The 7 Worst Dating Disasters

Twenty-Something Tuesday

We’ve all had them, and suffered through them. There may be no social torture worse than the bad date, and yet we all risk it time and time again in the quest for the rare good date. Here are our tragic and terrifying dating tales of worsts and worsers.


The Dress

When I was 16, I met a guy at a party who went to our rival high school. He was one year older, and was therefore an exotic, desirable creature (plus, he was pretty cute). We went on a couple of dates, and he asked me to be his date to his semi-formal football banquet. I was super excited, as I would never get asked to a football banquet at my school, and wore a beautiful velvet burnout dress. Upon arrival at the banquet, I felt out of place because everyone else was dressed much more casually. Then I gradually realized this dude had no friends. Like, no one else talked to him all night. After that painful experience ended, we went back to his house to watch a movie. We were spooning on the couch when I felt him jerk up and then a wet sensation on my neck. He had fallen asleep and drooled all over me and my semi-formal dress. To the extent that I had to go to the bathroom to wash it all off. Aaaaand that was the end of that.

– Erin

Atheist Doctor

He picked me up from church before this date started, so that should have already given him a memo for what’s to come later in this story. I have a fear of dinner dates so I asked if we could just compromise with an ice cream date instead. He concurred! Off to a great start, right? Just wait. So we arrive at a Ma-and-Pa type of ice cream shop and we proceed to have what seemed like typical date conversation, such as… what’s our major and why. He says something along the lines of, “I’m pre-med because I think religion and believing in a higher power means you’re lazy. If you were better at science you would get it,” OK so don’t get me wrong, I am open to different perspectives. But the way I see it, if you have to force your own opinions down someone else’s throat—chances are you are struggling to believe in them yourself. At least that’s how I felt about Mr. Atheist Doctor. While he didn’t have a filter… neither did I. Match made in heaven. Without thinking, I asked him what time it was. I could have looked at my phone but before I knew it, the words blurted out of my mouth. He tells me the time and asks if I want to leave. I say yes because I’m tired.

It was only 8:30, but I wasn’t lying when I said I was tired… tired of his narrow-minded bullshit.

– Ella


Right after I met my now-boyfriend I went on a couple of dates with this guy who was really nice, if a little persistent. He invited me to go to a show with him, but I said things were getting serious with now-boyfriend. He said I should come anyway, so I ended up going (and having fun!) but he left something in my car. We joked that he had “Constanza’ed” me to see me again. When I showed up to return the item, I walked into an accidental date: He had wine and cheese out and a movie playing. I stayed for a glass of wine, but then made my exit. As I was leaving, he put a USB key into my purse. I tried to give it back to him but he wouldn’t take it. He walked me out to my car and still wouldn’t take the thing back. I drove to the end of the block, waited a few minutes, then drove it back to put it in his mailbox or something but he was STANDING THERE WAITING FOR ME. I got out of the car and tossed it underhand, saying, “Here, catch!”

As it was dark and drizzling, he didn’t see it and it hit him in the forehead. I shouted, “Sorry!!!” as I peeled away, while he searched through the wet grass for the electronic device. Later he texted me a picture of the mark on his forehead—I don’t envy him for having to explain how he got it.

– Erin

Too Little Too Late

The guy picked me up TWO HOURS after-the-fact of when we agreed on the date starting. Enough said.

– Ella

ID Please

One day I came home from work with an embarrassing amount of groceries and was bothering everyone else in my train car with how much space I was taking up. Then this cute, tousle-haired guy sat down next to me. Tousable hair kills me, for real. We started talking about how annoying all my groceries were, and then about music (second swoon), and then he offered to help carry them home. Outside my apartment, we exchanged numbers and agreed to hang out the next night.

So we start texting to set up this date. I suggest my favorite bar, and he replies “Um… I’m not actually old enough to go to bars.” Gulp. I’m 22 at this point, thinking “If he’s 20, that’s okay, I can work with that,” so we agree to meet at this coffee shop (that serves alcohol, because what if this date is terrible?)

We get there the next day, and I small talk for a second before blurting out “So how old are you??”

“19… in a few months.”

“I’m 22,” I reply, point blank, hoping this will end the date.

“Oh, that’s totally cool,” he says, “you still look really young!”

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And for some reason, this kid is not picking up any hints that EWW so I had to sit there while he drank his latte (and asked me to sneak him sips of the wine I was drinking) and told me stories about stealing booze from his friends’ parents’ liquor cabinets.

I have since learned to ask a boy his age before exchanging numbers. I also learned being a cougar is not that appealing. At least not yet. Maybe when I’m older, being told I still look young will be more of a panty-dropping line. Not yet.

– Kati

Alcohol and Douchecanoes

I had been chatting with a perfectly nice, nerdy, Doctor Who-loving guy on Tinder and planned to meet up for dinner. He mentioned briefly that his hair was longer than in his pictures, and that made me slightly suspicious. When he walks up, on a scale of 1 to 10 of attractiveness, he was maybe a 4—harsh but true. His hair looked like a wannabe mullet which I found horrific, and then he talked about politics and cars for half the night. So naturally I drank maybe one more glass of wine than was prudent, which means my barely-there verbal filter went to sleep. Abruptly I turn to the guy and sloppily said, “Your hair makes you look like a douche… Talking about Ferraris all night also makes you sound like a douche,” and then I had the audacity to giggle. Poor guy escorted me to my car, and thankfully left me alone after that. Consider alcohol my veritaserum

– Kelsey

Falling in the Worst Way

I’m really oblivious when someone has a crush on me. For any future suitors, you pretty much need a neon sign that flashes with the words, “I like you and want to take you out on a date” for me to get the message that you might just be interested. With this said, I went on an accidental date. I didn’t realize we were going on a date until the end of the night. We grabbed food, went on a walk, and he drove me home with the night ending at an unexpected kiss at my front door. So after that surprising twist to the night, I reached out to him and was very honest with him when I said that I wasn’t ready for anything and wasn’t interested in pursuing anything for than a friendship. He said he understood. Yet two weeks later, he surprises me at my university. I was an RA working freshmen move-in, so my phone was the last thing I was concerned with. I saw he was blowing up my phone but I didn’t have time to respond until I finally got off my shift which wasn’t until later in the night. I call him and he tells me to go outside.

… He didn’t go to the same school as me. Therefore, you could imagine how confused I was. But regardless, I went outside and there he was. He grabs my hands and he tells me he has fallen for me. Me having no filter I respond with an awkward vicious cycle of, “I’m sorry”, “I can’t”, “How?”, “Thank you”… with a grand finale of, “Drive safe?”

– Ella

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