Show appreciation for her interests.
Ask a question about her pop culture preferences or hobbies. Look through her Instagram feed or her profile to see what she likes. It sounds simple, but really focusing on one of her passions shows her you took the time to pay attention to what she’s into. Bonus points if you pick something other people wouldn’t normally notice or comment on. Check out these examples: “I was a midfielder. What position did you play?” “Woah, I was at that Kendrick concert, too! What do you think about the new album?” “Anime looks really cool, but I've never really gotten into it. What am I doing wrong?” “I'm also a huge Harry Potter fan. I’m guessing you’re a Hufflepuff. How close am I?”
Ask for recommendations.
Get her opinion on cool places she shows in her posts. For instance, if she has lots of photos of latte art, ask her for café recommendations. If you’ve been talking for a while (or if you’re already friends), use this strategy to easily lead into asking her on a date wherever she mentioned. Alternatively, if you’re reaching out to a stranger, just use it as a chance to kickstart a conversation and show her you want to learn more about her. “Where can I get a puppy who looks at me like that?” “So you’re a yoga pro. Best class in the city?” If you’re feeling confident when she responds, follow up with, “Want to try their Saturday class together?” Try a best of/worst of approach: “Rapid fire questions. Best sushi. Go.” or “Worst place to study. Go.”
Give her a prompt and ask her to fill in the blank.
Get her to reply by starting a little game. That way, you get to hear some of her thoughts and keep her engaged in the conversation. Just make sure the prompt you pick is fun and not anything creepy. “Fill in the blank. Together we could be experts at…” “Fill in the blank. I’ve always wanted to try…” If you’re on a dating app, you could even try: “Ok, fill in the blank. My ideal first date would be...”
Ask friendly questions about her latest posts.
When in doubt, just ask an open-ended question. Remember, you don’t have to be super clever or flirty right away—just be yourself! In fact, showing her you’re a genuine human being will probably make her like you and trust you more. You can even stand out from the crowd by including her name. “Cammie! I see you’re in Toronto right now. What have you done so far?” “How’d you learn to dance like that? I’m impressed.” Pick two things she’s done and ask her which was more fun: “Beach day vs. night out?”
Respond to her story.
Create a more natural conversation by commenting on her story. Instead of having to come up with a first message from scratch, replying to her story automatically gives you something to talk about. Keep your messages simple and authentic to make sure you don’t come across as creepy. If she posts a photo in a coffee shop, say something like, “Do you go there a lot? I’ve been looking for a new coffee shop.” If you live in the same city, try replying to her story with a recommendation like, “Woah! You’re in my neighborhood. You should check out Martin’s on Fourth.”
Compliment her sense of humor, skills, and ideas.
Use this approach instead of complimenting her looks. Separate your messages from other peoples’ DMs by responding to her funny posts or posts that show her doing something awesome. If you see a theme popping up between her posts (like a particular kind of joke or a hobby or cause she cares about), that’s a great thing to compliment her on! “Sick kickflip. Please teach me how to do that.” “Sorry, I didn’t realize I was following a professional photographer.” “That post on sea otters is 10/10. Why are they so cute?” “You have excellent taste in memes. Where do you find those?” “You’ve got better dad jokes than most dads. Does that sense of humor run in the family?”
Hint that her profile tells you something deeper about her.
Get her wondering “What do they think about me?” Send her a mysterious message that suggests she seems special or different from other people on the platform. Odds are, she’ll want to know more about what makes her stand out to you. Try these out to pique her interest: “I might be wrong, but you look like someone worth getting to know.” She’ll likely ask “why?” “From your pics, I get the feeling you would’ve made a great super spy.” “Finally, a profile I don’t find boring.”
Send her a cliffhanger message.
DM her an incomplete story that hints at something exciting. Get her guessing about what you’ll say next in order to prompt her to reply. This approach works well because you can take the second half of the sentence in any direction you want—funny, flirty, etc. “Hey, it’s Jamie. I just had the craziest thing happen…” If she asks, “What?” You can either tell her something funny or go for a smooth, flirty approach like, “The girl I have a crush on just messaged me back!” “You were at Ryan’s party last night? You must’ve left before all that chaos…” “Oh, I’ve been to that stadium, too. I made the worst mistake there…”
Bring up mutual friends.
