Truly Heinous Breakups

February 6, 2024 | A.V. Land

Truly Heinous Breakups


Ah, romance…One minute it’s all "crazy in love" and then, in the blink of an eye, someone’s getting a late-night text that says, "Welcome to Dumpsville. Population: You". 


1. So I Married A Psychopath

My aunt and uncle went through fertility treatments for years before she finally got pregnant. They seemed so happy, we never saw it coming.

A couple of days after the baby arrived, my uncle drove my aunt and the new baby home from the hospital. As he was helping them up the front stairs, he turned to his wife and did the unthinkable.

He said, "Well, I don’t want to hang around and get attached to this baby. Bye!" He took off, leaving his poor wife standing there dumbfounded. We later found out that my uncle had three young daughters in another state with a different woman.

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2. Definitely Not A Soft Landing

My father-in-law had a girlfriend who broke up with him in Paris…on Valentine’s Day. But that wasn't even the worst part. They still had to fly back to America sitting right beside each other on the plane.

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3. It’s All In The Timing

I was unceremoniously dumped after seven years in the relationship. It was only later that I discovered the dark truth. According to acquaintances, she had been cheating on me. Strangely enough, though, the "best" part is that the dumping took place right after I had paid for not only her eldest son’s tuition coverage at college but also a massive vet bill.

It turns out that she had planned on dumping me earlier, but she had no way to pay these unexpected bills—and of course she wasn’t going to ask him to help so early into their new relationship.

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4. The Seven-Month Itch?

Eight months into my marriage, I came back from a girls’ weekend with my sister and cousin to find a shocking scene. The entire apartment was empty. Everything was gone—including most of my stuff. There was no note, no phone call, nothing.

It turned out that he wanted a divorce. At least he ended up giving me most of my stuff back after I asked for it.

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5. It’s Definitely Complicated

I'll never forget when my brother's crazy girlfriend changed her relationship status to "in a relationship"... with a guy who was obviously not my brother.

I called my brother because I was shocked that a) they had broken up and b) she had moved on so quickly. When I asked why they broke up, his response shook me.

He said, "We didn’t". He then called her and the other guy answered her phone and told my brother to back off. I wanted to kick her teeth in.

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6. Why You Gotta Be So Mean?

I was new to California and didn’t have many friends, but with some luck, I found myself in a relationship. It was six months in, and I started feeling pretty sick with pain, dizzy spells, and other fun (gross) stuff. So, I booked a doctor’s appointment with my new health insurance. The night before my appointment, I got some bad news.

I learned that my grandfather had been admitted to the hospital with heart problems. It was a major bummer. I loved the bejesus out of him, but he was in New York and I was poor. I tried to stay strong and headed to my appointment. While there, I was told that I likely had an issue that would lead to infertility, so I had best get the ball rolling on some tests.

Feeling pretty devastated about this and my grandpa’s current state, I called my boyfriend and asked if I could come over after work for comfort. His shocking answer was just the crummy cherry on top. I was coldly told no because he had a date with someone else. Awesome.

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7. Mi Casa IS NOT Su Casa

One Tuesday, there was a small fire in the office where my friend’s wife works. Because of that, she decided to go home for lunch and to await the all-clear call on her cell. When the wife got there, she was greeted by a disturbing sight. She found her husband’s secret "bit on the side" taking the wife’s clothes out of the closet and putting a bunch of her clothes in.

My friend had intended on telling his wife that their marriage was over that very evening. Unfortunately, the whole plan fell apart when his ditzy lover thought that the coast was clear to move her stuff in. In my humble opinion, arranging for your homewrecking lover to kick your wife out of her own house is the ultimate bad etiquette. 

Apparently, the judge thought so, too. My friend was taken to the cleaners—and deservedly so. However, that wasn't the best part of the story. As an extra dose of karma, his new lover left him the day after the judgment was rendered. Turns out she was only interested in the house, which, of course, he lost in the proceedings.

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8. Do You Think They’ll Notice?

My dad told me this story about his former boss who, one day, found his wife’s lifeless body. But it was what happened afterward that sent chills down my dad's spine.

The very next day, the assistant this man had been having an affair with was wearing his wife’s clothes, shoes, perfume, and jewelry. They tried to act like everything was normal. They even kept inviting my dad and mom to dinner, which they always declined for fear of being slain.

A couple of years ago, my dad went to a guitar convention and this ex-boss was there (they’d all worked in a music chain together) and recognized my dad. My dad told me he was still super scared of the guy. To top it all off, this dude was still with the same assistant.

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9. They Go Low, She Goes High

I was planning on breaking up with my live-in boyfriend because things had been going downhill for quite some time. That night, I came home and when I walked into our bedroom—and made the most infuriating discovery.

I caught him in bed with a good friend of mine. I was shocked but more relieved than anything—he was her problem now. Unfortunately, it was my bedroom and I needed to get my stuff out of there.

I walked over to the closet and pulled out all of my clothes. Then I went to the dresser and cleared out everything else that mattered to me. The whole time I did this, she was sitting there, in the buff, in my bed. I wasn’t angry, sad, or mad at her. 

