January 16, 2024 | A.V. Land

The Most 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". After reading about these cruel breakups, the only thing rawer than your emotions will be the comforting cookie dough you’re shoveling into your mouth.

1. So I Married A Psychopath

My aunt and uncle experienced years of fertility treatments before they finally welcomed a baby. My uncle drove his wife and their newborn home from the hospital. But as he was helping them up the front stairs, he did something no one could have expected.

He said, "Well, I don’t want to hang around and get attached to this baby. Bye!" Then, he just left, leaving his bewildered wife standing there. We later discovered that my uncle had three young daughters in another state with another woman.

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2. Definitely Not A Soft Landing

My father-in-law was dating someone who ended their relationship in Paris...on Valentine's Day. And to make it even more awkward, they had to sit next to each other on the plane back to America.

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3. It’s All In The Timing

I was unexpectedly left after being in the relationship for seven years. Later, I learned through some acquaintances that she had been unfaithful to me. But oddly enough, the most striking part is that this breakup happened right after I had covered not only her eldest son’s college tuition but also a huge vet bill.

It seems that she had intended to break up with me earlier, but she faced these unexpected bills and didn’t have a way to pay them—and of course, she wasn’t going to ask him for help so early in their new relationship.

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4. The Seven-Month Itch?

After being married for eight months, I returned from a weekend trip with my sister and cousin to discover something incredibly surprising. The entire apartment was completely empty. Everything had disappeared, including a majority of my belongings. 

I didn't find any note, receive a phone call, or any kind of explanation. Eventually, I found out that my spouse wanted a divorce. Thankfully, when I requested it, they returned most of my belongings.

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5. It’s Definitely Complicated

My brother’s girlfriend updated her status to "In a relationship," but the guy wasn’t my brother. I rang up my brother, surprised that a) they had split and b) she had moved on so fast. When I inquired about their breakup, he was like, "ummm...We didn’t". Then he phoned her. 

The other guy picked up and told my brother to back off. I was so mad, I felt like giving her a piece of my mind.

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6. Why You Gotta Be So Mean?

When I first moved to California, I didn't have many friends. But luckily, I started dating someone after a while. We were together for about six months when I began experiencing some unpleasant symptoms like pain, dizziness, and other not-so-fun stuff. 

So, I decided to make an appointment with a doctor covered by my new health insurance. The night before my appointment, I received some unfortunate news. My grandfather had been hospitalized due to heart problems. This was really disappointing for me because I cared a lot about him, but he was all the way in New York and I couldn't afford to visit him. 

Despite this, I tried to be strong and went ahead with my doctor's appointment. During the visit, I was informed that I might have a condition that could cause infertility. They suggested I start doing some tests to get a better understanding of the issue. 

Feeling devastated by this news and concerned about my grandfather's health, I called my boyfriend and asked if I could come over after work for some comfort. Unfortunately, he responded coldly and told me he had a date with someone else. Needless to say, this was not the response I was hoping for.

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7. Mi Casa IS NOT Su Casa

It was a typical Tuesday when a small fire broke out at the office where my friend’s wife worked. Because of this, she decided to head home for lunch and wait for the all-clear call. When she arrived, she walked into quite a shocking scene. 

She found her husband’s secret girlfriend taking her clothes out of the closet and replacing them with her own! My friend had actually planned to tell his wife their marriage was over that very evening. But, his whole plan unraveled when his clueless lover assumed it was safe to move her stuff in. 

Personally, I think having your secret girlfriend try to move your wife out of her own home is just about as low as you can go. Seems like the judge agreed. My friend really got what was coming to him in the settlement. But the real kicker? His new girlfriend left him the day after the judgment. 

Turns out, she was only after the house, which, of course, he lost in the proceedings.

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8. Do You Think They’ll Notice?

My dad once shared this tale about his old boss, who had come across his wife's lifeless body. The day after, the assistant, who he’d been having a secret relationship with, started wearing his late wife’s clothes, shoes, perfume, and jewelry. 

They acted as if everything was normal and kept inviting my parents over for dinner, invitations my folks always turned down, fearing for their safety. A couple of years back, my dad bumped into this former boss at a guitar convention (they had all worked in a music chain together), and my dad admitted he still felt pretty uneasy around the guy. 

