Open with an intriguing question.
Texting "hey" is so basic. On the other hand, if you jump right in with an interesting question, he'll be engaged in the convo right from the start. Try a cliff-hanger so he'll want to know more. Or, if you want to get him laughing, go with something totally random! Try something like: "Did you hear what happened today?" "Want to hear a funny story?" "Would you rather be an ant or a grasshopper? Go!"
Follow up on something he mentioned before.
Show him you've been paying attention to what he said. You don't have to reinvent the wheel with every conversation—sometimes the simplest way to start chatting is to ask him about something you already talked about. As a bonus, checking back in is a subtle way to show him that you care. For instance: "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?"
Talk about whatever you have in common.
If you both like the same things, it's a built-in conversation starter. Maybe you both participate in the same activity, or you might both like the same bands or authors. Maybe you're both friends with the same people. Or, maybe you had a fun shared experience together, and something reminded you of that. Any of those things are great jumping-off points for a text, and it definitely won't seem like you're trying too hard to come up with something to talk about. Try saying: "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."
Tease him a little.
Poking a little fun could make him try harder to impress you. Think about his habits, little mistakes he's made, or a funny story you heard about him. You can even tease him about something that other people would normally compliment him on! However, don't tease him about anything he might be sensitive about, like his looks or something bad that happened. For instance, try something like: "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'!"
Give him a challenge or a dare.
Bring out his competitive side. Does he always brag about being a great cook? Or maybe his friends can't stop talking about how he's secretly an amazing drummer. Ask him to prove it to you! Not only is this a fun way to tease him a little about his talents, but it's a great excuse for the two of you to get together one-on-one. You could even send him a flirty dare to spice things up a little. 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."
Compliment him.
A little flattery is a subtle way to show someone you like them. Keep it brief and general—gushing for paragraphs about his gorgeous eyes or amazing sense of humor is definitely not casual. However, a quick little mention of it can hint that you're into him without it turning into a huge deal. For instance: "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."
Ask thoughtful questions.
Give him a chance to talk more about his interests. Asking him questions will show him that you really want to get to know him better, but it's still pretty casual. To keep it from feeling like an interrogation, try not to ask a bunch of unrelated questions in a row and share a few details about yourself. Also, ask follow-up questions about whatever he says to let him know you're really into what he's saying! 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?"
Talk about your other plans.
Make sure he knows how interesting your life is! You don't want him to think you're just sitting around waiting for him to text, so casually mention what else you're up to. That could be anything, like work, hanging out with friends, or trying out a new hobby. If he knows your schedule is packed, he'll feel lucky to be a part of your busy day. 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."
Sprinkle in emojis and gifs.
Emojis and gifs can a little flavor to your texts. It can sometimes be hard to pick up on a playful tone through text messages, but a well-timed wink emoji or dancing gif can help get your meaning across. Even an exclamation point or trailing dots can help add some nuance. Just don't overdo it—try not to add a string of emojis to the end of every text or flood his screen with gifs, for instance. 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...
Stick to light topics.
Texting isn't usually the best place for heavy conversations. For one thing, it can be hard to gauge what the other person is thinking without the benefit of seeing their facial expressions or hearing their tone of voice. That means it can be harder to know if they're feeling frustrated or even offended. Stick to lighthearted texts, and wait until you're together in person to talk about things like: Religion Finances Politics Race Health problems Relationship issues Reader Poll: We asked 328 wikiHow readers about the best ways to build a connection with someone they like over text, and only 7% of people recommended bringing up super deep, philosophical topics. [Take Poll] Instead, keep it light, fun, friendly, and sweet—save the serious topics for in-person conversation!
Match energies with him.
If he seems busy or bored, take a break from texting. Pay attention to how often he texts and how in-depth his messages are. If he's responding quickly, asking follow-up questions, or coming up with conversation topics on his own, chances are good that he's into it. On the other hand, if there are long gaps between texts and he's sending short, flat messages, save the flirting for another time when he seems more interested. 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!
Give him time to respond.
Try not to send more than 1 or 2 texts at a time. There are a lot of reasons for not responding to a text—he might have gotten busy, his phone might have died, or he may have fallen asleep, for instance. And there's definitely nothing chill about blowing up his phone with a wall of texts, so if he doesn't answer right away, take a break from the conversation. 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!
Make plans to do something low-key.
It doesn't necessarily have to be a date. Texting him about a hang-out can be a great way to move things forward without seeming like you're trying too hard. This works especially well if it's something super casual, like grabbing lunch at a new restaurant or getting together with a group of friends. You could also try something like: "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!"
Leave the conversation on a high note.
Try to cut it off just when it's getting good. Maybe he's just sent a string of cry-laughing emojis, or maybe he just finished telling you how he scored the winning goal in the state soccer championship in high school. The conversation is flowing, you're both feeling good—it might feel unnatural, but this is actually a great time to call it a day. You'll leave him wanting more, as opposed to letting the conversation wind down until neither of you can think of anything else to say. Don't end things too abruptly—wait for a natural lull, then let him know you have to go.
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