The True Story Of The Most Awkward Night Of My Life

The True Story Of The Most Awkward Night Of My Life ©iStock/themacx

I’m a millennial and yet I’ve only had one hook-up in my whole life. I know, that seems super crazy. But after experiencing a serious relationship, I’d rather be single until I meet the right person than see a bunch of people casually. When I was 22, I was introduced to a guy who was a few years older by a mutual acquaintance. We had a traditional dinner date and then for our second so-called date, he invited me over to his apartment to watch Wet Hot American Summer. Besides the fact that he’s the reason I’ve never seen that entire movie, it was a truly awful, awkward evening. I would go so far as to say the single most awkward night I’ve ever had. Here’s why casual hook-ups just aren’t for me.

  1. I felt bad about myself. Of course, there are tons of people that are just fine with something casual, and all the power to them. There’s nothing wrong with that. But there’s a fine line between knowing you can handle a hook-up and knowing it’s just not for you. I never really considered whether I was pro or anti-hook-up, I just knew I liked the guy and he was kind of funny. But the evening was awkward since we barely knew each other and I left feeling pretty terrible about myself, which is definitely not a good thing.
  2. Second dates are always awkward. Just like first dates can be anywhere from magical and fun to totally boring and dull, you can’t escape the inherent awkwardness of it. A second date is still slightly awkward because you’re figuring out if you still like this person, if you can see yourself with them long-term, if they want the same things, etc. So adding a casual hook-up to the mix on your second date? A recipe for disaster, at least for me. Second dates are super important, and it’s not a bad idea to save all the physical stuff until later. After all, if you’re in a relationship, that kind of goes with the territory, and it won’t be awkward at all.
  3. He wasn’t super nice. That one evening is all I have to judge the whole casual thing on, and since it wasn’t a pleasant experience at all and the guy was kind of a jerk, hook-ups just aren’t for me. Moving on.
  4. I want something meaningful. OkCupid, the great love philosopher of our time, asks a question, “Is love or sex more important to you?” They figure if you answer it you’ll find your matches much easier (but their system involves all kinds of Math and so that’s when I lose interest). Basically, I want love, and I won’t settle for anything less.
  5. I don’t want to be one of many. Chances are, if you’re in a casual situation with someone, they’re doing the same thing with a lot of other people. You don’t really have any right to ask because, hey, you guys haven’t committed to each other. It’s kind of sketchy. Exclusivity and hooking up don’t usually mix, and so it’s definitely not for me.
  6. My dealbreakers are pop culture related. I’m joking… kind of. Kissing is definitely an important aspect of any relationship, but before I decide whether or not I want to kiss you, I need to know if you are a fellow pop culture person. What shows keep you up at night, both because you can’t stop watching yet another episode and because you’re thinking about the plot and characters? What good/bad horror movies are you into? So, hook-ups are not a good gauge of pop culture compatibility. I basically need a first and second date to make sure we’re a good cultural match.
  7. I want to tell a good story. Even if it’s just that we chatted on Tinder, I still want a cute origin story for whoever I wind up with. I don’t want to meet my girlfriends for drinks and swap hook-up tales, that’s just not me. Even if my hook-up somehow magically turned into a relationship, that still wouldn’t be a good enough story. I’m a writer, so it’s all about the storytelling. Can’t help it.
  8. My friends have told me the worst stuff. We’re all different, we all want different things out of life and love and that’s okay. But some of my friends have told me stories about when they’re been involved in something casual, and – no surprise here – the stories are never pretty. It’s enough to make me want to run away from any mention of Netflix and chill (and that breaks my heart because I love Netflix).
  9. I would worry too much. Like many of us, I’m a bit of a worrier. I don’t need anything else to worry about, and if I was involved in something super casual, that’s all I would be doing. No thank you. I’m just fine here, watching Lifetime movies unironically and tweeting about my TV obsessions.
Aya Tsintziras is a freelance lifestyle writer and editor from Toronto, Canada. In addition to writing about dating and relationships for Bolde, she also writes about movies, TV, and video games for ScreenRant and GameRant. She has a Political Science degree from the University of Toronto and a Masters of Journalism from Ryerson University. You can find her on Twitter @ayatsintziras and on Instagram @aya.tsintziras.