I politely said, "I just need to get my stuff". She never left. She moved in that day. He ended up marrying her and is still married to her, even though she now cheats on him all the time, has multiple children with OTHER men, and isn’t welcome in our circle of friends because she’s cheated with the husbands.

Surprisingly, she’s hyper-Christian and extremely controlling to boot. I actually feel kinda bad for my ex.

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10. How Did It Even Last That Long?

I have two children from a previous marriage and one child with my now ex. I took a trip home (to another country) to see my eldest son graduate. With this trip, my spouse, who bitterly hated it when I traveled without him, urged me to "Take some extra time and see your friends".

Hmm…Historically it had been anger before I left, anger when I was gone, and anger when I got home. This man had been unemployed for nine years and was totally dependent on me and wanted for nothing. I got him every new toy, new computer, new car, new laptop, and all the video games. He would spend hours mastering them.

It was a pleasant surprise to be offered a bit of time for myself with no guilt. It felt good. He even seemed interested in the details of my son’s graduation…the day, the time, etc. I honestly thought nothing of it. But in retrospect, the red flags were flying right in front of my face.

On graduation day, as we were standing outside for the pictures, my ex texted me from 2,700 km (1,700 miles) away: "I want a divorce". Here I was posing for pictures while mentally rearranging travel plans so we could get home as soon as my son’s party was done. 

When I returned home, the house had been ransacked and anything of value had been taken. It looked like a tornado had gone through the living room. There was no note, no address, nothing. And he took my youngest with him. The icing on the cake, though, was a brochure he left on the nightstand. 

It was a brochure for partners of people who had been victims of mistreatment. The brochure described how these people could find ways to cope with what happened to their partners. This was his parting shot: Even though I had been a victim years before, HE was the one who suffered. 

Like everything else in life, hindsight reveals all. This man was the biggest passive-aggressive piece of work in the universe.

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11. Don’t Mess With Momma Bear

I’ve been through some bizarre breakups, but there is definitely one that stands out above the rest. After being together for two years, my college boyfriend decided to break up with me the night before my birthday, while at my mom’s house, as we were all having dinner together. 

We were just starting in on a fancy meal she made when he broached the topic in front of everyone. I could not believe that he chose that time and place to lay that on me. 

We ended up having a heated conversation in the kitchen as my mom graciously but awkwardly went to "check something in the other room" so that we could have some privacy. Unfortunately, it gets worse. About an hour and one ruined birthday meal later, he goes out to his car to leave. 

I was in the kitchen crying with my mom when he came back into the house because his car wouldn’t start. He rolls his eyes when he sees that I’m upset and says he needs a jump. After about 40 minutes, it becomes apparent that the car needs more than a jump start.

He looks at me and says, "So, I guess I’ll just crash on the couch". My mom and I were shocked by the suggestion at this point, but we have that good old Canadian politeness. We went to the kitchen to talk while he kicked up his feet in front of the TV. 

After a while, I reveal to her that lately he’s been screaming at me and physically intimidating me and that I had actually been wanting to end things with him. Without missing a beat, my mom did something that still shocks me

She grabbed a frying pan, walked into the living room where he was now dozing off, and bashed him over the head with it. She told him that she’s always thought he was a little idiot and he didn’t deserve me or any woman. She then screamed at him to get out of her house before she hits him again.

My mom’s a tiny, good-humored Christian woman, so this was super out of character. It was definitely the most decisively aggressive and, I’m sorry, hilarious thing I’ve ever seen her do. He was dumbfounded. He called us crazy and stormed out. The kicker? He was apparently STILL too cheap to call a cab or tow truck, so he slept in his car in our driveway.

The next morning, I had to knock on his window and help push him out of the driveway so my mom could drive me home. Clearly, I really missed out on a winsome gentleman right there.

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12. Tragedy + Time = Comedy

During high school, I went out with this girl for a brief time. There happened to be a big dance and I was not going to be able to go because of work. My girlfriend ended up going with a group of friends. I ended up getting a call from HER best friend saying that my girlfriend didn’t want to date me anymore.

To make matters worse, the next day at school I ended up finding out that she broke up with me so that she could make out with some guy AND the best friend who had called me. I was upset but realized there was nothing I could do. She ended up begging me to get back with her and I did for a week until I realized I was an idiot.

Fast forward to five years later when my roommate and I were chillin’ and exchanging stories of the good ol’ days over a few brews. He started to tell me how in high school he got some girl to dump her boyfriend to make out with him and another girl. I’m like that’s messed up, but kind of funny. Then it hit me…It turns out he was the guy!

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13. Ouch!

For almost a year, I was enjoying a pretty solid relationship—but then, out of nowhere, everything changed. Suddenly, my girlfriend had no time for me. She was always too busy, sometimes for weeks at a time. I was cool with this new development and just did my own thing for a while. 

Then, one day she canceled a date that we’d planned weeks in advance. This time I did get a little upset. We had an argument on Facebook chat in which she ended up telling me that she wasn't sure that she felt the same way about me as she used to. The next day, I got a Facebook message telling me it was over. 

When I asked if she’d at least break up with me face-to-face, she flat-out said no. When I asked why, she said she never really loved me. She also said that she didn’t want me to try to change her mind. A few weeks later, she started posting on Facebook about how she hates men. 

