Even though I write about sex and relationships for a living, I am absolute shit at just about anything having to do with dating. I am the living embodiment of that old phrase “those who can’t do, teach.” Online dating gives me anxiety. I question pretty much every text message I ever send a member of the opposite sex. And, if I really like a person, I 100 percent lose the ability to flirt.
This last fact has always kind of perplexed me, because I’d consider myself a fairly decent flirt with people for whom I have no romantic interest. Having been a pretty successful bartender in my early 20s, flirting was something I had to learn in order to woo a few extra dollars from my customers for the martini I just shook them. I charm the absolute pants off of family members of significant others, and pretty much know exactly what to say to win a stranger over. But plop a man with tattoos and a strong jawline in front of me, and I go from “cute and flirty” to “bitchy and/or completely mute.”
Recently, I had a conversation with a friend in which she mentioned the magic of Instagram DM for flirting. She went on to talk about the dude in Berlin who she planned to meet up with during an upcoming trip to Europe, but my mind was elsewhere: I realized that I, too, used Instagram this way. And I was pretty good at it.
When I got home, I took a scroll through my Instagram messages and realized that, at first glance, things looked pretty innocuous. But dig a little bit deeper, and there were definite patterns in the way I approached conversations with a certain handful of people. There’s the guy who a friend tried to set me up with, but that didn’t actually work out, who I am constantly DMing about cats and restaurants in Brooklyn, coyly suggesting we go to together. There’s the friend-of-a-friend who, when I see him in person, I totally clam up over. But via Instagram, I flirt with reckless abandon. And then there’s the ex boyfriend who I haven’t seen in ages, but whose Instagram stories I respond to with abandon. They’re all men I’d date in real life, but our conversations only go down via DM. And I’m not alone on this — multiple friends who I’ve quizzed on the topic are also professional flirts via Instagram DM.
I couldn’t flirt with these men in real life. But pop the buffer of an iPhone screen in front of me, and I become Marilyn Monroe. It’s like I’m catfishing myself. The nervous, anxious girl suddenly turns into a world-class flirt over Instagram.
In truth, though, it likely comes from a heavy combination of fear of rejection. I don’t like flirting with men in real life, because I’m afraid that I’m going to make a total ass of myself. That, or they’re not going to like me — and I’m going to have to deal with that rejection face-to-face. That’s way too much for me to handle. But, much like an internet comment troll, hiding behind a screen means I can unleash. I don’t have to be afraid of sending a heart-eyes emoji, because if I don’t get the response I want, I can just delete it and forget it existed. It’s easier to play off a misguided flirt on Instagram. And since I can think out my responses, I become infinitely more witty.
But while flirting over Instagram can be fun, it also makes me question whether or not I’ll actually ever be able to connect with someone in real life — and that’s probably a fear I’m also not alone in. Dating is about being vulnerable, even though you know you may be rejected. If I’m afraid to take that step, and in my mind, that really cuts into my opportunities to meet someone.
That said, I’m trying to reframe my Instagram flirting, instead considering it more like practice for the main event. Maybe one day I’ll ask one of my faux boyfriends on the ‘gram out on a true date, and we can see whether my flirting has improved IRL. But until then, I’ll keep sending those emojis, waiting for the dude on the other end to make a move.