To add to the strangeness, the guy was still together with that same assistant.

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9. They Go Low, She Goes High

I had been thinking about ending things with my boyfriend, with whom I was living, as our relationship had been on the rocks for a while. One evening, I returned home to find him in bed with a close friend of mine. Although I was taken aback, I felt more relieved than anything else—it was like he was her issue now. 

However, it was still my bedroom, and I needed to retrieve my belongings. I headed to the closet and gathered all my clothes, then moved to the dresser and collected everything else important to me. All the while, she remained there, unclothed, sitting in my bed. 

I didn’t harbor any anger or sadness towards her. I simply said, “I just need to get my stuff.” She never left and moved in that very day. He eventually married her, and they’re still together, despite her continual infidelity, having children with different men, and no longer being welcome among our friends due to her liaisons with their spouses.

Interestingly, she’s notably religious and quite controlling. I actually feel somewhat sorry for my ex.

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10. How Did It Even Last That Long?

I have two kids from a previous marriage and one with my now ex. I went back to my home country to attend my eldest son's graduation. Usually, my spouse, who really disliked it when I traveled alone, would get upset, but this time, he encouraged me to "Spend some extra time and see your friends". That was unusual. 

Typically, there’d be anger before I left, while I was away, and when I returned. Despite being unemployed for nine years and fully dependent on me, he always had the latest gadgets, cars, and video games, spending hours enjoying them. So, having a bit of guilt-free time for myself was a nice change. 

He even seemed curious about my son’s graduation details, which I didn’t find suspicious. But on the graduation day, as we were taking photos, I received a terrible text from him, miles away: "I want a divorce". There I was, trying to smile for pictures and mentally reorganizing travel plans to get home right after my son’s celebration.

 When I did return, the house was a mess, valuables were gone, and it looked like a storm had hit our living room. There was no note, no address, nothing. And he had taken my youngest child with him. But what topped it all off was a brochure he left on the nightstand. It was for partners of SA victims, suggesting ways to cope with their partner’s experiences.

This was his final message: Despite me being an SA victim years ago, HE was the one who suffered. Looking back, it’s clear that he was incredibly passive-aggressive.

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11. Don’t Mess With Momma Bear

I’ve had my share of unusual breakups, but one definitely takes the cake. My college boyfriend of two years chose to break up with me the night before my birthday, at my mom’s house, right in the middle of dinner. I couldn’t believe he picked that moment to drop the news. 

A heated conversation ensued in the kitchen, with my mom giving us privacy by "checking something in another room". An hour and a ruined birthday meal later, he was ready to leave but discovered his car wouldn’t start. Seeing me upset, he rolled his eyes and asked for help. After 40 minutes, it was clear his car needed more than a jump.

“So, I guess I’ll just crash on the couch,” he declared. Stunned but polite, my mom and I left him to discuss in the kitchen. I confided in her about his recent aggressive behavior and my desire to end things.

To my surprise, my usually mild-mannered mom grabbed a frying pan, confronted him, and told him off, saying he didn’t deserve me or any woman, and demanded he leave. It was so out of character and, I must admit, quite funny. He called us crazy and left but, being too frugal for a cab or tow truck, slept in his car in our driveway.

The next morning, I had to help push his car out of the driveway so we could leave. Clearly, I hadn’t lost a gem of a guy there.

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12. Tragedy + Time = Comedy

Back in high school, I briefly dated a girl. There was a big dance, and since I had to work, I couldn’t attend. She went with a group of friends, and out of the blue, her best friend called me to say that my girlfriend didn’t want to date me anymore. But there was a twist. 

The next day at school, I found out she broke up with me to make out with some guy and the very same best friend who had called me. Though I was upset, I knew there was nothing I could do. She eventually pleaded for us to get back together, and foolishly, I agreed for a week before realizing my mistake.

Fast forward five years, my roommate and I were reminiscing about the past over a few drinks. He began sharing a story about how he convinced some girl to dump her boyfriend in high school to make out with him and another girl. I initially found it funny but messed up, and then it dawned on me… He was that guy...

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13. Ouch!

