• Thu, Jan 30 - 3:30 pm ET

Our 10 Best/Worst Awkward Dating Moments, Complete With Gory Details

photo: YouTube

photo: YouTube

That Awkward Moment, a bromance comedy starring ageless Clearasil ad Zac Efron, Miles Teller, a Michael Jordan that does not play basketball and some babe named Imogen Poots (OK, seriously, when you become an actress you can change your name to ANYTHING and you changed to “Poots”? REALLY? I want to be so hot that I call myself “Poots” like it ain’t no thang) hits theaters tomorrow.

The titular awkward moment is supposedly when you have a come-to-Jesus meeting over where your relationship is going. The trailer leads me to believe this movie is mainly awkward because of men and their man feelings. In my world, awkward dates usually involve less feelings and more bodily harm.

Here are our stories.

1. One summer, my boyfriend at the time and I were both in between apartments. His parents own a house in a remote mountain town that was between tenants, so we got the luxury of playing house for a month in this empty house in the most gorgeous area. I had very little to do all day but play housewife, lots of baking and reading and angstily writing by the lake. One night I decided to run a romantic bubble bath and got a little carried away with the tealights. We got in, all seductive-like, and everything was very sexy for the two minutes before my BF softly whispered that my hair was on fire. Those are words no hairsprayed woman wants to hear. I screamed, flailed like I was drowning, and submerged my whole head in the very crowded, very hot tub. My makeup and the vibe was ruined.

Moral: Tealights are the devil and I can’t be trusted with fire.

I was feeling mighty bad about myself remembering this until a girlfriend told me about the time she broke her nose on a date. Seriously, broke her nose.

2. “My bootlace got caught in the passenger door when I tried to be chivalrous and close the car door for my date. I face planted on the curb, and my nose started gushing immediately. I got back in the car, and she was like, “OMFG ARE YOU OK?” and I was like, “Ohhhh I’m fine really, just a nosebleed.”

“I drove back to her place seeing stars the whole time. And when I turned to say goodbye to her, she basically gasped in horror because my nose had swollen into a purple blob. She gave me a hug and my nose grazed her cheek and I just squealed in pain.”

I had to ask for a follow-up.

Mandie: Did you continue to see each other?

Dani: Yes. Small Virginia town = very limited gay dating pool. She had limited options, which is why I think my charm held out past that date.

Mandie: Also, you are chivalrous. Remember that.

Dani: Yes, I am a brave knight, facing the curbside dragon.

Moral: Chivalry is dead because it kills people.

Next, I asked my very cool roommate. What I found backed up my quickly forming theory that girls in love (like) suffer from a lack of spatial reasoning.

3. “OK, so this one goes all the way back to high school. I was having dinner at my boyfriend’s house for the first time ever, and meeting his whole family. After dinner, he walked me to the door and gave me a hug. I was so distracted by his parents that I turned around and walked straight into the glass door.”

“And it wasn’t like, a light tap. It was full on, head first, banged my skull full force against the door. And his parents were all standing right behind me.”

Moral: Zooey Deschanel/Jessica Day really does know our life.

Of course, not all of my stories involve injury. There was also the only time I ever dated a fellow redhead. Everything was awesome, except people constantly asked if we were brother and sister. Squicky.

Here’s one from our very own Sam.

4. “I got out of a shitty relationship toward the end of my senior year of college at the age of 22, so I briefly did a bit of OKCupid-ing. I was on a date with this guy who seemed like a fairly normal, albeit very cautious, person– he wanted to Skype briefly prior to meeting, which made sense but was still a little odd. He asked if we could meet up at a bubble tea place, which made sense since cautious people may not love having first dates in quiet, dark lit bars. I got there and he looked considerably younger than I had thought, but some people just have young faces (Hi, Toby McGuire, eternal 18-year-old), so I brushed it off.”

“Then, when he didn’t order a drink at the restaurant we went to, I just got curious and asked his age. Turns out, dude was an 18-year-old. Who had just graduated high school a year late. And I felt like a creep. Except he was also a creep, because when I decided to just finish my meal and leave soon after, he said, “So, are you into anal stuff or not really?” Aaaand scene. I was out.”
Moral: Only weirdos suggest sucking down oversized tapioca on a first date.

5. We also have that awkward moment when your friend gets a Facebook message five years post bang that she took someone’s virginity.

6. Or that awkward moment I taped my phone number to someone’s windshield (I was sixteen!) and was then surprised to be outed as a crazy person.

7. Or that awkward moment I caught my belly button ring on a chain link fence and had to cover up the blinding, searing pain so I wouldn’t look uncool to whatever skinny jean wearing person I was trying to impress by scaling fences.

8. Or that awkward moment in seventh grade I was dumped with an origami folded note by someone that couldn’t be “unequally yoked” to a non-believer.

9. Or all those awkward moments when my friend’s subletter left her glass dildo in the dishwasher.

10. Or that awkward moment last month when I flipped a hammock trying to be seductive. Into a foot of snow.

Tell me your horror stories! I would bet money that That Awkward Moment ain’t got nothing on us.

You can reach this post's author, Mandie Williams, on twitter.
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  • Lindsey Conklin

    bahahaha Sam! “so are you into anal and stuff?”

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  • anna

    “6. Or that awkward moment I taped my phone number to someone’s windshield (I was sixteen!) and was then surprised to be outed as a crazy person.”

    that’s SO MEAN. I would do that now, if I liked someone and didn’t get another chance to exchange numbers after meeting them in say a parking area. I would never intentionally humiliate someone who liked me enough to leave me their number.
    Person who did this, they weren’t worth it.