The Most Awkward Things About Internet Dating

There’s a lot of great things about internet dating. Like instead of awkwardly approaching a woman in a bar, doing it via email while sitting on the couch watching Family Feud. Or having your main competition be guys who take shirtless pictures of themselves in the bathroom mirror. Or knowing that no matter what happens, your first in-person meeting is going to lead to either a great connection or a hilarious story to tell your friends — or, at the very least, a colorful visit to the ER. But internet dating isn’t all romance and triage nurses. Believe me, I know. I’ve done my share of Internet dating, and a few other people’s shares as well, so I know there are plenty of ups and downs. Mostly downs, really. Alright fine, all downs, with an occasional up thrown in there that I’m pretty sure was an accident.

Seriously though, internet dating is great, as long as you can figure out how to minimize the awkwardness. Tell the truth in your profile, arrive at the date with a fun topic of discussion, don’t order shots with someone who could be a serial killer — all helpful tips to guide yourself out of uncomfortable internet waters. But there are some situations that are so awkward that there’s nothing really you can do. You just have to grin, bear it, and say to yourself “I’m never meeting someone while watching Family Feud again.” These are those situations…

When You Look Over on Your Internet Date and Realize You’re Sitting Next to… Another Internet Date: “Hey, look at those two! Fumbling for conversation, slowly nursing their white wines, laughing too hard at things that obviously aren’t funny. I bet they’re on a… oh wait.” Nothing makes you feel like a cliche faster than seeing your exact replica sitting across the bar, doing the same nonsense you’re doing. You didn’t feel weird before, but now you’re inexplicably self-conscious. Kinda like catching a glimpse of yourself in the mirror while having elaborate sex. “Oh God, is that what this position looks like? Could somebody hit the lights please?!”

When You Run Into a Date a Month Later: A few weeks ago, I was out with friends, and a girl came up to say hey to one of my buddies. We were introduced, and she looked at me like I had garbage coming out of my ears. “Hi…?” was my smooth and confident rejoinder. “Didn’t we go out on a date a while ago?” she said as aggressively as possible. And that’s when I realized two things: 1) She had drastically changed her hairstyle, and 2) I should’ve paid a lot closer attention when she said her name. Because the only thing worse than not recognizing an old date is not remembering her name from either said date or when just told it to you, two seconds ago. I know, I know. I’m a dick.

When OKCupid Recommends You Date A Friend of Yours: It’s weird enough clicking on a profile and discovering it’s your friend. “Oh, I guess Michelle’s an internet dater… and didn’t want anyone to know. That’s awkward.” But then, when OKCupid puts Michelle in your “Quiver” section, telling you that it feels you’d make a great couple, things get real weird real fast. Suddenly you can’t stop imagining you and Michelle on a date, holding hands, kissing french-style. “This was my platonic sisterly friend, and now you’ve ruined it!” you yell at your computer. Then click back over to Michelle’s profile to consider things further.

When You Email Someone A Second Time Without Realizing It: “You wrote me two months ago. In fact, you said some of the exact same things you just said now. Wasn’t interested then, not interested now.” That’s not a message you ever want to receive. Trust me. Why dating websites don’t have a “Hey moron, you emailed that person in July!” warning function is beyond me.

Receiving The “Thanks, But…” Consolation Email: On Match.com, they give you the option to send someone a gentle letdown email when you’re not interested in their advances. When you get a message you’re not keen on, you can reply with a form letter that says “Thanks for your interest, but…” and then select the reason why you’re bowing out. As if anyone cares at that point. It sounds great in theory, but what always happens to me is, I see a message in my Match in-box with a person’s picture and think “Oh hey, that cool girl wrote me back!”, then open the note to see the dreaded “Thanks, but…” intro. No one has ever professed their undying love to someone after using the words “Thanks” and “But.” Such a bummer. Honestly, I think it would be less deflating if they just wrote back, “You stink! Go Away!” At least that really jumps out in a subject line. Why can’t I find someone who will tell me I stink and should go away?!