For almost a year, my relationship was going strong, but then out of nowhere, my girlfriend started being too busy to hang out—for weeks on end. I took it in stride and spent some time doing my own thing. However, when she canceled a date we’d planned weeks ahead, I got a bit upset.

We had a disagreement over Facebook chat, and she admitted she wasn’t sure she felt the same way about me anymore. The next day, she sent me a Facebook message ending things. When I requested a face-to-face breakup, she outright refused. When I questioned why, she made a heartbreaking confession. 

She said she never really loved me. She also made it clear she didn’t want me trying to change her mind. A few weeks later, she began posting on Facebook about her disdain for men. I hadn’t spoken to her since the split, but I needed to understand. Upon asking around, I discovered she’d been seeing her ex behind my back. 

It seems things didn’t pan out with him (once again). Well, karma’s a thing.

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14. A Real Doozy

My high school sweetheart and I decided to try for a baby, partly because I was diagnosed with a condition affecting fertility that would worsen over time. After a couple of losses, we were blessed with a baby boy when I was 20, and he was 21. We had plans to marry, but sadly, things didn’t go as we'd hoped.

Though young, we were both earning decently and felt mature enough to be parents. However, complications during delivery resulted in our son having cerebral palsy. He was severely disabled and required frequent hospital stays. To ensure better care for him, we relocated closer to my boyfriend’s dad but away from my family.

I handled our son’s care while my boyfriend worked, but he rarely visited us, claiming hospitals unnerved him. Unexpectedly, he proposed a solution to our "problems" that left me shocked. He presented me with an awful ultimatum—either give our son up for adoption or move out with him. 

Without hesitation, I packed up our things and left with our son. We had four more precious years together before he passed at five. I’ve never regretted choosing my son.

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15. Ah, Young Love

It was the close of summer, and I was gearing up for high school, but my girlfriend was a grade below, so she'd still be in middle school. I guess she wanted to end things before the school year began, but I didn't see it coming. We were at a mutual friend’s house, sitting on the couch when it happened.

Our parents, being quite conservative, didn’t really believe we were old enough to date. So, we spent a lot of time at our friend’s place—his folks were more relaxed and didn’t mind our youthful relationship. That being said, his mom was always subtly nearby whenever we were alone.

So there we were, just holding hands on the couch, when out of the blue, she turned to me and announced, "We’re breaking up". Next thing I knew, she had swung her free hand and landed a punch. I doubled over in pain as she stormed out, with my friend left chuckling in the background.

That day remains etched in my memory. She not only broke my heart but left me quite literally hurting.

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16. Wait For It

I was having a phone chat with my then-fiancée, and around 10:30 pm, I heard a knock on her end. Curious, I asked who it was, and she replied, "No one. It's probably someone at the neighbor's door". She ended the call shortly after, without even saying goodbye.

Concerned, I tried to call her back to understand what was happening, but my calls went unanswered. Roughly 45 minutes later, she answered, and I could hear a guy talking in the background. She told me things weren’t working out between us, and our relationship was over. Just as I was about to inquire about the guy, I heard him say, "Come on baby. Hurry up so I can kiss you".

When I confronted her about the guy’s voice, she laughed it off, saying, "Hahaha, he’s just kidding". Then, click, she hung up. The next morning, she inundated my phone with calls. I was baffled that she’d try to apologize after what happened the previous night—especially after being with that guy and him staying the night at her place.

 That experience taught me a valuable lesson about being cautious with whom you date.

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17. Surprise!

After being married for 18 years, I found out I was pregnant with our third child, even though it wasn't planned. I thought my husband would be happy, but I was completely mistaken. Despite us being financially stable, he had a major negative reaction to the news. He gave me an ultimatum: either get an abortion or get a divorce. Now, he's my ex-husband.

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18. Better Than The Big Screen

In my freshman year of college, I dated this girl who was a bit unusual, but I was young, and she seemed way out of my league, so I stayed. Living an hour away, our meet-ups were infrequent, and she was mostly mellow, albeit with occasional odd remarks. Fast-forward six months, we found ourselves in a movie theater during Christmas break.

