“Did you hear what happened today?” “Want to hear a funny story?” “Would you rather be an ant or a grasshopper? Go!”
“Hey I remember you said you weren’t feeling well. Are you doing better?” “How did you do on the SATs last weekend?” “Did you have fun on your fishing trip?”
“I can’t believe we won at the very last second! Go CAVS!” “I just snagged a vintage David Bowie vinyl at a ridiculous bargain. Listen party at my place?” “Hey I haven’t seen James in a while but I heard he’s graduating tomorrow! Are you guys still close?” “We have to get lunch at that food truck again! I passed by there today and immediately started craving another one of those wraps. "
“I heard you ate 10 pieces of pizza at Carlos’ house last weekend. I won’t be able to afford to pick up the check on our first date!” “See you at the party tomorrow—as long as you don’t get lost on the way there again!” “I gotta go study for the math test tomorrow. I guess you can just relax all night though, Mr. ‘I get an A every week’!”
You could say, “I keep hearing you’re an epic gamer, but idk. I think we need to face off on Mortal Kombat. " Or you might say something like, “I dare you to only speak in questions tomorrow. But you have to play it off so nobody knows it. "
“I loved the shirt you wore today. Is it new?” “You’re probably the funniest person I know. " “No wonder everybody loves you!” “You’re really fun to talk to. "
For instance, if you ask about his day and he says he was playing soccer, you might say, “Are you on a team or do you just play with friends?” If he mentions that he ate at a certain restaurant, you could say, “I’ve never been there but I’ve been wanting to try it! What do you recommend on the menu?” Try learning more about his interests by saying something like, “I don’t know much about rock climbing but it seems fun. How did you get into it?”
For instance, you might wrap up a conversation by saying something like, “Gotta run, my friend Jonah is having a Masked Singer watch party! You should come sometime!” Or, you might tell him how much fun you had on your trip to the beach last weekend. It doesn’t have to be super specific—you could say, “If you want to hang out Saturday I have some free time in the afternoon. "
Let him know you’re joking with playful emojis like 😂 or 😉. Show you’re embarrassed with 🤦♀️. Get casually flirty with 😘 or 😍. Use your favorite gif to show you’re embarrassed, laughing, gloating, being sneaky, or having a great time. Hint at more by trailing off your punctuation. . .
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If he’s always like that when you text, but he’s fun and engaging when you’re with him in person, he might just dislike texting!
If he never answers back, give it a few days, then strike up a new conversation. If he doesn’t respond to that either, work on finding a new cutie to text!
“Hey can you swing by after work tomorrow? I need your advice on something. " “I just interviewed for a job near your building and it went well! Let’s meet up so you can show me the best places to eat. " “Come over and watch the game tomorrow? My roommate will have a few friends over. There will be wings!”
Don’t end things too abruptly—wait for a natural lull, then let him know you have to go.