I hadn’t spoken to her since the breakup, but I had to figure this out. I asked around and finally unearthed the heart-wrenching truth: She’d been cheating on me with her ex. Apparently, things didn’t work out with him (again). Serves ya right.

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14. A Real Doozy

My high school sweetheart and I decided to try and have a baby. Before you judge, part of the reason was that I had been diagnosed with a disease that affected fertility and only worsened with age. After a couple of miscarriages, it worked and I gave birth to a baby boy. I was 20 and the father was 21. We planned on getting married. Unfortunately, things took a dark turn.

We were young, but old enough to be parents and we both made decent money. There were problems with the delivery and our son ended up with cerebral palsy. He was severely disabled and spent a lot of time in the hospital. We even moved to a different province, away from all of my family but closer to my boyfriend’s dad, to get better care for him.

I was responsible for our son’s care and my boyfriend worked. He barely even visited us in the hospital because he said hospitals bothered him. One day out of the blue, he sat me down to have a talk. He said he had figured out a way to solve all of our "problems". At first, I was excited—at least until he gave me a horrifying ultimatum…

He told me to give our son up for adoption or move out with him. Before he even had a chance to do anything, I simply packed up all my belonging, grabbed my son, and got the heck out of there. I had four more years with my son before he passed at the age of five. I never once regretted my decision.

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15. Ah, Young Love

It was the end of the summer and I was about to start high school, but my girlfriend was a year behind me so she was going to still be in middle school. I’m guessing she wanted to break it off with me before school started, but I never saw it coming. We were sitting on our mutual friend’s couch when she did it.

Both of our parents were pretty conservative and didn’t think we were old enough for dating, so we hung out at our mutual friend’s house a lot because his parents were more progressive and didn’t seem to have a problem with our young love. That said, his mom always seemed to be just around the corner whenever we were alone in a room.

Anyway, there I was—completely oblivious and enjoying her company—when she dropped the most devastating truth bomb on me. While still holding on to my hand, she whispers, "We’re breaking up". Then she swung her free hand and punched me as hard as she could in my crotch. 

I fell to the floor in pain as she stormed off while my friend just sat there laughing like a hyena.

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16. Wait For It

I was talking on the phone with my (then) fiancée, and at about 10:30 pm I heard a knock on the door on her end. I asked who was there and she said, "No one. It must be someone knocking on the neighbor’s door". 

She ended the call shortly after that because it was late, but she hung up the phone without saying goodbye or anything. That's when I started to get a weird feeling in the pit of my stomach. I tried to call her back to find out what was going on, but she ignored my calls. 

Around 45 minutes later, she picked up the phone and, with a guy talking in the background, told me that it was not working out between us and our relationship was over. I was about to ask what the guy in the background was saying, but then I heard it…"Come on baby. Hurry up and strip down so we can do it on the kitchen counter".

When I asked her who that was, she said, "Hahaha, he’s just kidding". Click. The next morning, she blew up my phone. I couldn’t believe that she would try to apologize after our exchange the night before…and after she slept with him...and after he spent the night with her at her apartment. She was the poster child for "never date crazy".

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17. Surprise!

After 18 years of marriage, I became pregnant with our third child. Even though the pregnancy was unplanned, I expected my husband to be happy. I couldn’t have been more wrong. Despite our relative financial security, he totally flipped out at the news and gave me an ultimatum: abortion or divorce. He is now my very ex-husband.

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18. Better Than The Big Screen

The girl I was dating in my freshman year of college was always a little odd, but I was young and she was way out of my league, so I stuck around. She lived about an hour away from me, so when I did get to see her, she was always fairly mellow, but every now and then she’d say something kinda odd. Anyway, fast-forward six months…

During Christmas break, we went on a movie date. The theater was packed. About 10 minutes into the movie, she does the most random thing imaginable. She punched me as hard as she could. I dropped to the ground and she started this unholy screaming at me while kicking and punching me. 

I slowly stood back up and tried to talk to her, but she head-butted me.I was finally able to pin her arms behind her and drag her out of the theater. I called her dad to find out what the heck was going on. He said the worst thing the father of your significant other can say: "Oh no, she’s off her medication again". 

It turns out, she had a rather severe case of bipolar with a little manic depression thrown in. In the meantime, the theater had called the authorities to report a domestic disturbance. When the officers showed up, they saw me holding her and promptly tasered me. Then they tasered her because she started punching me again. 

Much later, I found out that she went at me because she didn’t like how I was looking at the actress on the screen.

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19. Majorly Mixed Messages

He started to cancel every other date with me for a period of several months. He would slowly increase the intervals between our dates making them further and further apart, but always assuring me how much he cared for me, he was just really busy. 

It’s important to explain that I was cool with this because of my noncommittal stance toward relationships at the time. But I had no idea my world was about to come crashing down.

Our setup of occasional shagging, dinner dates, and none-too-frequent conversation was basically my ideal romance. I considered myself to be madly in love with him. Now, fast forward through more than a year of him telling me that he loved me and would always be there if I needed him, etc. to the night after my cat perished.

I called him, trying to muffle my sobs, and explained that my cat had passed. I said that everything at my place reminded me of the cat and I couldn’t deal. "Could I sleep—just sleep—at your place?" He not only said no but proceeded to tell me how "needy" I was and then unceremoniously dumped me.

