Your Most Bonkers Breakup Story

Illustration for article titled Your Most Bonkers Breakup Story

Breakups are responsible for some of the world's best pop songs and worst poetry. And most memorable stories.


I once got broken up with while dressed like a "sexy" Catholic school girl at a Halloween party at my then-boyfriend's apartment. I had to walk home by myself dressed like a circa 1999 Britney Spears. I was 22 years old, and it was the worst walk of my life. Now, the better part of a decade later, it's hilarious.

Jezebel EIC Emma Carmichael was broken up with by her fifth grade boyfriend thusly,

Fifth grade, recess, 'boyfriend''s best friend approached me and my girls, says: '__ wants to break up with you.'

I say 'Why?'

He says, 'Because when you take a ride on the train, you take a ride on the [screaming] HOOOOOOO, TRAIN!'

Runs off.

End scene.


But before we get to your tales of heartbreak made hilarious by the laughing gas of time, let's talk about the most ridiculous lengths the horny among us have gone to have sex. Wren would steal a car and climb a tree three times a week. BurntEditor flew international to reconnect with a one night stand. The always entertaining CanIHave4Beers broke several bones in an attempt to impress a dude she enjoyed banging. But this week's winner is SciFriedMyBrain. You'll see why.

Clowns. My best story involves a lot of clowns.

I mean, I have other stories. Honorable mention goes to the time I had sex on the 5th floor of a hotel's glass-walled staircase in plain view of the street below because we couldn't afford to get a room in said hotel, and the time I swam out to the center of Walden Pond during a summer afternoon to get my aquatic nookie without ruining view my fellow Thoreau enthusiasts. Having written this down, I acknowledge I might be an exhibitionist.

Exhibitionism aside, I never planned on having sex in a room that felt like the inside of a circus car. You can't plan for this kind of thing. You see, I hadn't had sex in a year when I struck up a conversation with a lovely ginger haired fellow at my local bar about what silly movies we liked. I was willy to bang anything human that seemed moderately competent. So I didn't really notice that the ginger fellow really only started hitting on me in earnest when I mentioned I like the movie Killer Klowns from Outer Space. He had nice eyes and the most gorgeous curly red hair. I wasn't worried when he showed me a picture of his recently deceased cat named Krusty. He had a great sense of humor. I didn't really study his bedroom as we tripped though it shedding our clothes. But when my makeout partner tipped me onto his bed, stripped my panties and began eating me out, my eyes flew open. The world swam into view. I was surrounded by clowns. Dolls. Posters. Action figures. Shelves of ginger haired leering clowns with dead porcelain eyeballs. And yet... I was getting eaten out. I've never felt more conflicted. Stay for the cunnilingus or flee from the clowns. I closed my eyes, trying to pretend that I didn't just see that. I laid there trying to focus on what my clit was feeling. Failing, I put my hands in my partner's hair... his red, curly, bozo like hair. I shudder. My partner takes this as a sign of good things and sits up, reaching for the table at the side of the bed. I open my eyes and what do I see... another clown. He has a tattoo on his chest... of another clown.

In that moment I seriously questioned if I was actually awake. I gave serious thought to the idea that I was dreaming this as punishment from my nookie-deprived libido. I was never afraid of clowns, but I never thought I would be turned on while looking at them either. It was at this moment my partner decides to apply a small finger vibrator to my clit. I come with all the relief and horror of a year of abstinence under the watchful eyes of a score of smiling clowns. I decide I am, in fact, actually experiencing this in real life.

For the rest of the night, we fucked with the lights on. I wanted it bad enough and the sex was oddly spectacular. Not even a flock of clowns could stop me.

This was 8 years ago. I have avoided circuses and performers at street fairs ever since. I'm not scared. I just still get turned on.

This sounds like the greatest episode of SATC that never aired.

With that, please make sure your seat belts are secretly fastened and your tray tables are in their full upright positions as we take off to Dumpsville, population: millions.

Image via screengrab



My freshman year of college, I made the mistake of dating a very serious born-again Christian. (I was raised both Catholic and Unitarian Universalist, I'm not sure what he was doing in the relationship either.)

The relationship went well enough for the first few months, despite several red flags - the plethora of Bibles, his pressure on me to convert, etc. A few months in, he was cast as the lead in the play at his church, "Spiritual Warfare." It was really important to him and he was very excited about it. So, being a supportive girlfriend, I bought a new dress and went to see it.

The basic plot was that Adam was a youth minister at a small born-again church (just like in real life!). But he was too successful at converting youth! And so the devil sent several demons to tempt him. The demons of alcohol and rock and roll were useless against his spiritual prowess, though, and Adam persevered. I am snickering in the audience as quietly as I can.

The kid playing Satan then had a great idea - "I'll send the Demon of Seduction!" The Demon of Seduction then appears as another college aged student who entices Adam into a relationship, taking him away from his youth ministry. Adam falls head over heels for the Demon of Seduction. I am now saying "OH SHIT" to myself in the audience as he calls the character by his little pet name for me.

Adam's character then has a long monologue with Jesus about how he can't date this girl because he can't marry her because she hasn't accepted Jesus as her personal lord and savior. So, sitting in the audience, I am pretty sure I have just been dumped. In front of an entire church of people.


The play then ended with singing, chanting, swaying, etc. A pastor gets on the microphone encouraging anyone who needs Jesus to come pray. Well, being raised Catholic and having a nephew born the day before with a collapsed lung, I approach the front, intending to kneel and say a little prayer for the baby.

Adam was glowing as he saw me approach, he must have though the play got through to me. But Adam didn't approach me, some other girl did. She grabbed my hand, got up in my face, and shouted, "You TELL it to JESUS! You LAY it at the foot of the CROSS!!"

And that's when I ran. And hid. In the Sunday School classrooms. Where Adam eventually found me and told me the play had really hit home and he could not keep seeing me, as I was clearly the demon of seduction sent to sway him from his ministry. I laughed so hard I cried.