Having a Great Opening
Text him first to show your confidence. You might want to wait for him to text you first, but if you beat him to the punch, you can decide on the conversation and show him how confident you are. He'll be impressed—relieved that you took the pressure off for him. 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.
Mention something you've done together. Bringing up a recent conversation or activity you did together is a great, natural way to start a conversation. It can feel like you have something casual to bond over, even if you've only hung out in a group setting. Phrase it like a question so he'll be sure to respond. 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?”
Ask him a random question to show your fun side. If the guy you like has a silly side, being a little spontaneous is a great way to get his attention. Starting with a funny, random question is a surefire way to get him to respond while piquing his interest. Some possibilities include: “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??”
Give him a teasing compliment. Everyone likes an ego boost, but being too overt about it will come off as desperate. Instead, compliment the guy you like in a playful, backhanded that shows him that you're impressed, but not too impressed. Try saying something like: “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”
Send him a playful challenge. Many guys are competitive and love to be challenged. Send him a fun dare or playful request and he'll be eager to impress you and show you he can do it. You might say: “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?”
Keeping His Interest
Ask genuine questions about his interests. Think about things you know he's interested in and steer the conversation in that direction. This gives him a chance to show you who he really is, helping you connect on a deeper level. Remember to keep your tone light and playful so it doesn't feel too serious. 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 ;)” Reader Poll: We asked 179 wikiHow readers, and 59% agreed that bonding over a common interest is a great way to start a conversation with someone online. [Take Poll]
Tease him to keep him on his toes. Many guys love the chase, and throwing in some light, underhanded “insults” will make him want your approval even more. Be witty and funny to keep him interested and excited for what you'll say next. 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.
Talk to him about things you do on your own time. You want to show him that you're interested in his life, but don't make it all about him! Slip in small details about yourself to pique his interest and make him ask about you in return. 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 ;)”
Use emojis and exclamation points sparingly. Using lots of emojis and punctuation marks can come off as overly aggressive and even make you seem insecure. It's OK to throw in an emoji or exclamation mark here and there, but hold off on attaching more than one, or putting one at the end of every text. 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.
Avoid overanalyzing his short messages. When you get a short response like “k,” or even no response at all, don't panic! There are many reasons why he couldn't send a longer text, or couldn't reply at all, so stay calm. Set your phone down for a while and do something else to take your mind off of it. 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. 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.
Don't keep texting him relentlessly, especially if he's not responding. It's great that you're having fun texting with the guy you like—that means you're really connecting! Don't go overboard, though. You can come off as needy by texting him over and over again, or sending him long texts about trivial things. 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.
Be yourself when you're texting him. No matter how much you want the guy to like you back, don't try to be someone else when you're texting him. Let your natural humor, cleverness, and fun-loving personality shine through, and don't force yourself to act like someone you're not to make yourself more attractive. 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!
Leaving Him Wanting More
Wrap up the conversation when it's at a high point. Ending your conversation when it's already died down won't make the guy—or you—quite as excited about talking again. Instead, say goodbye when you're both having a great time. 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.
Use an excuse for a relaxed goodbye. Even if you don't really have to go or do anything, saying that you do is a casual, natural way out of a conversation. You won't hurt his ego by seeming like you're ditching him, and you'll also make him interested in what you're doing. Try something like: 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 ;)”
End on a question to keep him thinking about you. Say something like, “I have to go, but what do you think about…?” This is a surefire way of making him respond to you, but takes you off the hook for replying back right away. He'll be checking his phone the rest of the day to see if you've texted back! 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.”
Hint at the possibility of future plans. The best texting conversations lead to real-life ones! To solidify your chances of running into the guy in-person, hint that you might see him later or another day, but don't set anything in stone. Staying a little mysterious will make him even more excited to see you. 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 ;)”
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