I didn’t grieve for him at all. I did regret every moment that I’d chosen to spend with him instead of my cat, who a) never made me talk about feelings and b) knew that needing cuddle time doesn’t exactly make a girl needy.

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20. Two-Timing Hubby

I spent eight years with my ex, who was my best friend in high school, but we never dated until we were 30. I had two young kids at that point. He raised them with me for those eight years. My youngest bonded more deeply with him, as their bio dad abandoned his role. 

He worked on a remote island the last two years of our relationship while I lived on the mainland and took care of our home, pets, and kids (I worked, too). We would take turns visiting each other. I found out he'd been seeing this bartender, proposed to her, and was living a second life on the island, all while we were trying to conceive. 

He didn't have the integrity to tell me himself. I had to find out through mutual friends. He'd been sleeping with both of us that entire time. The breakup was brutal, and my heart will never be the same. My kids lost a father figure, I lost my best friend, and he's now married to the bartender.

Crying woman in red long sleeve shirtAndrea Piacquadio , Pexels

21. At Least He’s Self-Aware?

I haven’t always been a good person. I was 15 at the time (this was 15 years ago) and my family was very poor. I was dating a girl whose family had a lot of money. She was always giving me a hard time about, complaining that I was cheap and couldn't buy her expensive gifts. 

After about four months of this, I started keeping track of all of the expenses incurred by our relationship. After I had a month’s worth of data, I printed out an expense statement, put all of her stuff in a cardboard box, and went to her house. I handed her my expenses and said, "We are over because I can’t afford to keep seeing you". 

Not surprisingly, that was pretty much the last time I spoke to her. I can’t believe I basically billed her.

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22. Poor Nat

My friend took his girlfriend to The Keg for a $100 dinner and then to the farmers’ market to shop for Christmas gifts. He proceeded to top off the night by watching a live performance of It’s A Wonderful Life. After driving her home, he parked outside her house and said, "Natalie, I’m sorry, but I’m breaking up with you".

Natalie screamed, threw her purse in his face, and sprinted off into the snow at 1:00 in the morning. He followed her footprints for about three km (two miles) to find her at her sister’s house. He could hear her weeping uncontrollably and dry heaving behind the house. He didn’t know what to do, so he went back to his car to get her purse to return it.

On the drive back, he saw her walking. However, when she saw him, she screamed and tried to run away again, but slipped in the snow. He went to help her but she screamed a third time and yelled at him to "Stay away!" Her sister, who was walking with her, said, "Natalie thought you were going to propose to her. She’s devastated. How could you do that?"

My friend then wrote a letter in his car explaining what had gone down, gave it to his now-ex’s sister, and drove home and went to sleep. He compares what he did that night to a wrestling move where you bring your opponent up to the very top rope and then bodyslams them down. This was his first long-term relationship and he is happily single three years later.

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23. That’s One Way To Get The Heart Pumping

I wasn’t the one broken up with but I was accidentally the cause. I met this really cute girl and we started talking and seemed to hit it off. She invited me over because she was "looking for a friend with benefits". Anyway, we were in the middle of doing the bedroom rodeo when it turned into my worst nightmare.

Her boyfriend suddenly walked in—he was never previously mentioned. He looked super upset, which was understandable considering at that moment I was inside his girlfriend. I quickly grabbed my clothes and got the heck out of there. As I was getting myself together in the hallway of their apartment building, several people were staring because he was really loud.

She then gets kicked out of the apartment and he yelled, "We’re done!" It was probably the most embarrassing thing that ever happened to me, but I have no shame. You see, that wasn't the last time I saw her. OF COURSE, I continued sleeping with her for a few more months. So, in a way, it was all worth it.

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24. Definitely Five Stars

My girlfriend went on a family vacation to Dubai. While she was there, she unceremoniously dumped me in the weirdest way possible: by FAX from the hotel they were staying in. The best part was when I got a second fax from the hotel staff a little later saying that they were sorry for me and wished me luck finding someone who would treat me better than she did.

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25. Spidey Senses

After two decades of marriage, I got this unsettling feeling that my husband wasn't being loyal to me. I tried talking to him about it but he remained pretty closed off, so I resorted to hacking into his email (to my shame). I was able to get into it but found nothing. I also tried to get into his phone but by then he was literally sleeping with it.

Finally, after calling him on his fake sweat stains from playing ball hockey (I’m sure there were balls involved, no doubt, but no hockey) and asking why he was never at the places he said he was (I would get a friend to drive me to look for our car), he finally confessed. He said, "I love you and will always love you, but I am not in love with you anymore".

So one month shy of our 21st wedding anniversary, he confessed that there was someone else. The weird thing about the moment was that I had two simultaneous thoughts run through my head. One was, "My worst fear has happened". The other was, "Oh, thank God I won’t have to sleep with him anymore". He is now married to the other woman.

They are about to have their first wedding anniversary—how time flies. Anyway, he’s happier now and I am, too, so I guess I should really write them a thank you note. Ha…

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26. U-Haul It Out Of There

He ended it after 10 years together, four of those living together. I called him to see what he wanted to do for dinner and kept getting his voicemail. I called his secretary, and she said, "Oh, he should be on his flight by now". She quickly figured out I didn’t know what she was talking about, so she told me in the nicest way she could that he went to Vegas. 

