How to Flirt on Instagram: A Grown Man’s Guide

A half-generation ago, if you were romantically interested in someone, you did one of two things to fan the flame of their own ardor: You either flirted with them in person or flirted with them over the phone. How times have changed. A single friend of mine recently told me that his go-to, low-risk method of wooing is simply using social media. Yes, he has figured out how to properly flirt on Instagram. There are several non-creepy and even romantic ways to do it.

“Sometimes just following a [woman] can feel like a bold move,” he says. “But believe it or not, it works. If she doesnt follow back, thats pretty helpful information. And if she does follow me back, Ill just start liking a photo or two and see where things go… Recently, I got into a back-and-forth with a [woman] in which we kept wordlessly liking each others photos every couple of minutes. Eventually we DMd and went on a date.”

Now, whatever you think about this safe, distanced, and even childish way of flirting (for the record: I would urge all men to pick up the phone, always), you simply cant argue with results. So I called up a few dating and social media experts to compile the ultimate dos and donts of flirting on Instagram to help you follow, like, and DM your way to relationship bliss.

How to Impress a Girl on Instagram: 10+ Playful Tips That Work
  1. 1 Come up with a strong bio.
  2. 2 Make your profile pic a good one.
  3. 3 Post fun and interesting content.
  4. 4 Use high-quality images and fun filters.
  5. 5 Add killer captions.
  6. 6 Include some video posts.
  7. 7 Don’t forget your stories!
  8. 8 Follow her if you don’t already.


Do: Follow them before you slide into their DMs.

If you want to get someones attention, follow them. “Most people view who their followers are and if the other person follows you back, you are already ahead of the game,” says Jen Hecht, president of The Dating Advisory Board. This is one action on Instagram that really wont be perceived as too aggressive by anyone, regardless of whether you know them in real life or not. But one word of caution: If you request to follow someone who has a private profile and they dont accept your request, dont request again. Sorry. Theyre just not that into you.

Don’t: Like every single photo they post.

All of our experts agree that a mass liking of someone elses posts is a terrible idea that comes off as obsessive. If you are going to like more than one photo, though, heres one salient piece of advice: “I advise guys to like a variety of pictures, not just selfies and sexy photos,” says Jonathan Bennett, certified counselor, dating expert, and founder of The Popular Man. “Build a rapport and get to know her by actually exploring photos that reveal more than just her looks. Women know what a guy is after when he only focuses on the sexy photos.”

Do: Send a thoughtful DM.

Ah, to direct message or not to direct message? Sometimes, it might seem like sending someone a DM is a little bit too forward, but “its not creepy if its done tastefully,” says Hecht. After all, youre an adult, and you know what you want. “Be light, funny, and engaging when sending the message,” she advises. If youre reaching out to someone youve never met before, be especially careful to keep things appropriate. “How would you reach out to a prospective business client if you were trying to set up an initial meeting? The same principles apply reaching out to a love interest,” Hecht posits. If you already know your love interest, however, skip the DM and text or email them instead.

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