Have a crush in school but too shy to ask her out in person? Chanced upon someone’s Instagram account but don’t know how to ask him out on a date without sounding like another weirdo off the net? Let us be your wingman. Here’s a collation of 9 perfectly non-creepy ways to approach your crush via social media. 

#1 Dedicate a song

Credit: Giphy

Who doesn’t love to be serenaded by someone through a song? It’s a classic. But of course, we’re not talking about that boombox holding outside your crush’s bedroom ala 1989 classic, Say Anything — you can always upload a video of yourself singing a cover of your crush’s favourite song or a song with all the right lyrics on Instagram or Facebook, dedicated to him/her. At the end of the video, remember to pop the question with a charming smile! 

#2 Keep it real

Credit: Bustle

No tacky tricks or try-hard pickup lines here. Treat your crush like a regular human being and converse normally! Tell her you love her witty tweets or tell him it’s really cool he does (one of his interests based on his Instagram) and would love to have coffee sometime! Simple as that. Be honest and genuine — and if it doesn’t work out, you might just end up making a new friend! 

#3 Be the online confidante 

Care for your crush subtly through comforting replies to their troubled Instagram captions (if any) or wish them luck on a major presentation they tweeted about, or even just wishing them a nice day. Make sure to leave a deep, good impression before sliding into their PM and suggest continuing the conversation in person. Take it slow and make sure they reply to your tweets/comments before direct-messaging them. Of course, don’t start leaving a message on every single post they make – keep your responses sporadic, nonchalant and totally cool. 

#4 Tell it like you see it 

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If your crush is someone you’re already friends with, then it would be more about being genuine than creative. Post a picture of your crush on Instagram and in the caption, write down 10, 20, even 30 things that you like about him/her and then 10 reasons why they should go out with you. Tag them! Nobody can resist going “aww” at that. 

#5 Insta-worthy feed Credit: IGNANT

Piecing together a full photo through uploading parts of it one by one to build up a 3×3 grid is kind of a thing now. Yes that’s exactly what we’re suggesting. Segment a photo of yourself holding a card with a message for your crush into nine parts and upload them accordingly. You could either tag your crush in the caption, or drop them a text telling him/her to check it out. With that being said, it’s one of the bolder moves on this list and we’d advise for you to only do so if you’re good friends (or at least on speaking terms) with your crush. 

#6 Subtweet/Subgramming 

Credit: Meme Generator

Subtweeting doesn’t always have to have a negative connotation to it. Sometimes your crush may tweet or upload an Instagram photo that’s reply-able. For twitter, you can post a witty subtweet that’s subtle yet relevant enough for him to notice it’s for him. For example:

Him: So bored, if only I had some company to grab coffee with.
(After a few seconds) You: Really could use a caffeine fix right now.

And if your crush has a knack for such hints, you’ll be getting that coffee date!

#7 Create a #hashtag story

Sounds tacky but it will always be cute. Come up with a sweet and witty personalised hashtag specially relevant to your crush. Following that, post a thread of Instagram posts, with each photo narrating from the first time he/she caught your eyes to hoping for a date with them now. Put that cherry on top by hashtagging each post with your unique hashtag! But go easy on the captions, it only takes a few overly-passionate words to escalate from an innocent crush to sounding like you have a creepy obsession… 

#8 The ‘push’

Making the first move for conversation and making the first move to ask someone out are very different. Sometimes the latter has a higher chance of success if the former is not done by you – removing the element of “creep”. However, many times your crush needs a little push. You can research through their various social media accounts to find out what they’re passionate about or feel strongly for. By expressing your opinion vehemently on those same topics online, when they chance upon it, they may feel the urge to start a conversation with you about it. From there, your chances of getting a meet-up is lookin’ pretty good. 

#9 From public to private

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Private messaging is never the smart first move. Start by sending a friend/follow request and see if he/she reciprocates. After the first barrier is passed, you can move on to liking or commenting on their photos. Give a good first impression of being just a friendly online follower. After several exchanges of replies and the niceness is still mutual, you’re ready for the PM to slide in the question. Remember, don’t jump the gun by being overly zealous and scare your crush away!

Do what you will with this list, but bear in mind to also respect your crush and their privacy. Sweeping your crush off their feet on social media seems great in theory, but everyone responds differently – just like asking someone out in real life, they too have the right to say no. And if they do, don’t keep broaching the topic online. Simply brush yourself off and move on with dignity and grace. 

Have any suggestions of your own to add onto our list? Comment below and share your tips! 

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