I left work to go home immediately—and when I got there, my jaw DROPPED. I found that the locks had been changed and there was a U-Haul truck. He had packed everything I owned up in the truck after I had left for work, then flew to Vegas with his friends for the weekend. He left me a note saying he was sorry.

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27. A Real Thrill Ride

I witnessed this at an amusement park. A guy and a girl were arguing. Well, the girl was upset and the guy was just trying to calm her down because she was starting to cause a big scene. But it got so much worse. Suddenly, the girl screeched, "YOU ARE THE BIGGEST REGRET OF MY LIFE!" right in the guy’s face.

I'll never forget the destroyed look on the poor guy's face. My heart broke for him. After the despair passed, he became apoplectic for a minute, and then, in a voice dripping with quiet rage, he told the girl to leave and then stormed away.

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28. How Could You?

My girlfriend of three years broke up with me because she had ovarian cancer. She said she didn’t want me to have to deal with her issues from chemo and that she’d never be able to have kids. Sounds selfless, right? WRONG.

I later found out that she now has two kids and is pregnant with a third. The true story is that she left me for another guy because he enabled her heavy drinking while I tried to curb it.

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29. She Has Some Nerve

In my story, the kicker isn’t so much the way I was dumped (I walked in and found him with another girl during a party at his place), but the way the new girl behaved. She had the nerve to call me the next day and say, "Hi, I’m still at (now ex-boyfriend’s) place and I was just wondering…Did you leave any tampons here?"

Girl, what? You’re now sleeping with the boy who was the love of my life for the past three years, in a bed that was practically mine, and you’re using the mugs, furniture, and spare pajamas that I’d used for three years. Seriously, what more do you want from me? My clothes? My parents? You’re definitely not getting my tampons.

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30. A Wild Ride

I was returning to her after my summer internship ended. I'd spent five long days driving to her and she decided to break up with me in front of ALL her friends and family. I then got the joy of another long drive back home. That was a wonderful combination of mental exhaustion from 35-ish hours of recent driving and a head full of messy emotions. But that wasn't the worst part.

This breakup occurred in Canada, and my phone battery was depleted, which made navigation almost impossible. Did I mention that we’re still great friends? Having had some time to decompress, I now realize the breakup was for the better. Did I mention the conversation with the border guard was awkward? He said, "She’s not in the trunk, is she?"

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31. You Never Forget Your First

This happened with my first girlfriend ever. She was my first kiss, my first time, my first everything. I was so crazy in love with her, that I would do anything for her. I should also mention that I was also only 15 at the time so bear with my foolishness. I worked my butt off for an entire summer to make enough money to buy her a $1,500 engagement ring. Little did I know, things were about to go downhill.

That night, I brought it home and asked her if she’d marry me when we turn 18. She said yes. One week later, I couldn't get a hold of her all day on Saturday. On Sunday, I finally got her on the phone and she told me through text that all-day Saturday she had been shagging her ex-boyfriend and now she was breaking up with me.

Five years later, I got a wild idea to see if she has a Facebook. When I found her page, I saw that not only was she married to the guy she cheated on me with, but she was also holding their baby in her arms in the profile pic. I zoomed in on the photo and guess what ring is on her finger? I hope she gets hit by a bus.

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32. You Think You Know Someone

My older sister married this guy after dating him for four years. But sadly, after three years together, things took a nasty turn. He admitted that he had been cheating on her from the time they started dating. What’s worse is that he gave her this devastating news when she was eight months pregnant and the very next day she lost the baby.

We never found out what went wrong with her pregnancy, but to put a cherry on top of the bad relationship, he told her he wanted to stay married but see other women, too. Obviously, the divorce process didn’t take long. I was proud of her for standing up for herself, and I can’t believe how she managed to overcome her loss.

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33. Karma Came For Him

We were doing long distance for a few months while I was getting ready to move to where he lived. I had friends and family there, too, so the move wasn't solely based on him. He was pretty religious, whereas I'm not religious at all, and I had looked past our differences because I was young (stupid) and he was unreasonably hot. 

His dedication to his religion also made me think he'd have strong morals and that I could trust him (again, I was 18 and stupid). A couple months before I was set to move, I paid to fly across the country to spend my birthday with him. 

He took me out for a romantic dinner—and that's when he made a confession that blindsided me. He proceeded to tell me that he had slept with a friend of his and needed space to "get right with god". Me, him, and Jesus had a really awkward drive back to where I was staying, then he and I obviously broke up.

We were catching up over Facebook a couple years ago, and I learned he'd lost all his hair, was working in a medicine job, and was stuck an unhappy marriage. Hearing that honestly made me believe in god a little bit.

Young man in military uniform is praying.RDNE Stock project, Pexels

34. Once Bitten

Back in high school, I was in a relationship with a girl who was way out of my league. I must admit, it felt pretty good knowing that even though every guy wanted her, she was mine. We spent hours on end just hanging out together. It was the closest I had ever been to someone. I thought we were definitely in it for the long haul. BOY was I wrong.

