This article was written by John Keegan
and by wikiHow staff writer, Hunter Rising
. John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.
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cited in this article, which can be found at the bottom of the page.
This article has been fact-checked, ensuring the accuracy of any cited facts and confirming the authority of its sources.
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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]
X
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.
Steps
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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] X Research source
- 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] X Research source
- Make sure to follow the guy on Instagram before you DM him. This can make him more likely to look at your message and respond.
- Reader Poll: We asked 747 wikiHow readers, and 52% of them agreed that it’s important to follow your crush on social media before you slide into their DMs. [Take Poll]
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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] X Research source
- 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?”
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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] X 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?”
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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] X Research source
- 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.
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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] X Research source
- For example, you might say, “LOL 😂 this picture really reminded me of you! Have you seen this one before?”
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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] X Research source
- 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!”
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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] X 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 😊”
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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] X Research source
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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] X Research source
- 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 😘”
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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] X Research source
- 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.
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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] X 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.
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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] X Research source
Expert Q&A
Tips
- Lead up to DMing him by following his account and liking a few of his posts so he sees your name in his notifications. [15] X Research sourceThanks
- Remember that what someone posts on their feed might not reflect their actual life. [16] X Research sourceThanks
Warnings
- Remember that anything you message a guy could be saved or shared, so think twice before sending any racy texts or pictures. [17] X Research sourceThanks
- 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] X Research sourceThanks
- 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.Thanks
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References
- ↑ https://www.psychologytoday.com/us/blog/dating-in-the-digital-age/202012/when-it-comes-relationships-is-instagram-real-life
- ↑ https://www.sweetyhigh.com/read/start-conversation-with-crush-on-instagram-tips-021419
- ↑ https://about.instagram.com/blog/announcements/introducing-photo-and-video-replies-to-stories
- ↑ https://www.seventeen.com/love/tips/g2366/flirty-texts/?slide=2
- ↑ John Keegan. Dating Coach. Expert Interview. 19 August 2021.
- ↑ https://fashionmagazine.com/wellness/how-to-slide-into-dms/
- ↑ https://droidrant.com/how-to-start-conversation-on-instagram/
- ↑ https://www.seventeen.com/love/tips/g2366/flirty-texts/?slide=19
- ↑ John Keegan. Dating Coach. Expert Interview. 19 August 2021.
- ↑ https://fashionmagazine.com/wellness/how-to-slide-into-dms/
- ↑ https://year13.com.au/articles/ways-slide-someones-dms
- ↑ https://year13.com.au/articles/ways-slide-someones-dms
- ↑ John Keegan. Dating Coach. Expert Interview. 19 August 2021.
- ↑ https://grottonetwork.com/navigate-life/relationships/things-learned-from-sliding-into-dms/
- ↑ https://www.sweetyhigh.com/read/flirt-with-crush-instagram-032018
- ↑ https://www.psychologytoday.com/us/blog/dating-in-the-digital-age/202012/when-it-comes-relationships-is-instagram-real-life
- ↑ https://kidshealth.org/en/parents/2011-sexting.html?ref=search
- ↑ https://about.instagram.com/blog/announcements/introducing-new-tools-to-protect-our-community-from-abuse