Reference an earlier conversation.
Bring up a topic you’ve chatted about before for an easy in. If you’ve talked with the guy before, try to remember a few things from your last conversation. Mention something that you had fun talking about so you can keep the conversation light-hearted. From there, you can always move on to another topic later on. You might try saying something like: “So I finally checked out that song you recommended and it’s SO good! How did you find that band?” “Ugh, I am the worst lab partner. Do you remember what we covered in science today? “I can’t believe you said pineapple tastes good on pizza today. Are you crazy?? LOL”
Mention something he enjoys.
He’ll be excited to talk about something he’s passionate about. Pay attention to what the guy talks about during other conversations, or check his social media to see what he likes. Casually drop the topic into your chat and let him nerd out. If you seem interested in what he likes too, he’ll keep up the convo. Try texting things such as: “Have you checked out the football game yet? What team are you rooting for?” “Hey, so my friends and I are looking for board games to play. Do you have any recommendations?” “So you’re really into fishing, right? What are some of the best spots around town?” Reader Poll: We asked 143 wikiHow readers how they initiate conversations with guys online, and 53% said they talk about something on his profile. [Take Poll]
Give him a compliment.
Guys love it when you say something nice about them. You can mention something about his looks, his personality, or anything else you really like about the guy. Just avoid saying anything too forward or creepy, or else you could make him feel uncomfortable. Some things you could try include: “Seeing your smile made my day!” “Just wanted to say that your outfit was ???? today!” “You always know the perfect thing to say!”
Ask personal questions.
Learn more about him so you can build a deeper bond. Try asking about things he enjoys, his family, his career, or any other subject you think he’ll find interesting. Some questions you can try include: “What’s your favorite memory from when you were growing up?” “What are 5 things you want to do before you’re 50?” “What’s your favorite book/movie/band?”
Tell him a joke.
Now’s your chance to break the ice and show off your sense of humor. Sharing the same humor really makes a relationship stronger, so let him get to know your silly side. You can make some corny dad jokes, poke fun at something you’ve seen, or tell him anything you think he’ll find funny. Some things you might say to make him laugh include: “I had a really good joke about a balloon I wanted to tell you, but I blew it.” “Are you feeling tired? You’ve been running through my head all morning!”
Ask him for advice.
He’ll feel good knowing you respect his opinion. If you’re struggling with something or you just want an easy way to break the ice, reach out to your guy to get some help. You can get advice for anything, even if it isn’t a serious topic. Try asking for his recommendations on music, movies, or restaurants if you want to keep it light. Some things you might try texting him include: “Hey! I’m in the mood for a movie but have no idea what to watch. Do you have any reccs?” “Hi, I was wondering if I could get your help with something. Do you have a second?” “I’m SO hungry! Do you know any good restaurants around here?”
Share a funny meme or GIF.
Keep your conversation fun without even saying a word. When you see something online that makes you smile, forward it to the guy to make him laugh. It can be related to the other conversations you had or it can be a fun way to break the ice and start a new conversation on another day. For example, you might send him a picture of a cat hanging from a tree branch with the caption “Hang in there!” As another example, if you were talking about your favorite movies, you may send a GIF of your favorite scene or moment.
Tease him playfully.
A few light jabs keep the conversation from getting too serious. Teasing is a great way to poke some fun and sound a bit flirty. Only joke and tease about minor things, such as typos or small, unimportant things he says so it doesn’t feel like you’re bullying him. Emojis can help lighten the mood too. Some things you might try include: “Oh you think you can beat me in trivia, huh? Good luck ????” “You had a ‘fum’ night?? Hahaha well, I had ‘fum’ too ????”
Say something flirty.
Don’t be afraid to say something a little risqué if you like him. If the guy knows that you’re into him, he’s probably going to keep talking. Start with some small innuendos or teases so you can gauge if he’s interested in you too. Just avoid being too forward or sexual right away since you could make him feel uncomfortable. Some things you might try include: “Man, it’s so lonely over here. I wish I had someone to keep me company.” “You were in my dreams last night. Can you guess what they were about? ????” “I just miss what we could do if we were together right now…”
Send him a cute selfie.
Show off how you look to make him miss you even more. Take a couple flirty pics of yourself and choose whichever looks the most flattering. You can show off a new outfit that you look good in, or just share what you’re doing with him. He’ll just appreciate being able to see you and want to keep up the conversation. Avoid sending any nude pictures, especially if they’re unsolicited. You don’t want to risk making him feel uncomfortable or having inappropriate images spread around.
Use his name.
Guys pay attention to messages more when they see their name. Drop his name into a few messages while you’re chatting so it catches his eye. Your guy will also feel like you respect him more when he sees it. Just be careful not to use it too frequently, or it could come across as manipulative. Some things you could say are: “LOL I can’t believe you just said that, David!” “Hey Sean, can I get some advice when you have a second?” “Hi Danny! It’s been a while! How are you doing?”
Show your excitement with exclamation marks.
He’s more likely to reply if your texts sound enthusiastic. Have you ever gotten a text ending with a period and thought the person was mad at you? Use exclamation points instead to avoid confusion! Just be careful not to overdo it and sound overly excited since it won’t seem very genuine. For example, you could send: “You were so good at the concert tonight!! I couldn’t take my eyes off you!” “OMG!! I can’t believe you haven’t seen Toy Story! It’s a classic!”
End messages on a cliffhanger.
If you end the text abruptly, he’ll want to reply to learn more. If you have a crazy or funny story you want to tell the guy, don’t send it to him in one long message. Hint at what happened without actually telling him what happened instead to keep him guessing. He’ll definitely want to find out what happened, so he’s bound to ask you for more info. You could try a message like: “OMG work was absolutely insane today. I’ll have to tell you all about it.” “So I screwed up really badly in math today. You’re gonna laugh so hard at me.” “I’ve got a biiiiig secret, but I don’t know if I should tell you ????”
Say something sexy.
Turn him on so he can’t resist texting you back. If you’ve been chatting with the guy for a little while, don’t be afraid to get a little naughty when you’re messaging him. This way, he’ll know that you like him a lot more than a friend. Just be sure not to come on too strong, or else you could make him uncomfortable. Some things you might try include: “I had a pretty bad day. I know a few things you could do to make it better ????????” “I wish I could show you what I want to do to you right now…” “I just got out of the shower. Can you help me figure out what to wear?”
Propose getting together in person.
Ask if you want to meet up so you can develop a closer bond. Even though texting is a great way to catch up, it’s easier to build a stronger relationship face-to-face. See if your guy wants to hang out, get a coffee, or go out on a date. Even if you can’t meet in person, ask if he’d be up for a phone or video call instead. Some things you can try saying are: “Do you want to grab drinks tonight and finish this conversation later?” “There are so many new movies on Netflix! Wanna come over and watch one with me?” “I’ve loved chatting with you here, but I want to see you! Are you free this Friday night?”
Take breaks between texts.
Messaging him constantly makes you seem too available. Even if you’re really excited to talk with a guy, wait a little while between sending messages and replying. If you’re always messaging, he might lose interest or find it a little annoying. When you give him some space, he’ll realize how much he misses you and he’ll want to message you to keep the conversation alive.
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