Make sure your profile reflects your personality.
Before you DM him, check out your own profile. Is your profile picture an image of you, or is it a screenshot from a cartoon? Make sure you're sharing some great photos of yourself and noting your interests on your profile so your personality shines. Share pictures that highlight your interests, like images of you roller skating, playing an instrument, or hanging out at the beach. Try not to feel pressure to look a certain way to seem appealing to him. Being proud of who you are is a super attractive quality! If you don't like having pictures of yourself online, that's okay, too. Just make sure you introduce yourself or tell him who you are when you DM him.
Check out his profile to see his interests.
Use what you learn as a conversation starter. Good topics to seek out include his favorite bands, the sports teams he supports, books he likes, and any recent trips he's taken, like a vacation at the beach or a skiing trip in the mountains. Other things to look out for include: Pictures of his pets Posts that show him playing a musical instrument Art or films he likes
Ask about something on his profile to break the ice.
Make the question genuine and specific to his interests. If he's got a bunch of pictures of himself surfing, ask what beach is featured in his photos. Perhaps his Twitter is all retweets from different musicians he likes. DM him a question about his favorite bands. He'll likely be flattered by your interest and answer! Try something like, "Hey that surfing picture is awesome! What beach is that?" or "I love Blink-182, too. What's your favorite album?" Reader Poll: We asked 146 wikiHow readers how they initiate a conversation with a guy online, and 52% said talk about something on his profile. [Take Poll]
Reference something he likes, like a TV show or a movie.
See if you can spot his favorite TV shows or movies from his profile. Send him a message with a link to a recent interview with a band that he likes. You can also send a funny meme or a GIF related to one of his favorite cartoons or movies. If you notice he's wearing a Steven Universe shirt in one of his photos, message him a GIF from the show. Caption it with, "Saw this and thought of you."
Ask him for a recommendation.
He'll likely be flattered and happy to provide one. If you're unfamiliar with a lot of things he likes, ask if he's got any suggestions for cool things to check out. This could include bands, movies, books, and even local artists worth supporting. Start by complimenting his taste to make your message friendly and flirty. Perhaps he's always referencing books that he likes. DM him something like, "I love all the books you've been posting about lately! I'm looking for new stuff to read. Do you have any recommendations?"
Bring up how you two know each other.
Talk about how you met online or in person. Be sure to include some personalized details, whether it be the messages you shared on Tinder, the funny conversation you had at a party, or the fact that you both go to the same university. If you've never met but share mutual friends or interests, reference those. If you've never met, say, "Hey my name's Sharon! We're in the same English 101 class." Maybe you met at a party and bonded over your shared interest in graphic novels. Message him, "Hey it's Rob! We met last weekend. I ended up checking out that book you recommended. It was so awesome!"
Compliment him.
A little flattery can go a long way. Message him a genuine compliment, and try to get a little deeper than just his looks. You may not know him super well, but think about what drew you to him or his profile. It could be his fashion sense, his talent for sharing hilarious memes, or his amazing art. If he's an artist, try, "I love your paintings! You use such interesting color combinations." Maybe he's always posting awesome outfit pictures. Message him, "You've got great style."
Reply to his story.
If his story piques your interest, message him about it. Better yet, ask him a question about it to boost your chances of getting a reply. Craft a message instead of simply reacting with a fire emoji. Though he may appreciate the reaction, it won't give him much to respond to. Let's say he posted a story of his cat. Message him, "Omg so cute! What's their name?" If he posted a picture of a popular bar in your city, try, "I love that place. Best patio in town!"
Keep the convo going with open-ended questions.
Build on your first message to establish a rapport. Avoid asking questions with yes or no answers, as these can make the conversation come to an end sooner. As you continue to message back and forth, respond with what comes naturally. It's totally normal to be a little nervous, but try not to take too much time thinking of the perfect response so you don't slow down the convo. For example, if you've been talking about his interest in playing guitar, ask him something like, "How did you first get into guitar?" Follow that with your own experience with guitar: "I've always wanted to play guitar, but I ended up taking piano lessons growing up instead" or "I play guitar, too. I like playing electric especially. What about you?"
Ask him to hang out in person.
This is the ultimate goal of sliding into the DMs. After sending a few messages back and forth, ask him if he would ever want to meet up in person. If you don't live in the same area, suggest that the two of you get together if you're ever in the same city. Once he says yes, give him your phone number or ask him for his to take things off social media. That way you can start texting about your fun new plans. Message him, "I really like talking to you. Would you ever want to get a drink?" You can also suggest getting dinner, seeing a movie, or hanging out at a park. If you're not in the same city, try, "Let me know if you're ever in town! I'd love to meet up and get dinner."
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