha,” or if he just asked you an interesting question, showing that he’s engaged in the conversation.
You could say something like, “Ugh, I have to go make dinner… I guess you’ll have to wait to see what my answer is ;)” “I have to go do homework, sorry to deprive you of my amazing jokes!” “Getting in the car to drive, if you’re lucky I’ll text you when I get there ;)”
Try something like, “I have to go, but what do you think about the Lions chances this season?” or, “Ugh, I have to head out, but have you started the new season of that show yet?? It’s amazing. ”
You could say something like, “See you later. . . maybe…” or, “Maybe we’ll run into each other tomorrow ;)” To keep up your teasing tone, try something like, “I know you’re already so excited to see me in class tomorrow ;)”
