Comment on his posts.
Get him to open up by asking something about his pictures and videos. Complimenting and hitting on him is a great starting point, but you can say even more to get him talking to you. When you’re looking through his profile, find a recent post the guy made and ask him something about it. Try to ask what’s happening in his picture or video to show you’re interested in his life. For example, if he posts a picture of him at the beach, you could say, “OMG, that looks so beautiful! Where is it?” As another example, if he posts a picture of him playing a board game, you could ask, “Wow, that seems really cool! Was it fun?”
Mention one of his posts in a DM.
Send him a DM if you want to keep your conversation private. Instagram comments are public, so anyone else seeing the guy’s post can read what you said. If you want to keep it low-key, share the post you like to his DMs and talk to him there instead. For example, if he posts a video of him bowling with friends, you might say, “You’ve got some serious bowling skills! What’s your highest score?” As another example, if he posts some vacation pics, you could mention, “It looks like you had such a good time on your trip! What was your favorite part?” If he posts lots of pictures of organic food, you might ask "What's your favorite organic place in the city to visit?" or "What's your favorite vegan spot?" Reader Poll: We asked 143 wikiHow readers how they initiate a conversation with a guy online, and 53% said talk about something on his profile. [Take Poll]
React to his story.
Show him you’re interested in what he’s up to with a quick reply. Tap on his profile and watch any stories he’s posted over the past day. If there’s something that intrigues you, reply to whatever he posted with a few quick comments. If he shares stories every day, try to reply to 1 or 2 every week to show him that you’re really into what he’s up to. For example, if he shares a picture of his lunch, you could say, “That sandwich looks absolutely delicious. Now I want one!” As another example, when he shares a song in his story, you could say, “That was such a bop! I can’t wait to listen to this band more!” Replying directly to his story goes right to his main inbox so he’s guaranteed to see it. If the guy doesn’t follow you back, any other DM you send goes to a separate inbox that he might not see.
Flirt with some emojis.
Emojis show him how you’re feeling without getting too wordy. You can use emojis in his DMs or directly on his posts. If you want to let him know you’re into him, you could try using “????” or “????” to make your message clear. If he posted something funny, you could always try the “????” or “????” to show him that you’re laughing. Save emojis like “????” and “❤️” for private conversations so you don’t embarrass him in the comments of his posts. Try to avoid posting a lot of emojis in a row since it can come across as a little obnoxious.
Share something he might be interested in.
Find posts he’d like to see to show him you’re paying attention. Look at the posts that you see him sharing and liking to get a sense of his interests. When you come across a post from someone else that you think he’d like, share it to his DMs and tell him it reminded you of him. That way, he’ll notice that you’ve really paid attention to him and he might continue the conversation. For example, you could share a post from a band he likes and say, “Hey, I’m not sure if you’ve seen this, but it looks like there’s a new album coming out!” As another example, if he posts about video games a lot, you could say, “Hiya, have you heard about this new game coming out? It looks SO fun!” For another example, you might share a picture of a restaurant in his area and say, “Hi! Have you seen this new place near you? It looks like they have some really good food.” If you're both into art, you could tell him about a cool exhibit that's coming up in the city.
Break the ice with a meme.
Make him laugh with a funny picture to keep your conversation light. Take a peek at his profile and posts to get an idea of what his sense of humor is like. Look for a funny image or GIF online that you have saved or from another Instagram profile to privately send him. It could be a great way to make him laugh and get the ball rolling. Instagram has a ton of meme accounts, so try searching “meme” in the search bar to see what’s really popular. A lot of messaging apps have GIFs built into the keyboard.
Send a selfie.
Drop a picture in his DMs to show him what he’s missing. If you’re feeling good about how you look, don’t be afraid to snap a quick pic and send it to his messages. You can set your pictures so he can only view them once if you want to tease him. Otherwise, you can save your pictures to the chat if you want him to be able to scroll back and see them. You could even ask how you look to make him open up more. For example, after sending a picture, you could say, “I was thinking of posting this on my profile. What do you think?” As another example, you could say, “This is my favorite outfit! How do you like it?” Avoid sending sexy pictures to your crush unless you’ve already been talking for a while and it’s consensual.
Ask him open-ended questions.
Get the guy talking with some casual Qs to learn more about him. Try to avoid asking him simple yes/no questions since it can be pretty hard keeping the conversation alive. Instead, ask him about the things he likes and let him delve deep into a topic that he’s passionate about. The guy will feel like you’re truly interested in knowing him, and he’ll keep talking if he’s interested too. Some things that you could try asking include: “What do you like to do in your free time?” “What’s your favorite memory from when you were growing up?” “How do you feel about that new Spider-Man movie coming out?”
Play a game of truth or dare.
A quick game keeps your conversation fun and flirty. Shoot the guy a message and see if he’s up for playing a game with you. Keep the topics light at first, but don’t be afraid to push him a little further as you get to know each other a little better. Start with some light questions and easy dares, and work your way up to things that are a little more flirtatious. Some fun “truth” questions you could ask could be: “What’s a secret you’ve never told anyone else?” “What’s your biggest guilty pleasure movie?” or “What’s the most embarrassing thing that’s ever happened to you?” Good dares you could try include: “Send me a selfie right now,” “Post your most embarrassing picture on Insta and leave it up for a day,” or “Tell me what we’d be doing if we were together in person right now.”
Say things you’d only bring up in person.
Saying something too direct could be a turn-off. Even though you might feel more comfortable saying things online, saying something too forward can still make someone uncomfortable. Ask yourself if you would tell him what you want to say directly to his face. If you wouldn’t feel comfortable mentioning it to him, then you should probably avoid bringing it up in his comments or DMs. Remember, even though DMs are private, he could share them somewhere else.
Avoid spamming him with messages.
A wall of messages might come across as obnoxious or intimidating. You never know if the guy you’re messaging is busy, so don’t stress out if he doesn’t reply to your messages right away. Only send 1 or 2 messages at a time and wait for the guy to reply before messaging him again. That way, it’s easier for him to catch up on the conversation and reply.
Ask to meet him IRL.
Try to set up a date to meet offline if you can. Even though it’s great to chat through Instagram, make a plan so you can see each other face to face if you live near each other. Try to build up your friendship by getting to know him more. Once you’ve built up your relationship a little bit, ask the guy if he wants to get together for a coffee or to go out on a date. For example, you could say something like, “It’s been so great chatting here, but would you want to meet up for drinks sometime soon?” As another example, you could say, “I’d love to hang out in person if you’re up for it. Do you want to grab dinner at some point?” If you live far away from the guy, you could suggest a video call or a virtual date so you can still talk to each other more.
Back off if he doesn’t respond.
If the boy hasn’t answered at all, he’s probably not interested. If he hasn’t replied to any comments or DMs you’ve sent within a day or two, ease back and give the guy some space. Stop sending him messages, leaving comments, and liking his pictures so you don’t bombard him with more notifications. Who knows, maybe he’ll notice that you’re not interacting as much and he may reach out on his own. Don’t feel discouraged if the guy you like doesn’t respond. There are other people you can try chatting with if it doesn’t work out.
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