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Be confident.
If you’re going to be bold, at least be bold and sure of yourself. You’re a lot more likely to elicit a positive response if you act like you’re absolutely sure of yourself. What’s the worst that happens, she doesn’t respond? There’s no big risk here, so just give it a shot and don’t be too hesitant to strike up a conversation. Don’t be confident enough to ask for nudes or be outright sexual, though. That’s just going to come off as creepy and aggressive.
Don’t overthink it.
It’s easy to get up in your head on this one, so don’t! This isn’t a job interview, and if you don’t craft the most perfectly-worded DM of all time, it’s not the end of the world. It’s easy to talk yourself out of sending a DM, and the longer you linger on the specific language the more likely you are to forget about it. You got this, so just do it!
Try a direct approach if you're feeling bold.
For a more straightforward approach, just go for it. There’s no shame in shooting your shot and seeing what happens. Being direct about what you’re looking for is a great way to stand out from the crowd. It exudes confidence, it’s honest, and it’s sure to catch her eye. You might try something like: “Hey, you seem super cool. Want to grab a drink tonight?” “I can’t believe we go to the same school and we’ve never talked. Let’s grab some coffee some time, you seem so down to earth.” “Sorry if this is super forward, but you’re a cutie pie. Want to hang out later?”
Try a subtle approach to keep things casual at first.
If you want something a little more substantial, say hello. It’s a lot easier to connect with someone online if they know you have some shared experience or mutual friends in real life. Send her a DM by saying hello and commenting on whatever it is you have in common. Maintain a casual tone and don’t cross any lines by getting too personal or flirtatious if you aren’t ready for that. You could say, “Hey, I saw you’re friends with my buddy Jamie. Did we meet at his party last year? I’m Tony, by the way.” You might try, “You went to Clements High School? You look super familiar, were you in Mr. Grady’s homeroom?” If you don’t have anything in common, include a note on why you added her. You might say, “Hey, my name is Alex. I saw some of your posts when a friend reshared them; I love the memes you post. How are you doing?”
Share a funny meme or video.
If she shares a ton of humorous content online, connect over a joke. If she posts a funny SpongeBob Squarepants meme, like the post and then DM her another SpongeBob-related meme. If she posts a funny TikTok, send her a different funny TikTok along with a note like, “Ever see this one?” Sharing funny content is a great way to connect and get to know one another. The benefit of this move is that it’s impossible to send a mixed signal or cross a line on accident. Nobody has ever taken a funny meme the wrong way! If you want to get a little flirty with it, feel free to choose a funny meme with a bit of a flirtatious undertone.
Compliment her personality.
You can try testing your luck by sending a complimentary note. This is a good way to open the door for a more meaningful interaction. Send her a DM that’s relevant to something she posted and compliment her. Just make sure you aren’t focusing on anything physical, since it can come off the wrong way—especially if she doesn’t know you in real life. If she shares a crowdfunding campaign to help someone in need, you might send her something like, “It was really nice of you to share that fundraiser. I read through it and threw them a few bucks. What a sad story. You’re a kind soul.” If she gets into an argument with someone online, you might send her a note like, “Hey, that guy you were arguing with was being a total dork. I thought you handled that with poise.”
Ask for a recommendation.
A recommendation is a great “excuse” to message someone you don’t know. If the two of you live in the same area, ask her where she took those brunch photos at. If she posts a photo of her pet hedgehog, message her and tell her you’ve been thinking of getting a new pet and ask her some questions. You could even ask her the name of a song she posted in a video she took and shared. This is a great way to establish some rapport and connect over a shared interest. This is also a great way to connect your digital interactions to real life. If you live in the same town and you ask her for restaurant recommendations, the two of you can start talking about favorite local food joints!
Use open-ended questions and comments.
Whether it’s on her page or in the DMs, leave room for conversation. If you ever reply to her in a way where you don’t give her something to respond to, she may stop talking to you. If things feel like they’re coming to a natural close, use questions to keep things open and maintain your momentum. Stay away from one-word responses, since they can put an end to any conversation fast. For example, if she says something like, “Yeah, I work at the bowling alley over on North Avenue,” you replying with, “Oh, that’s cool!” doesn’t really give her anything to work with. However, if you said, “That’s a sweet gig. How do you like it?” or, “That’s crazy, I used to work on North Avenue too. That’s a fun area,” she’ll have something to reply to.
Keep it light and don’t be pushy.
Let your conversation develop organically and play it cool. It can take a bit of time to guide the conversation where you want it to go. Take your time and be super casual whenever the two of you interact. If the conversation comes to a natural conclusion, let it. You can always interact with her later by commenting on her posts, replying to her when she comments on your posts, or DMing her in the future. Professing any romantic interest in a stranger you meet online is rarely going to work out. It’s totally okay to have a crush, but take things super slow and don’t be overtly sexual.
Ask for her number.
If you can, move the conversation to texting. As the two of you get to know one another, aim to move from social media to the phone so that you can get to know one another even better. Don’t ask for a date right away or change your tone or anything—just casually find a way to ask for her number. If she gives it to you, start talking to her over text the same way you were over social media. You might say, “I’ve got to go to work in a bit. We can keep chatting over text if you’d like. What’s your number?” You could ask, “I’m not on Facebook Messenger all that often. My number is 555-5555 if you want to hit me up.” If she declines your offer, play it off. You might say, “No worries! I totally get it,” or, “No sweat. There’s a lot of weirdos out there, so I hear you.” You can always ask for her SnapChat if you want something a little more personal than Instagram, Facebook, or Twitter but it doesn’t feel like she’ll agree to exchange numbers.
See things from her perspective.
If she seems guarded at all, don’t take it the wrong way. Women on the internet have to put up with a lot of unfortunate nonsense. If you’re getting frustrated that she isn’t engaging or you aren’t seeing any progress here, it helps to step back and consider how she feels. Women often get a lot of unwanted advances from random guys and gals online, and it can be a lot to deal with. Be thoughtful, respect her, and let it go if you don’t get the results you want.
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