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

Follow, like, and DM your way to romantic bliss.

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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 doesn't follow back, that's pretty helpful information. And if she does follow me back, I'll 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 other's photos every couple of minutes. Eventually we DM'd and went on a date."

For the record: he's 38 years old.

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 can't argue with results. So I called up a few dating and social media experts to compile the ultimate dos and don'ts of flirting on Instagram to help you follow, like, and DM your way to relationship bliss.

Do: Follow them before you slide into their DMs.

If you want to get someone's 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 won't 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 don't accept your request, don't request again. Sorry. They're just not that into you.

Don't: Like every single photo they post.

All of our experts agree that a mass liking of someone else's posts is a terrible idea that comes off as obsessive. If you are going to like more than one photo, though, here's 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 "it's not creepy if it's done tastefully," says Hecht. After all, you're an adult, and you know what you want. "Be light, funny, and engaging when sending the message," she advises. If you're reaching out to someone you've 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.

Don't: Send multiple DMs.

"The basic rule of social media flirting is don't be creepy," says Bennett. Repeat messages when you're not getting a response? Yeah. Creepy. Instagram messages have a handy feature that displays the word "seen" once the recipient has read the message. If your love interest has read your message but has not responded, take the hint.

young black woman in plaid shirt drinking coffee and smiling at her cell phone
Shutterstock/astarot

Do: Frame comments as questions.

The best way to get a response from someone you're interested in on Instagram is to simply ask them a question, according to Mae Karwowski, social media marketing expert and founder and CEO of Obvious.ly. "Comment on the content of someone's photo in a nice, non-aggressive way," she advises. "Make the comment a question about what is happening in the photo, not that person's looks. Remember, you are trying to start a dialogue," she adds.

For example, if you're leaving a comment on a photo of the person on a beach, say something like: "Your vacation looks amazing, how was it?" Do not write: "You look like a total smoke show." Simple, right? Right.

Don't: Say anything you wouldn't say in person.

Don't get weird behind the filter of social media. "A good guideline is asking yourself: 'Would I say this or do this if I saw this [woman] in person?'" says Bennett. "If the answer is no, then don't do it on Instagram either."

Do: Take things offline.

The end goal here is to meet this person in person, so don't prolong the online conversation when it's possible to go on a date and find out if you're right for each other. "Get out of a public newsfeed as quickly as you can," says Karwowski. "Say, 'I just DM'ed you,' and continue the conversation there. If that goes well, move to text, email, whatever you two want to do." Once you've both shown interest, there's no reason to waste time playing games.

Don't: Send mixed signals.

If you're not interested in meeting someone offline, don't pursue them online. "We need to stop hiding behind our devices," says Hecht. Ghosting, bread-crumbing, and cushioning have become easier than ever to do because of social media, and it's not a good look, especially for an adult man. "Be human," Hecht adds. Don't just reach out to someone to boost your ego or as a way to fill your time when you're bored.

overhead shot of a man and woman holding hands on a wooden table top
Shutterstock/Halfpoint

Do: Make your move and then let it go.

Overall, Karwowski has one all-encompassing rule for Instagram flirting: "Drop a hint once and then drop it, especially if you do not know the person," she advises. "Repetitive comments, likes, and other actions expressing interests do not count as actual flirting." If they don't take the hint, move on or seek out a more straightforward way to let them know you're interested, like calling to ask them on a date.

Don't: Rely on social media to get dates.

"The truth is that Instagram was not intended as a dating site, so it can be very confusing when it's used as one," explains Nikki Goldstein, sexologist and author of Single But Dating. "How do you know if someone is liking your photos because they actually like your photos or because they like you? There might be a few more obvious clues if they are sending you direct messages and asking you out for a date but e-flirting in terms of follows and likes can be misleading and confusing and leave someone asking, 'What does it mean?'" In other words, if you're really sure you like someone and you have the means to contact them outside of Instagram, that's probably a better bet.

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