How to DM a Boy on Instagram

Written by John Keegan | Edited by Hunter Rising

Last Updated: June 20, 2022 References

If you’re crushing on a guy on Instagram, sliding into his DMs is a great way to start your conversation and get to know him even more.^{[1]
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Research source} We know there’s a lot you could say in your first message to him, but some messages will make him open up more than others. We’ve got a ton of helpful tips on what to say and example messages you can try whether you want to keep it casual or start a serious relationship!

This article is based on an interview with our professional dating coach, John Keegan, founder of The Awakened Lifestyle. Check out the full interview here.

1

Respond to his Story.

Stories are easy to respond to so you aren’t just sending a random DM. Since Instagram Stories only last for 24 hours, responding to them lets him know you’re paying attention to his posts. If you’re feeling a little nervous to break the ice, just react with an emoji or send a quick “haha” when he shares something funny. If you want to get him talking, end your message with a question to encourage him to DM you back.^{[2]
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- For example, if he posts a video of him bowling, you could say something like, “OMG I love bowling! What was your score?”
- As another example, if he posts a vacation pic, you might say, “That’s so beautiful! Where are you?”
- Accounts with a lot of followers may have their Story replies turned off.
- You can also reply to his Stories with a selfie or reaction video by tapping on the camera icon.^{[3]
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2

Mention a mutual interest.

Check his profile for an interest you share to kickstart your connection. Do your research by scrolling through his feed and finding a few things that the guy enjoys doing. When you see something that you’re into as well, slide into his DMs to talk about it. He’ll love that you can nerd out about something together and might want to keep the conversation going.^{[4]
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- For example, if you notice that he posts a lot about comic books, you could say, “You have such a Marvel-ous collection of comics, but which issue is your favorite?”
- As another example, if he posts about a football game, you might send, “That was such a crazy game last night! Wasn’t that overtime play insane?”

3

Ask him for recommendations.

You can casually sneak into his DMs and start chatting by getting his help. Read the guy’s Insta bio and scroll through his posts to get an idea of the things he likes. If you’re interested in something he shares, reference it in a message and ask him something about it. He’ll love to talk about his hobbies and be happy to share more info with you.^{[5]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.}
- For example, if you notice that he posts a lot about shoes, you could say, “Are those vintage Jordans in your last post? I’ve been looking for a pair for soo long, do you know where I can find some?”
- As another example, if he posts about books that he’s read, you could ask, “Hey! I notice that you read a TON and I’ve been trying to get into more sci-fi lately. Are there any authors that I should check out?”

4

Pose an open-ended question.

Ask him about his life and hobbies to get him to open up. Open-ended questions can't be answered with one-word replies, so they make great conversation starters. Start your question with “what,” “how,” or “why” to help get him talking. You could ask him about his hobbies, something about his childhood, or talk about something you saw in his posts. Just stay away from questions that are too personal since it could make him uncomfortable.^{[6]
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- For example, you could ask, “There have been so many good movies this year. What’s your top ten list?”
- As another example, you could ask, “What’s your favorite memory from growing up?”
- Remember to keep up your side of the conversation too! You should give your own answer to the question after he responds so the guy can learn more about you too.

5

Share a funny meme.

A relatable meme breaks the ice without a lot of pressure. You can usually get an idea of the guy’s sense of humor from his Stories and the rest of the posts on his profile. Search online or on another Instagram meme page for something that you think will make him laugh and send it his way. Send a quick follow-up message to give him more to respond to.^{[7]
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- For example, you might say, “LOL 😂 this picture really reminded me of you! Have you seen this one before?”

6

Tell him a cheesy joke.

Making him laugh shows off your great sense of humor. Even a silly dad joke can be enough to make someone laugh. Look up some good potential one-liners that you think are funny and try using your favorite to break the ice in a DM. If he thinks you’re funny, he’ll probably laugh and respond so you can keep chatting.^{[8]
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- For example, you could say, “This might sound cheesy, but you’ve stolen a pizza my heart! 😂🍕”
- As another example, you could say, “Knock knock.” When they ask who’s there, say, “Ivana.” When they ask Ivana who, you might say, “Ivana get to know you better, so hello!”

7

Send him a picture or video.

Show him what he’s missing to make him want more. Snap a quick selfie or picture of whatever you’re doing and drop it in his DMs. Send a quick message or question with your picture so he has something more to respond to. Just avoid sending any nude or sexual pictures out of the blue since they could make him uncomfortable or they could get shared around.^{[9]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.}
- For example, you could send a selfie and ask, “New outfit, what do you think?”
- As another example, you could say something like, “Check out this sunset! Wish you could watch it with me 😊”

8

Stick to light topics to keep it casual.

Serious or taboo subjects might turn him off right away. DMing a guy should be fun as you get to know him more, so try to stay away from any topics like politics or religion. Keep your DMs free from any drama by talking about your hobbies and things that you both enjoy so you don’t make the guy feel uncomfortable.^{[10]
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9

Offer him a flirty compliment.

Saying something cute lets him know you want more than a friendship. If you’re crushing on the guy you’re DMing, show him that you want to take your relationship to the next level. Say something that’s light and fun without being too sexual right away. Throw in a few emojis so your DMs sound a little flirtier, but don’t go too overboard.^{[11]
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- For example, you could say something like, “Your outfit looked 🔥🔥🔥 in your last post! Wish I was there with you 😉”
- As another example, you might say, “📗📘📙📕 all these library books but here I am checking YOU out 😘”

10

Ask him out if you’re feeling bold.

Let him know your intentions clearly so he doesn’t get mixed messages. Take a little time to message the guy back and forth to see if you have a good connection. If you’re really into him, be direct and see if he’s interested in getting together in person some time. You could ask him to get a coffee or meet up at the mall to go out on a date.^{[12]
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- For example, you could say something like, “It’s been so fun chatting with you here, but I’d love to meet up soon. Do you want to go to a cafe this Saturday?”
- As another example, you could say, “If you want to see some beautiful art, I know a great museum that’s nearby. Do you want to go with me this weekend?”
- If the guy lives far away, ask if he wants to do a video call or virtual date instead.

11

Let him respond before messaging him again.

Sending a lot of DMs could seem a little clingy. Even though you might be really eager to talk with the guy, he might be intimidated if he sees a wall of texts from you. Only send him one message at a time and give him a chance to read and reply to it when he gets the chance.^{[13]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.}
- Find something fun to do while you’re waiting so you don’t stress out thinking about his reply.
- Rather than replying to his DMs right away, try matching his texting speed. If he took a few hours to reply, then you can wait a few hours to reply too. That way, it doesn’t seem like you were waiting for his text.

12

Move on if you’re left on read.

He might not be interested if he stops replying. We know that it’s never fun when a guy stops chatting with you, but don’t get discouraged. Rather than holding on and trying to convince the guy to chat with you, look for someone new. There are probably a lot of other boys on Instagram that are excited to talk with you, so slide into their DMs and see how they respond.^{[14]
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Warnings

Remember that anything you message a guy could be saved or shared, so think twice before sending any racy texts or pictures.^{[17]
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If you don’t follow each other on Instagram, your DMs could go to a separate “Message Requests” inbox where the guy might not see them.^{[18]
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Celebrities and other Instagram accounts with over 75,000 followers probably won’t see your messages since a lot of people try to reach out to them.^{[19]
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