The Grown Man’s Guide to Flirting on Instagram

How to follow, like, and DM your way to romantic bliss.

The Grown Man’s Guide to Flirting on Instagram

How to follow, like, and DM your way to romantic bliss.

If you liked a girl roughly a half-generation ago, you did one of two things to fan the flame of her interest: You either flirted with her in person, or you flirted with her by calling her on the telephone. How times have changed. As a single friend of mine recently told me, his go-to method of (extremely) low-risk flirting is simply using Instagram. “Sometimes just following a girl 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 girl 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 wildly hands-off, distanced, and even childish way of flirting (for the record: I would urge all men to pick up the phone, always), the reality is you simply can’t argue with results. So I called up a few dating and social media experts to compile the ultimate do’s and don’ts of flirting on Instagram to help you follow, like, and DM your way to romantic bliss. And for more high-tech ways to meet the woman of your dreams, here are The Best Dating Apps if You’re Over 40.

1
Do: Follow Them.

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 the app that really won’t be perceived as too aggressive by anyone, regardless of whether you know them in real life or not. 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. She’s just not that into you.

2
Don’t: Like Every Single Photo They Post.

All of our experts agreed 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.” For more great ways to impress the fairer sex, here are The 15 Ways to Impress Any Woman.

3
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 a grown man and you know what you want. “Be light, funny, and engaging when sending the message.” 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,” she says. If you already know your love interest, go ahead and text or email them instead.

4
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, so if your love interest has read your message and didn’t respond, take the hint.

5
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 smokeshow.” Simple, right? Right. And for more great dating advice, here are The 10 Ways That Prince Harry Won Meghan Markle.

6
Don’t: Say Anything You Wouldn’t Say In Person.

Don’t get weird or “out there” with any of your communication. “A good guideline is asking yourself: “Would I say this or do this if I saw this girl in person?’” says Bennett. “If the answer is no, then don’t do it on Instagram either.”

7
Do: Take Things Offline.

The end goal here is to meet her IRL, so don’t prolong the online conversation when it’s possible to just 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. “Either say ‘I just DM’ed you’ and continue the conversation there. If that goes well, move to text, email, whatever you two crazy kids want to do.” After all, by this point in your life, you know what you want, so there’s no reason to waste time playing games. And once you get that date, be prepared to impress her with The 10 Sexiest Things to Say to Her On a First Date.

8
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, breadcrumbing, and cushioning have become easier than ever to do because of social media, so it’s important to take extra care not to do these things to someone else. It’s not a good look, especially for an adult man. “Be human,” she adds. Don’t just reach out to someone as a “back up” or as a way to fill your time when you’re bored.

9
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 IRL. Repetitive comments, likes and other actions expressing interests do not count as actual flirting,” she says. 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.

10
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 Dr. 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. For more insight on how to make your dating life easier, here are The 12 Rules for Dating a Colleague.

For more amazing advice for living smarter, looking better, feeling younger, and playing harder, follow us on Facebook now!