Anyway, on the day of my graduation party, my dad was talking to her and he said something about how it wouldn’t be difficult for the two of us to still date while I was off at college. To which she replied, "We’re not dating". It was the most awkward experience to be told by my father that we were never dating—despite the fact that she told me she loved me.

That was many years ago,  though. I have been with a wonderful woman for the past four years now, and I couldn’t be happier. However, I make it a point to check in with her to make sure that she is still my girlfriend from time to time LOL.

Heinously Heart-Wrenching BreakupsPexels

35. Now, That Took A Turn

A friend of mine dated a girl named Amy. She had a twin sister named Betty. My friend dated Amy for about a year before they got engaged. The day before the wedding, Amy made a stunning confession. She told him that her name was really Betty and he had actually been dating Betty for the last 10 months. Wait for it…Apparently, Betty fell in love with Amy’s boyfriend.

Since Amy was thinking of breaking it off with her guy (my friend) anyway, they decided to switch places. My friend fell in love with Betty thinking she was Amy and he proposed. When "Amy" confessed to the deception, she cried and apologized profusely. My friend loved her so much that he told her that he didn’t care what name she went by he still wanted to marry her.

They have been together for three years.

Heinously Heart-Wrenching BreakupsPexels

36. Ouch!

My sister had been dating this guy for four years. However, by the time their relationship was ending, she was barely seeing him, and his excuses were downright pathetic. He would say things like he didn’t have enough gas to get to her place or he was caught up at uni with some project. 

It got to the point where they only saw each other about once every two weeks. To make matters worse, when they did see each other, he’d only stay for an hour and would spend most of it passed out on the couch. Eventually, she decided to call him out on his BS. His response? 

"Look, you’re not the axis of my life. I need more space and these days I hardly have time to paint my Warhammer figurines". He then proceeded to break up with her—over MSN. The guy was 25 years old at the time and getting a degree in pharmaceuticals. 

Shortly after this, we heard news that he’d started a forge in his basement to mass produce more Warhammer models, and a few months later, he moved to Russia chasing after a mail-order bride. I wish I was making this up.

Heinously Heart-Wrenching BreakupsFlickr, Dan Foy

37. Good Riddance!

When my husband of almost 20 years decided to leave me and the kids, he told our then-15-year-old daughter about his plan a whole two weeks before he told me—and made her keep it a secret. But it gets even worse. When he told me, it was in a very matter-of-fact way, and he then started whistling a little tune and demanded to keep living with us for the next two weeks.

Not only that, he even wanted to keep sleeping in my bed while he closed on his new condo, which I also knew nothing about. After a couple of days, as he was getting ready to go to work, I strongly suggested that maybe he’d like to go to a hotel. He did not go quiet.

After packing his back, he made a scene—waking up the kids by screaming, "I'M LEAVING!! MOMMY KICKED ME OUT! DON'T FORGET THAT!"

Heinously Heart-Wrenching BreakupsPexels

38. Kick Them When They’re Down Much?

I became ill at his work's going away party and when I had to leave early, he got upset with me and said, "We’ll talk about this later". I went home, laid down, and woke up a few hours later in even worse pain. My mom eventually convinced me to go to the hospital. I ended up staying there for a week. But that was only the beginning of the nightmare.

During that time, his mother came to visit me, but he didn’t. He eventually made an appearance—two hours after I was discharged. When we got to my place, my mom asked him to go pick up my prescriptions. He not only threw a fit when I said I was in too much pain to go with him but he also flat-out refused to go if I didn’t join him. I needed my painkillers, so I ended up accompanying him.

Now, I had a GIANT incision due to a slow leak. It had apparently traveled, so I had a 15 cm (six-inch) wound. It hurt to walk, breathe, and make sudden movements. He kept grabbing my arm and muttering that I wasn’t moving fast enough. When we finally got out of the store and back home, he looked at me, a wide smile on his face, and he asked me to go down on him.

I felt terrible, I was on antibiotics, I was in pain with a large incision and drain in me, and I just wanted to sleep. I could not believe that he had the nerve to ask me for that. When I told him no, he threw a fit, told me I was no fun and dumped me.

Heinously Heart-Wrenching BreakupsPexels

39. Destination Wedding Debacle

We had plans to attend a destination wedding months in advance. I was dumped before the wedding. As I never met those getting married, I backed out of being the plus one and requested a refund—a clean break. I was begged to reconsider and she was able to convince me. This gave me hope that she wanted things to work, as did I. Turns out, I was terribly mistaken.

After a week of vacationing on a tropical island, I was friend-zoned for the first time in nineteen (19) months at the couple’s destination event celebrating commitment and love. Ordinarily, I couldn’t keep her off me, but she was distant and cold in a way I never experienced from her.

The next morning I learned most of her girlfriends—except the bride—understood we were broken up. When I asked why the bride was out of the loop, it was “none of her business” even though the bride and groom made it our business that another couple didn’t make it because they had broken up. 

I felt so disrespectful and regretted that I didn’t follow my instinct and back out for a clean breakup. The universe spoke when she came down with COVID and I didn’t 2k+ miles from home. Even so, I paid half to extend our trip while I cared for her. I cooked for her, catered to her, and spent hours on the phone with her keeping her company as she quarantined. 

