Breakups are inherently messy and awkward. You’re ending things with someone you loved — there are bound to be hiccups. One of you is probably going to ugly cry.
But some breakups are next-level awkward. Below, funny people share the most cringe-inducing breakups they’ve ever experienced or seen firsthand. Read ’em and weep (and just be glad they didn’t happen to you).
1. The one with the booty calls
“One thing I have learned as a rideshare driver is that if a man is getting a car in the middle of the night, is carrying suitcases but is not going to the airport, he’s done something wrong. I picked up one such dude at 5 a.m. in Silverlake, Los Angeles, and he immediately started calling and texting girls that he had been chatting with on Tinder and asking them if they wanted to ‘hang out.’ Nobody was that interested in hanging out at five on a Wednesday morning, or in fact in talking to him at all, so eventually we had to find him a hotel to move into.” ― Virginia Jones, a comedian and actress in Los Angeles
2. The one with Kenny Loggins
“One of my friends from high school was going out with this girl but had an epiphany while driving. A certain song came on the radio, and he realized he wasn’t meant to be in a relationship. When the girl asked why he was breaking up with her, he said, ‘Sorry babe, can’t be with you. “Danger Zone” opened my eyes to where I’m at in life right now.’” — Josh Womack, a co-founder and the head writer of Laugh Staff
3. The one after the first date
“I had just hit that dating sweet spot: My last boyfriend was far enough in the past that I was having a great, guiltless, tear-free time going out with people, but not so far away that I wanted another relationship. I met this guy at a bar. We’ll call him Eric. He had a guitar, and that was it for me. I’m a total sucker for the creative type. We went on a date, had great lingering eye contact, everything was going well. I remember thinking, ‘Hell yeah, I’m gonna see this dude naked tonight.’ After dinner he walked me to my car, and we started fooling around. Right when I was about to tell him to get in his car and follow me to my place, he broke the kiss and said, ‘Hey, so I think you’re great, but I’m not looking for anything serious.’ To which I replied, ‘Yeah, man, you’re fingering me in the parking lot of a karaoke bar. I’m obviously not trying to be in a relationship.’ It got real awkward, we each retreated to our cars, and I didn’t see him again.” ― Ariel Elias, a comedian in New York City
4. The one with Taco Bell and soiled sheets
“Not too long ago, I was in a place in my life where my basic integrity could be compromised for a mean guy with a beautiful dick. My stupid ass ignored a bunch of obvious red flags like him screaming at me for not using coasters or telling me that Korean was his favorite type of Asian. One night, after a ‘come to Jesus’ moment at a Taco Bell near his house, I went over to break up with him but ended up having sex instead, due to the aforementioned dick. The whole time we were having sex, I was fantasizing about how to break up with him. But then out of nowhere, he screamed, ‘Call me daddy!!’ which shocked me so much that I pooped on his white Ralph Lauren sheets. His face contorting in blind rage, I slowly backed out of his room and out of his life, forever. I’m pretty sure that’s ghosting?” ― Peter S. Kim, a comedian in Los Angeles
5. The one with the sad sandwich
“One dude I knew used to leave for work at 6 a.m. and stop by the bodega. He’d buy himself food and leave a bacon, egg and cheese for his girl, paid off, that she could pick up when she left at 7:30 a.m. It was cute. One day, I walk into the deli, and she’s mad that the counter guy was charging her, and he had to explain that her boyfriend didn’t leave it paid off. She called him and found out that their argument/breakup last night was real. She had it on speaker phone, so we all learned about the breakup together. She cried. Then we all chipped in a paid for her sandwich.” ― Gastor Almonte, a comedian in Brooklyn
6. The one with the podcast
“I broke up with my boyfriend (and talked about all of my issues with him) on my podcast. One night after the breakup, I ran into one of his friends and had sex with him in the bathroom of a bar. It wasn’t the greatest. He even pleaded at the end, ‘I can do better,’ so I also told that story on my podcast. I started dating my boyfriend again, and he listened to my podcast. He showed up to one of my comedy shows with his friend and said, ‘We both break up with you,’ and threw a drink in my face, but we were broken up.” ― Mara Marek, host of “The Happy Never After” podcast
7. The one with the sax player
“When I was in high school, I was madly in love with the baritone sax player in a band, and since I played the oboe and we were both woodwinds, it was already a love forbidden. He was very into the sax. He wouldn’t hold my hand or hug me without moving his fingers like I was a human saxophone, which I think he thought was sexy but mostly made me feel like a saxophone. He was older than me and ended up majoring in saxophone in college (a thing that you can do) and broke up with me so he’d have ‘more time to practice.’ I was completely devastated and for years thought he had cheated on me or met someone else and didn’t want to hurt my feelings. Then I saw him a few years later, long after we were both over it, and he confirmed: He actually broke up with me for the saxophone. And it had worked out. He was really good at the saxophone now. Also, he had a Foghorn Leghorn tattoo by that time but didn’t care to explain it.” ― Jamie Loftus, a comedian and cartoonist in Los Angeles
8. The one on New Year’s Day
“My 2018 started out rough. I got dumped by a girl on New Year’s Day. Apparently, her resolution was to not date me this year.” ― Joshua Morrow, a comedian in Cleveland
9. The one with the ice cream
“My boyfriend came over and surprised me with Thrifty ice cream. We sat in my living room and talked for a bit before he suggested we move to my bedroom. He kept looking deeply into my eyes, and as I got up off the couch and into my wheelchair, he rubbed my ass and told me I looked pretty. We quickly moved to the bedroom and got under the covers. I moved in to kiss him, and that’s when he broke up with me. This was two days before Christmas.” ― Danielle Perez, a comedian and actress based in Los Angeles
10. The one with the dramatic fall
“This didn’t happen to me, but my friend Paula was having a fight with her boyfriend who was visiting from France and was being a stereotypical French asshole. It was New Year’s Eve, and we were all at a huge party, and he was wearing a big puffer jacket with a detachable hood. As they were arguing, I decided to help my friend and start yelling at him too. He was fed up with the two of us, but I wasn’t done with him, so as he walked away, I grabbed him by the hood, thinking I had him. I soon felt the hood detach in slow motion, snap by snap, and I fell down a small flight of stairs, hood in hand. As Paula ran to my aid, she yelled, ‘Jen! I see your vagina. Where are your panties?’ Oh, and they never spoke again.” ― Jenny Saldaña, a comedian and actress in New York City
