Dating has certainly evolved over the years—we’ve gone from courtship being purely a financial arrangement (not that this trend has ever truly died) to knights jousting for a lady’s favor, to casual hookups … and now, romance is primarily found through an app more than anything else.
Technology used for meeting that special someone has become so advanced that you can base your search entirely upon specific interests. Like … oddly specific interests. Think a fellow cat person would be the purrfect match? There’s an app for that. Wish to “love long and prosper” with a fellow Trekkie? There’s an app for that too.
No matter the changes, one thing remains the same—dating is awkward. It’s got all the unspoken formalities of a job interview, disguised as innocent fun. The balance between playing it too cool and too eager is hard to find even for the smoothest among us, and usually results in total embarrassment. Even if we aren’t the ones committing those embarrassing acts ourselves, we are often the reluctant witness to them.
Terrible dates might not always be fun in the moment, but they can be just as important as the good ones. They can teach us a lot about ourselves and what qualities we want in a partner. And at the very least, they can teach us to embrace social clumsiness with a sense of humor.
Jimmy Fallon recently asked his “Tonight Show” audience on Twitter to share a “funny or embarrassing first date story” for his ever popular #Hashtags segment. The best part—some of these awful first dates ended in marriage. There’s hope for us all.
Below, find 15 stories that are truly the best of the worst. How do some of your first dates compare?
1. “After a nice dinner, she invited me to her house. On the way up, inside the elevator, I decided to push the button to stop between floors and give her a kiss… She had a phobia of closed spaces and she smacked my face as a reflex, two punches after we were kissing and laughing.” – @PanqueAlgarvio
2. “His jeans were so tight he couldn’t sit down. Stood at a bar stool the whole time.” – @onlyintheozarks
3. “Waiting 4 my date when an older couple asked me for a ride. my date came up and said sure! We drove them home & they asked us to come in. Date said “sure”. I pulled him back & asked why he wanted to hang w/strangers. He said ‘sh@t! YOU DON’T KNOW THEM!?’ We bolted!” – @natashaham75
4. “Before the date, we had been chatting about books we liked and I talked about a great book I just read. We went on the date. I loaned her the book. She ghosted me.” – @thenextbarstool
5. “The worst first date I ever had was when my date locked his keys in the car and I had a curfew so he had to break his car window out to get me home on time. Didn’t think I’d ever see him again but we wound up married.” – @csleblan
6. “First date movie ‘Basic Instinct’ not realizing how suggestive it was. We just thought it was a mystery thriller! We left the movie discussing how each character could have actually murdered someone. We’re married now.” – @Southrnbell_Amy
7. “First date with my ex husband was a double date with his parents. The preview for ‘Speed Racer’ came on, and she leaned over me to say to her son, ‘You know what your dad’s nickname in the bedroom is?’” – @theostoria
8. “A friend asked me on a double date as a blind date with his date’s friend. I went to the bathroom and came back just in time to hear my date say to her friend, ‘why do I get the ugly one?’ I said good night to all three and headed home, leaving her w/the bill.” – @StevenTrustum
9. “He loved cheese. I was subjected to a 2 hour conversation/lecture about cheese, and why cottage cheese is not cheese!” – @Optimist_Eeyore
10. “He took me to an Asian fish market. We walked around looking at live & dead fish for a while. I don’t like seeing dead animals & I don’t eat seafood. Then we sat on a curb & he pulled out a ziplock bag of pineapple for us to share. I don’t like pineapple.” – @markayhali
11. “My cousin set up a first date for me with a family friend. During a break from dinner, Mr. Man follows me into the ladies’ room, comes up close and says in a low voice, ‘I shave my butt.’ Can’t remember what I said in response but the evening ended abruptly.” – @carli_zarzana
12. “I once took out my high school crush to a sports bar and ordered the spiciest wings there in an attempt to impress her. Not only was she not impressed. The next morning I woke up with heartburn.” –@Dmonster38
13. “My date showed up with his bestie and girlfriend, and they talked through dinner about people I don’t know. Walking to the car, he gave me a wedgie because he thought he hadn’t been paying enough attention to me.” – @surrealDazey
14. “I was taking my date home and was pulled over by the police for speeding. When the cop came to my car, she jumped out and told him she had to get home. She walked home and I never heard from her again. I’m not sure who’s #WorstFirstDate it was mine or hers!” – @eastriverbear
15. “After an evening of dancing with a first date, leaving the dance hall, I had to take a quick pee break. Rushing out to the parking lot, I see a lady, I grab her and swoop her around, and plant a big wet kiss on the lips. She was another guy’s wife. Oops!” – @seadogskamore
This article originally appeared on 9.22.22
