19 Embarrassing Breakups That Have People Cringing

As universal as breakups are, no one is the same.

You might cry for weeks at some, feel relieved with others, and then cringe just thinking about the rest.

We're talking about the latter today. These are the breakups that no amount of Ben & Jerry's ice cream can solve. Instead, you might just need therapy.

If you can handle the cringe, here are 19 embarrassing breakups.

The fake death.


This one's a doozy.

This girl broke up with her boyfriend because he was always testing her loyalty. Well, she found out later that he had overdosed on pills... or so it seemed. He texted her the next day saying he tested her to see how she'd react.

The reminder.

Unsplash | insung yoon

"I dated a guy casually for about two weeks during my senior year of high school before I realized it wasn't going to work. So I met up with him and told him in person. Well, later that night, I got a long text about how disappointed he was. He ended it with, 'Don't forget to set your clock back this weekend.'" -blaynee2

The high five.

"I once broke up with a girl, after a nice half hour conversation of why things weren't working, then proceeded to give her a high five...awkward for both parties involved." - u/Icanhazreddit

The name.


This Redditor dated a woman for two months without knowing what her name was.

Cue to her screaming "What is my name? What is my [expletive] name?" on a busy street in Denver to him. Awkward!

The quick break.

Unsplash | Eric Ward

"This conversation took place on the 5th of July at a Ruby's Diner in Southern California at 7:30 PM...

Me: So, today we've been together 3 months huh?

Her: Yup.

Me: What do you think...wanna shoot for 3 more?

Her: Nah.

Me: Yeah, I think I feel the same way...

We're still friends...she's an awesome girl." - u/vietbond

The MySpace breakup.

Unsplash | Christin Hume

"I dated this girl for a week, then sent her a MySpace message saying "you + me = breakup" lol. Alternatively, we had dated a second time and I declared my singleness in a MySpace bulletin. That was when MySpace was cool." - u/Brainstream420

The grade school breakup.


Most of us have an awkward childhood relationship to look back on. This includes mall dates and awkward hand-holding.

Well, this girl found out that she and her bf broke up when he told her on IM a month later that he had moved to a different state.

The sushi date.

If you're going to break up with someone, make sure it's at an appropriate place and time.

This Redditor had a front-row seat to a guy breaking up with this girl at a sushi restaurant WHILE telling her he was cheating on her. Cue the drama.

The pickup.

"My sister broke up with her boyfriend in the school parking lot, as we waited for our mom to pick us up. Well, he didn't take it well, and when my mom arrived and we got in the car, he literally jumped on her hood and crawled along the car to the passenger's side window, begging her to reconsider. The school resource officer had to drag him away crying and screaming Weezer lyrics at my sister." - nicoles40e5cb895

The sickness.

When this guy's girlfriend was sick, he drove 100 miles to bring her soup, flowers, and a card. But when he pulled up, he saw her holding hands with another guy... He gave the presents to the guy and told him, "I was her bf, treat her well."

The daddy.

Unsplash | Bernard Hermant

“This couple was arguing – very loudly at that – about their problems in the relationship. Well one thing led to another and then a woman screams out: 'Oh yeah? WELL I [expletive] YOUR DAD!' The poor guy didn’t even know what to say. He was so dumbfounded that he just sat there while she stormed out.” - u/Italipinoy95

The tree.

"I broke up with my boyfriend in a park, and he LITERALLY CLIMBED UP A TREE to cry up there. I didn't really know what to do...so I just waited around for him to come back down." - strasbourg1518

The Venmo request.

Unsplash | Michael Longmire

When this girl was visiting her friend from college, her boyfriend wouldn't leave her alone. So she eventually blocked him to get some peace.

Well, he didn't like this as he sent her a Venmo request for the amount of the bill of their last dinner.

The rejected proposal.

This next one proves that public proposals are the worst.

This Redditor helped a guy plan the perfect proposal only for the girlfriend to TURN DOWN the proposal. Since he thought the tears were tears of joy, he even snapped some pics.

The secret relationship.

Unsplash | Christian Lue

"When I was a sophomore in high school, I was pretty good friends with this one guy. Well, one day I was reading in one of the classrooms when he walked in and broke up with me. Apparently, he thought we'd been dating for a year...and I had no idea." - Emily.e908

The parent trap.

Unsplash | Tyler Nix

This girl broke up with a guy after two months. Seems fine and all, right? Well, they later found out that their parents were secretly dating each other... Good thing they broke up, no?

The amusement park.

Unsplash | Kelly Sikkema

Remember how we talked about finding the right place and time to break up with someone?

Well, this Redditor witnessed a couple breaking up in line for an amusement park ride! The worst part is, they had a young son who was oblivious to this.

The farewell song.

When this girl broke up with a guy in college, he was crying and saying that he was going to change. At that very moment, her roommate started blasting Taylor Swift's "We Are Never Getting Back Together," which made him cry even harder.

The sting.

"My boyfriend was breaking up with me over the phone, and I was doing a great job of holding it together...until I STEPPED ON A GIANT WASP, barefoot! Needless to say, I totally lost my [expletive] after that. I was yelling and crying for the rest of the phone call...but for entirely different reasons." - khaleesi1313