It felt like we were a couple again! Unconditional love brought us close again, but I was abandoned and blocked shortly thereafter. I started wondering what I ever meant to her in the first place. I felt so played, used, and gross. Why would you take a fresh ex to a destination wedding just to fill a seat with no desire to be with them!?

I self-isolated for months and hardly spoke to anyone, as I examined my self-worth and shattered heart. That twice-served rejection was painful on many levels. I considered spending my life with her, but I was left feeling like I didn’t even know who she was.

Gloria Swanson factsPixabay

40. No Good Deed Goes Unpunished

My mom is beautiful, thin, young, smart, hardworking, and kind. Her husband is 20 years older and she thought he would be honest and mature after she had been mistreated in past relationships. She's never been so wrong. 

Welp, the hideous old guy was diagnosed with a type of stage 4 cancer that people RARELY survive, and he underwent two different types of chemo treatment. She wiped his wrinkly behind, changed his diapers, shaved his back, flushed his catheter, fed him meds—EVERYTHING. 

She was even a team captain for Relay for Life in his honor. He was given a second chance at life and decided to use it on a seven-month affair, which my mom ended up discovering. After he was found out and mom forgave him, he was so "stressed" by her not trusting him that he left without a word for three weeks and went to live at his other house.

She’s filing for divorce this month. I could not be happier.

Heinously Heart-Wrenching BreakupsPexels

41. That Took A Turn

In this story, I am the offender of the bad breakup. I was in college and my then-girlfriend was at a different college. I had a feeling she was cheating and wanted to break up. I decided to get loaded and go through with it. I started with a phone call (pathetic, I know) but I just couldn’t do it. Then she sent me a pic of her and some guy in bed.

Infuriated, I replied with mean texts and a pic of me hooking up with a girl. I finally ended up passing out and woke up the next day to a lot of missed phone calls and messages. As I read them, I was horrified. She was not cheating—that guy in the bed was ME. Ugh, I broke up because a girl cheated on me with me.

Heinously Heart-Wrenching BreakupsFreepik,wayhomestudio

42. That Did Not Go Well

I was once dating a girl who lived on the other side of the city, which was 100% a car town so there was no good public transport. Anyway, after a whole day hanging out at my place watching films and fooling around, I decided to break up with her. Unfortunately, it was late at night and what little public transport there was had ended.

I don’t drive and my mom was in a cast so we couldn’t get her home. My now-ex sat in my room crying for 40 minutes while she waited for her mom to come and pick her up. I sat downstairs playing video games trying to ignore it all while my mom stood there shaking her head in disappointment. Yeah, I was awful.

Heinously Heart-Wrenching BreakupsPexels

43. Thanks For Nothin’

After helping my boyfriend immensely with his small business, I then helped him move into a new apartment. Once all his stuff was moved in, he turned to me and said, "Yeah, I kind of want to get acclimated to my new living space, so I don’t think we should see each other anymore".

I made him drive me home instead of taking the 40-minute transit ride. What a douchecanoe.

Heinously Heart-Wrenching BreakupsPexels

44. Fairytale Of New York

I was 21 and she was 18. We met at a department store in Manhattan where she lived with her parents. After dating for a week, I picked her up at her home, and got the usual, though pleasant, interrogation from her mom and dad. You know, questions like, "how old are you?" and "what do you do for a living?" I even got the half-joking "This guy’s a keeper".

A few days later, she told me that she was almost 18, which didn’t sound so bad. Then a bit later, she admitted the horrifying truth. She was 16. I started to freak out a bit, but then thought, "Well, if her parents were okay with it…" She finally explained that she was ALMOST fifteen years old! Needless to say, I immediately explained why we couldn’t see each other again. Ever.

What kind of parents are OK with that kind of situation? Also, who lets a 14-year-old wander around Manhattan all by themselves?

Heinously Heart-Wrenching BreakupsFreepik, cookie_studio

45. Be Careful Out There

I found out from a coworker that the cute blonde who came to eat lunch with me every day had matched with him on Tinder. Unfortunately, she was my fiancée. I decided to make a fake account and ended up matching with her. I talked to her for a week on the app—and her messages had been very X-rated and she was down to meet.

It was time for my plan to fall into place…As myself, I made plans for us for Friday. Then fake me made plans with her for the same Friday. She called the real me and gave me some lame excuse to cancel our plans. Six years gone down the drain.

Heinously Heart-Wrenching BreakupsPexels

46. You Can’t Make This Up

My boyfriend went to a bar with some coworkers, picked up a flight attendant, went to the airport hotel with her, and then took her to breakfast. After he broke my heart with this confession, I asked why he took her to breakfast. His reply? "I didn’t want to be the guy who just leaves after".

Apparently, he thought it was totally fine to cheat on his girlfriend of three years, though. Cool.

Heinously Heart-Wrenching BreakupsPexels

47. Don’t Mix Business With Pleasure

A friend of mine started a business with the girlfriend he was seeing. During this time, they had some money problems. He took a short-term but high-paying job over the summer to make some money for them to live off of. He flew halfway across the world for this job. While he was over there, he crushed his hand while working.