This method works particularly well on Instagram. Check out who your mutual friends are and casually bring them up. Ask about events where you might've crossed paths. “We both know Tory and James?! Were you at their New Year’s Party?” “We have like 30 mutual friends. How have we never met?” “Nikhil told me you were pretty cool. I wanted to see if he was right.” “Cassie told me she had a friend who was a cute rugby player. Did she mean you?”
Share a post you think she’d like.
Tag her in a post, or DM the post. Pick something related to one of her interests or a post that you think matches her sense of humor. Look at her profile and/or feed to get inspiration for the type of content she likes. Pick a genuine post related to her interests. If she’s an engineer who’s really into technology, send her a post of a cool robot prototype. To tease her a little, tag her in a totally weird post. If you’re already friends and you know she’s a little clumsy, tag her in a post of a puppy trying to climb the stairs and say “Is this you?” Give her a compliment by tagging her in a post of someone famous or accomplished. If she’s into soccer, tag her in a post from a world class player and say, “Can I get your autograph before you get this famous?”
Give her a funny hypothetical scenario.
Ask her to help you with something outrageous. Pick an imaginary situation or a scene from a movie and ask her what she’d do. Try these silly, over-the-top questions to break from the normal “what’s up?” “Wanna rob a bank?” “Pretend you’re in the Lion King. What would you have done to save Mufasa?” “Okay, it’s the zombie apocalypse. What do you bring?”
Use an emoji joke or pun.
Combine emojis and text to set up a unique joke. Instead of using a cheesy one-liner, use this method to break the ice. We suggest using a cute animal emoji to keep things light. Besides, who doesn’t love a koala emoji? Send “You have all the ????-ties I’m looking for.” Use the classic line “How much does a polar ???? weigh? Enough to break the ❄️.” Send an animal emoji (ex. ????) on its own line. Then, follow up with a message that says, “Baxter! Get back here. Sorry my dog gets out sometimes. Did he bother you?” Say: “This is how I bet you spend your evenings.” Then, send your choice of funny emojis that tell a story (ex. ????????️????????????). Avoid suggestive emojis unless that’s the vibe you want to send. Caption: “This is what a first date with me would look like.” Then, tell the story of a hypothetical first date with you. For instance, ????????????????.
Send a funny GIF or meme.
Show off your personality and make her smile with a funny visual! Pick something short that doesn’t require too much effort to view. Rather than linking to a site, send the GIF or meme embedded directly in a message, so she’ll be sure to see it (and know you’re not sending her anything weird). Match her sense of humor when you can. For instance, if she posts a lot of memes, send her memes. If she sends you a GIF, send her back a GIF. For a safe choice, pick a funny animal GIF. To match her interests, reference a show, movie, or something she likes in the meme. For a bold choice, meme one of her posts with a funny caption. Avoid GIFs or memes that are mean, racist, sexist, etc.
Hint at a deeper relationship connection.
Get her interested by implying you two would be super compatible. This approach works particularly well on a dating app, rather than a general social media app. Keep in mind this sincere approach is meant to create an emotional connection. Try one of these lines to make her feel special and show you’re quality relationship material: “You look like you’d steal my favorite hoodie.” “I get the feeling we could talk for hours.” “Your profile just restored my faith in this app.”
Ask her out directly.
After you’ve sent enough messages to feel comfortable, go for it! Give her a choice of days, but let her know what type of date you’re envisioning. The advantage of asking her out directly is that you don’t have to worry about keeping her engaged through a DM conversation that might get hard to maintain. “Hey, I’d love to hear more about that. Want to discuss in person over drinks? Would Saturday or Sunday evening work better for you?” “Wanna grab coffee sometime? Friday or Saturday morning?” “Call me old fashioned, but I like to get to know people in person. Would you want to plan a beach picnic this weekend?” “You down to grab dinner together? How about Monday or Tuesday?” Being direct is the best way to quickly move from an offline to an online relationship. That way, you can see if you have that in-person chemistry.
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