Want to chat with the guy you like on Instagram but unsure how to begin? Instagram isn’t just for sharing your best photos and videos—it’s also a fantastic platform to connect with someone you’re interested in. There are plenty of ways to stay in touch with him on the app, and even a few short direct messages can leave a lasting impression. This article is packed with examples to help you start a conversation and get to know the guy you like better!
Steps
Comment on his posts.

Start a conversation by asking something about the photos or videos he posts. Complimenting and flirting with him is a great starting point, but you can go further to keep him engaged. As you browse his profile, find his most recent post and ask a question about it. Look for something in the photo or video to inquire about; this will show him you’re genuinely interested in his life.
- For example, if he posts a picture of himself at the beach, you could say, “Wow, this looks amazing! Where is this?”
- Another example: if he shares a photo of himself playing board games, you might ask, “This looks fun! Is it a good game?”
Mention one of his posts in a direct message.

Send him a direct message if you want to chat privately. Instagram comments are public, so anyone who views his post can see your comments. If you prefer to keep things more personal, you can share the post you like in his direct messages and ask your questions there.
- For example, if he posts a video of himself bowling with friends, you could say, “Your bowling technique looks so professional! What’s your highest score?”
- Another example: if he shares vacation photos, you might say, “Looks like you had a great trip! What was your favorite part?”
- If he posts a lot about organic food, you could ask, “Where do you usually shop for organic food?” or “What’s your favorite vegan restaurant?”
Respond to his story.

Show him you’re interested in his life by responding quickly. Tap on his profile and check out the stories he posted recently. If something catches your eye, reply with a short comment. If he shares stories daily, try to respond once or twice a week to show genuine interest.
- For example, if he shares a photo of his lunch, you could say, “That sandwich looks amazing. I’m so hungry now!”
- Another example: if he shares a song on his story, you might say, “This track sounds awesome! I’d love to hear more!”
- Story replies go straight to his main inbox, so he’ll definitely see them. If he doesn’t follow you back, your direct messages might end up in a separate folder he doesn’t check often.
Flirt with emojis.

Emojis can convey your feelings without needing lengthy explanations. You can use emojis in direct messages or directly on his posts. If you want to express affection, try using “🔥” or “😍” to make your message clear. If he posts something funny, you can respond with “😂” or “😆” to show you’re laughing.
- Save emojis like “😘” and “❤️” for private conversations to avoid making him feel awkward in public comment sections.
- Avoid spamming too many emojis in a row to prevent coming across as overwhelming.
Share something he might be interested in.

Find posts he enjoys to show you’re paying attention to his interests. Check out the posts he shares and likes to understand what he’s into. When you come across a post you think he’d like, share it in his direct messages and mention how it reminded you of him. This will show him you genuinely care and encourage him to keep the conversation going.
- For example, you could share a post from a band he likes and say, “Not sure if you’ve seen this, but it looks like they just dropped a new album!”
- If he posts a lot about video games, you might say, “Have you heard about the new game release? It looks so fun!”
- Another example: share a photo of a restaurant near his area and say, “Have you checked out this new spot? Their menu looks amazing!”
- If you both enjoy art, let him know about an upcoming exhibition in the city.
Break the ice with a meme.

Make him laugh with a funny image to keep the conversation lighthearted. Glance through his profile and posts to get a sense of his humor. Find a meme or GIF online, either from your saved collection or another Instagram account, and send it directly to him. This can be a great way to grab his attention and start a fun conversation.
- Instagram has countless meme accounts. Search “meme” in the search bar to see what’s trending.
- Many messaging apps have GIF keyboards built in.
Send a selfie.

Send him a photo in a direct message to show him what he’s missing out on. If you’re feeling confident about your look, don’t hesitate to snap a quick picture and send it his way. You can set it so he only sees the photo once for a playful tease or keep it in the chat if you want him to revisit it. You could even ask for his opinion to make him feel more involved.
- For example, after sending a photo, you might say, “Thinking of posting this on my profile. What do you think?”
- Another example: “This is my favorite outfit! How does it look?”
- Avoid sending provocative photos to someone you’re crushing on unless you’ve been talking for a while and both are comfortable with it.
Ask him open-ended questions.

Encourage him to open up with casual questions to learn more about him. Avoid yes-or-no questions, as they can make it harder to keep the conversation flowing. Instead, ask about his interests and encourage him to elaborate on topics he’s passionate about. He’ll feel that you genuinely want to know him better and will keep the conversation going if he’s interested too. You could ask things like:
- “What do you enjoy doing in your free time?”
- “What’s your happiest childhood memory?”
- “What did you think of the new Spider-Man movie?”
Play truth or dare.

A quick game can add a fun and flirty twist to your conversation. Send him a message asking if he’d like to play with you. Start with lighthearted topics, but don’t shy away from getting a little bolder as you grow closer. Begin with simple questions and easy challenges, gradually adding a touch of romance.
- Some “truth” questions you could ask include: “What’s a secret you’ve never told anyone?”, “What’s a movie everyone hates but you love?”, or “What’s the most embarrassing thing that’s ever happened to you?”
- Fun dares to try might be: “Send me a selfie right now,” “Post your most embarrassing photo on Instagram and leave it up for a day,” or “Tell me what we’d do if we met up right now.”
Only write what you’d say in person.

Overly bold statements can sometimes come off as uncomfortable. Even if you feel more at ease chatting online, saying something too forward might still make the other person uneasy. Ask yourself if you’d say it to his face. If not, avoid commenting on his posts or sending it in a direct message.
- Remember, even though direct messages are private, he could still share them elsewhere.
Avoid spamming messages.

A barrage of back-to-back messages can feel overwhelming or annoying. You don’t know if the guy you’re messaging is busy, so don’t stress if he doesn’t reply right away. Limit yourself to 1-2 messages at a time and wait for him to respond before sending more. This way, he can easily keep up with the conversation and reply.
Suggest meeting him in person.

Try to arrange an in-person date if possible. While chatting on Instagram is fun, you should plan to meet face-to-face if you’re not too far apart. Build your friendship by getting to know him better. Once your connection feels stronger, ask him if he’d like to grab coffee or go on a date with you.
- For example, you could say, “I’ve really enjoyed chatting with you. Would you like to meet up for a drink sometime?”
- Another example: “How about we go out for dinner one of these days?”
- If you live far apart, suggest a video call or a virtual date to spend more time together.
Step back if he doesn’t respond.

If he doesn’t reply to any of your messages, he might not be interested. If he hasn’t responded to your comments or direct messages for a day or two, it’s best to give him some space. Avoid sending more messages, commenting, or liking his photos. Who knows? He might reach out if he notices you’ve stopped engaging.
- Don’t feel bad if he doesn’t respond. There are plenty of other people you can connect with besides him.
Tips
- Try sending messages at times when he’s likely to respond. A message at 3 a.m. has a lower chance of getting a reply compared to one sent at 6 p.m.
Warnings
- Avoid sexting or bringing up anything overly suggestive if you’ve just started talking, as it might make him uncomfortable.