As he’s being wheeled into surgery, he calls his girlfriend to let her know that even though he was hurt, he’d made the money that they needed. She told him that she had a new boyfriend, that their business was done, and she hated him for "not having his act together". The saddest part of this story is that he’s a great guy.

As his friend, it really sucks to see him blowing all the money he worked so hard for on booze. My friend has a drinking problem because he can’t deal with the fact that some people just suck that much. He’s told me a few times he’d like to end his life. I beg him not to, and I wish there was more that I could do to help him.

Heinously Heart-Wrenching BreakupsPexels

48. Highway To The Danger Zone

Thankfully, I still lived with my parents during this time or it would have been extremely difficult for me to get out as this guy was legitimately crazy. I made the mistake of breaking up with him while we were in the car and he started driving into oncoming traffic because "If I can’t have you, no one can!" I was forced to take the breakup back so that I could make it home alive.

Once I was safe, I broke up with him again over text. He took an entire bottle of Tylenol and called me to tell me that he was ending his life because of me. I called paramedics and they went to get him. After he was released from the hospital, he cut his wrists and sent me a picture of what I was "doing to him". I called the paramedics again.

He was involuntarily committed to a psych ward, but after he was released, he stalked me everywhere I went. I wanted to get a restraining order, but my mom wouldn’t let me because she thought he loved me and that I should give him another chance. After a couple of months, he just suddenly stopped following me and it was finally over.

Heinously Heart-Wrenching BreakupsPexels

49. Cool, Calm, And Calculated

I ruined his life in one day. As I waited for him to get home from holidays with his other girlfriend, I packed up all of his things. When he got back, I asked him if there was someone else, to which he, of course, replied, "No". I then told him all his stuff was packed and ready to go and opened the Uber app and asked, "Which friend do you want to stay with?"

He tried to ask if he could pick his stuff up later, but I refused. I also took his keys. Then I put on my detective hat and found his other girlfriend. I showed up uninvited at a party she was attending and told her all about my relationship with him. Not surprisingly, she immediately broke up with him after hearing me out.

To this day, I’m so proud of how I handled it. He ended up single and living with a friend for a while. I planned it well so that he didn’t have a chance to lie or escape. He had been cheating on me for one year before I discovered it. I ended up forgiving him and moving on because I didn’t want hatred to consume me. I deserve better.

Heinously Heart-Wrenching BreakupsPexels

50. White Lotus Season Three?

My friend and his girlfriend invited me on a three-day weekend getaway. Not wanting to be a third wheel, I invited my platonic female friend to join us. That turned out to be a huge mistake. My friend ended up breaking up with his girlfriend within hours of the four of us arriving at the hotel—and he did it in front of all three of us. She was crushed yet she still had to spend the entire weekend with him.

The next day, things got even worse. He proceeded to hook up with the friend I had invited. Right in front of his now ex. The poor girl was just trying to recover and save any shred of dignity she still had. It was, without a doubt, the most awkward weekend of my life. I spent the whole time comforting her and giving her a shoulder to cry on while he proceeded to throw his hookup in our faces.

I think Karma worked its magic, though. It has been five years since that weekend and he’s single, miserable, and depressed. He hasn’t had a steady relationship in years and she is happily married.

Heinously Heart-Wrenching BreakupsPexels

51. He Should Have Added "Population: You"

My coworker told me the wild story about how he broke with his long-term girlfriend. It was BRUTAL. They met for a date, drank too much, slept together, and when she passed out, he took a marker and wrote "Welcome to Dumpsville" on her forehead.

She totally deserved it, since she had been cheating on him for months. He just wanted to sleep with her one last time.

Heinously Heart-Wrenching BreakupsPexels

52. Shameful Split

I'll never forget getting dumped on the way to my boyfriend's bowling night. But it gets worse. Not only did he crush my heart but he told me to WAIT IN THE CAR while he spent the evening bowling. I was a total idiot because I thought he'd be coming straight back to drive me home. NOPE.

I waited for two long hours, just to have him come out of the bowling alley flanked by his cousins. They were all happy and laughing until they spotted me in the car, puffy-faced and crying. It was truly awkward.

Heinously Heart-Wrenching BreakupsFreepik,freepik

53. Savage

I work for an airline and my coworker found out that his girlfriend was cheating on him. He didn’t let on to her that he knew and instead told her that he wanted to go on vacation. They flew to Japan and checked into the hotel. Once she was asleep, he went back to the airport, canceled her ticket, and then flew home leaving her stranded in Tokyo with no money.

Heinously Heart-Wrenching BreakupsPexels

54. All About The Long Game

While I was in the army, I walked in on the most heartbreaking scene: my girlfriend and my army buddy going at it. They didn’t notice me, so I backed out quietly and didn’t let on that I had seen them. The next day, we were embarking on a 10-hour drive to her parents’ house for the Fourth of July weekend. It was hard for me but during the drive, I acted as if nothing happened.

When we were halfway to her parents’ house, we stopped at a highway rest stop so she could pee. When she was in there, I took all of her bags out of the car, left them on the pavement, and took off. I drove back to base with the biggest grin on my face. I got some really interesting voicemail messages from her. Boy, was she miffed.

Heinously Heart-Wrenching BreakupsPexels

Sources: Reddit, Quora, Buzzfeed


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