The 11 Most Awkward Dating “Firsts”

The first time you do anything, it’s usually awkward. Regardless of what it is, too.

Updated 10 months ago, January 16, 2024

The first time you do anything, it’s usually awkward. Regardless of what it is, too. It could be the first day of school, your first college cafeteria – even your first time calling Uber because it just feels so pretentious until you realize it’s just so awesome.

However, the “firsts” when it comes to dating are the actual worst firsts and the list is pretty much endless. Dating is agonizing all its own, and the anxiety only intensifies any and every time a “first” comes up.

1. The first date. The texting leading up to the first date is sometimes cause enough to want to hide in your closet shamefully. You revert to your teenage self, first turning the volume up all the way so you daren’t miss a text, then switching your phone to completely silent (like, not even vibrate) and hiding it under six pillows because you just can’t take the waiting. Then, the date happens and is sprinkled with just enough awkward silences and ambiguous commentary to keep you up the next two nights, analyzing and sweating.

2. The first kiss. This may not happen on the first date (although, I always prefer it does because, otherwise, remind me again why we just spent the last few hours talking and laughing? So you could give me a goodnight side hug and send me on my way?), but it will happen at some point during your courtship. And it. Is. Terrifying. What if they suck? What if they think you suck (yeah right)? Will they use tongue? What if they don’t but you do? Will they go for your bottom lip when you clearly are the bottom lip kisser? The unbelievable amount of buildup that goes into a first kiss is the reason why I am a huge advocate of the surprise first kiss (attacking or being attacked at random) or the Annie Hall-esque, “let’s get this out of the way” first kiss.

3. The first sleepover. I vividly remember the first time I slept over at my new boyfriend’s apartment in college. It was a big deal. My friends and I consulted for hours beforehand about effortless sleepwear and made up an entire song about dry humping. When you’re trying to really date someone, i.e. not just bone them, the first sleepover is a big deal. Sometimes you’re invited, other times it’s understood. You came over for dinner, you guys have been cuddling on the couch watching movies, it’s getting late. You’re clearly not being sent home and you’re not about to suggest it either. The pair of you get to whoever’s bed by way of heavy petting and heated making out, and then you’re there, and you’re both drifting to sleep, and he rolls over to turn the light out, and you want to jump up and scream YAAAAAAAASSSS! But you don’t. Instead, you pretend to be a perfect sleeper by barely moving or breathing. You only get about 20 minutes of sleep all-in, but it doesn’t matter because, at this point in the game, even his accidental sleep farts are adorable.

4. The first sex. If you’ve handled the wait and build-up correctly, first sex lasts approximately two minutes. It’s not his fault – you guys have been treating each other’s genitalia like strip club patrons (you can look, but don’t touch unless you give me a lot of money, and even then…). A good way to gage sex is if you both giggle the first few times. If he doesn’t break concentration to acknowledge that stomach suction cup fart noise, he may be a sociopath. The great thing about sex, besides that it’s sex, is that it only gets better. So, if the first time is awkwardish and uncoordinated and not as vocal as you’d like, it’s only going to go up from there. That is, unless, sex is all they were in for. Then they’re a bastard and you’re going to cry – a lot.

5. The first pee. The lengths to which a girl will go to muffle her pee is astonishing. We pee all day every day, usually. We even force our friends to come with us to the bathroom and pee while they stare deep into our eyes. At home, when we’re alone, we pee hard and loud and maybe even make audible relief noises. But stick us with a full bladder in a new love prospect’s home, and watch us panic. I’ve had friends sneak off to the apartment complex bathroom to do their business. I myself have layered half the toilet paper roll into the toilet to conceal the sounds of my stream. At the beginning, something that you normally do mindlessly becomes one of the most anxiety-provoking actions. You go out of your way to avoid drinking any sort of beverage, and risk looking weird by excusing yourself to the bathroom at the bar or restaurant to ensure you are all clear before heading to one of your homes.

6. The first pee that takes an unexpected turn. Oh. My. God. This is what I assume to be most newly coupled persons biggest nightmare: the pee that goes schizo and decides to turn into a shit. It’s like as soon as you’re okay with using the restroom around your new person, your body laughs at your ignorance. “You’ll never be safe, bitch!” A pee turned shit should be accounted for under official “Top 10 Life Stressors” lists. I think the few times this has happened to me, I’ve silently cried on the toilet while texting my friends things like, “Welp. That’s that. I’m about to clog his toilet and run out. Fire up the Tinder!”

7. The first miscommunication. Just kidding. Every single miscommunication you have with a significant other is just as awkward and terrible as the first. They never get better. Unlike wine and other fine liquors, they do not get better with age.

8. The first fart. Someone’s gonna cut the cheese loudly and on accident at some point, and it could very well be you. You guys are screwing around, having an adult tickle war that’s bound to turn sexual in a matter of seconds, and PFFFFT! It just pops right out of you, as if to shout “This is so fun, right?!” It’s terrible and embarrassing and, if it smells, you should definitely grab your things and leave the premises immediately to decompress (and probably fart some more).

9. The first discovery of a rogue body hair. I can’t tell you how many of my girlfriends have been victims to their new boyfriends finding a pitch black body hair where it shouldn’t be. Many times, these boyfriends mistake it for a piece of lint or what have you and, without verbal warning, try to remove it from their girlfriend’s neck/chest/cheek/chin like a loving gentleman. Hormones change, and the charlatans that are these random body hairs come out to ruin your life and overall sex appeal. If this happens to you, remain calm, play dumb, and when he’s not looking, yank that sucker out with the force you use to yank corks out of wine bottles.

10. The first fight. Lord. The first fight after things have been going so well that you couldn’t possibly imagine what you could ever be mad at them for (so, say, around six months or so) is the pits. You’ve never felt more unsure and scared. You’ve also never dealt with this side of them before, so you’re terrified to play it all wrong. The first fight leaves both parties feeling defeated, like it’ll never be resolved and you’re forever broken. But, the good news is, if one of you isn’t a total psycho loser jackass stubborn prick face, you’ll get out of it just fine and probably stronger. Which leads me to the last first…

11. The first makeup sex. It’s worth the fight.