How to Flirt on the Internet Like a Cool Handsome Guy

Dance like nobody is watching, DM like your boss is definitely watching.
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Illustration by Cécile Dormeau

Yes, the Internet is the home of Two Girls, One Cup, the alt right, and WebMD, but positive things also happen online. Mostly videos of soldiers returning to their dogs after war and Emily Ratajkowski's Instagram, but there is also: other people. And sometimes, you like those other people. Or even like-like!

You might be tempted to hit on these people whom you don’t really know by sliding into their DMs (or Snaps or Insta messages). But how? How can you convince the fitness model who just moved to Los Angeles who doesn’t have any idea who you are that you should be the one to show her the city?

YOU CAN’T. Stop that. If someone wouldn’t be into you in real life, approaching from the safe distance of social media is not going to help you. It’s only going to make it weirder. But that doesn’t mean no one ever is meeting online. Just be normal and not creepy. Here’s how:

Don’t be anonymous.

Nothing is creepier than someone with no photos of themselves online. It’s 2017. Having normal photos of yourself on social media is not going to ruin your career unless you’re in the CIA. Unless you’re saying really racist, homophobic, transphobic, sexist, ableist, etc. things on your social media, having photos up is NOT damning. The only people you get to approach if you’re anonymous are other people with Garfield profile pictures or whatever you’re hiding behind.

Don’t approach someone out of the blue.

An addendum to previous: the person you’re approaching should know you exist (i.e., follow you, at the very least) before you start hitting on them. I know movies will tell you otherwise, but being approached by random men is rarely romantic. Men who approach random women in movies usually look like Michael B. Jordan, and humans are programmed to find hot people not-creepy. It’s almost as jarring to show up in someone’s DMs to hit on them as it is to show up at their front door. Don’t do it unless they know who you are.

Don’t end sentences with "lol."

If you have to end a sentence with “lol” to negate the awkwardness of it, it’s a creepy sentence. Likewise, if you have to add a “haha,” you probably said a weird thing. Wink emoji, even if deployed ironically, are best left off the table too.

Don’t mention their appearance.

At literally no point do you need to tell an Internet stranger that you think they’re hot, sexy, etc. Wait until you’re on a date and the person has shown some miniscule interest in you in a romantic way. For example, when they walk into the restaurant on your first date, a simple “you look nice” will suffice. Otherwise, you just come across as lascivious. No one has ever turned a guy down simply because his message didn’t include mention of her appearance. That hasn’t happened.

Would you say that in front of your boss?

This is important! It’s not okay to tell someone that you’ve masturbated to them, that you guys would have cute kids, or that you really liked their last pic with all that cleavage. That’s gross. You’re hitting on us, we already know what you want. It’s as weird to approach someone online and tell them what you want to do to their body as it is in person. Dance like nobody is watching, DM like your boss is definitely watching.

Don’t fake date.

What’s a fake date? A fake date happens most often between people in the same industry. Here’s how it goes:

You: Would you want to meet up for coffee sometime this week?

Them: Oh, thank you, but I’m not interested in dating right now/ I’m very busy/ I have a boyfriend/ I have a girlfriend/ all my 7 parakeets died within 14 hours of each other so this is not a good time.

You: Oh, that wasn’t a date. I just wanted to see if you were interested in grabbing coffee to talk about your work. Um, but I guess not lol.

NO. No, no, no. We all know you were asking us on a date, otherwise you would have been more clear. Don’t try to sneakily undo your rejection and make the other person feel bad. No.

So that’s it: be normal. And not creepy. Oh! And definitely don’t send a photo of your dick. It’s called junk for a reason.


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