It was a packed theater with a brand-new movie playing. About 10 minutes in, out of nowhere, she struck me hard. I fell to the ground, and she launched into a frenzied attack, screaming, kicking, and punching. Stunned, I managed to stand up and tried to calm her down, but she responded with a head-butt.

Finally, I restrained her and dragged her out of the theater, immediately calling her dad to understand what was happening. He uttered the words you never want to hear from a partner’s parent: "Oh no, she’s off her medication again". As it turned out, she was dealing with a severe case of bipolar disorder, accompanied by manic depression.

Meanwhile, the theater had alerted the authorities about a domestic disturbance. When they arrived and saw me holding her, they tasered me. Then, when she resumed her attack, they tasered her too. I later learned that her outburst was triggered by the way I was looking at the actress on the screen.

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19. Majorly Mixed Messages

For several months, he began canceling every other date with me, slowly making our meetings less and less frequent. However, he always assured me he really cared, and that he was just super busy. It’s crucial to mention that I was okay with this, given my casual approach to relationships at the time. Little did I know, my world was about to turn upside down.

Our arrangement of occasional intimate encounters, dinner dates, and infrequent conversations was pretty much my ideal relationship. I considered myself head over heels in love with him. Fast forward through more than a year of him assuring me of his love and support, especially on the night after my cat passed.

Distraught, I called him, trying my best not to break down, and shared that my cat was gone. Everything at my place reminded me of my furry friend, and it was too much to bear. "Could I just sleep at your place?" His response was not only a ‘no,' but he went on to label me "needy" and then broke up with me on the spot.

I didn’t mourn the loss of the relationship. However, I did regret every moment I opted to spend with him rather than my cat, who a) never demanded emotional talks and b) understood that desiring comfort doesn’t make someone needy.

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20. He Should Have Added "Population: You"

My colleague shared an interesting story about how he broke up with his girlfriend of two years. They went out on a date, had a bit too much to drink, ended up spending the night together. While she was asleep, he decided to play a harmless prank and wrote "Welcome to Dumpsville" on her forehead with a marker. 

I guess he felt it was justified because she had been cheating on him for several months. He just wanted to have one final, intimate encounter with her.

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21. At Least He’s Self-Aware?

I used to be a different person in the past. This happened when I was 15, around 15 years ago. Back then, my family was really poor and I was dating a girl whose family was wealthy. She would constantly give me a hard time about it, always complaining that I couldn't take her out or buy her things. 

This went on for about four months until I decided to start keeping track of all our relationship expenses. After a month of collecting data, I printed out a statement of all the expenses and put all her belongings in a box. I went to her house and handed her the expenses, telling her that we were breaking up because I couldn't afford to continue seeing her. 

Not surprisingly, that was pretty much the last time we spoke. It's hard to believe that I basically invoiced her.

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22. Poor Nat

My buddy treated his girlfriend, Natalie, to a fancy $100 dinner at The Keg and a festive shopping spree at the farmers' market. They wrapped up the evening with a live show 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".

Stunned, Natalie screamed, tossed her purse at him, and ran off into the snowy night. He followed her tracks for about two miles, eventually finding her at her sister’s house, where he could hear her sobbing and upset. Unsure of what to do next, he decided to go back to his car to retrieve her purse.

On his way back, he spotted her walking. Upon seeing him, she screamed and tried to escape again, but slipped in the snow. He approached to help, but she yelled, "Stay away!" Her sister, accompanying her, revealed, "Natalie thought you were going to propose. She’s devastated. How could you?"

Feeling the weight of the situation, my friend penned a letter in his car explaining everything, handed it to Natalie's sister, and headed home. He likens his actions that night to a wrestling move—lifting your opponent up high, only to slam them down hard. That was his first serious relationship, and three years later, he's happily single.

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

I wasn't the one who got dumped, but I unintentionally caused the breakup. I met this really attractive girl and we hit it off. She invited me over because she wanted a casual relationship. While we were in the middle of being intimate, things took a turn for the worse. 

Unexpectedly, her boyfriend walked in, even though she never mentioned him before. Naturally, he looked really upset since I was with his girlfriend at the time. I quickly gathered my clothes and left in a hurry. As I was getting myself together in the hallway of their apartment building, people were staring because he was making a scene.

 As a result, she got kicked out of the apartment and he shouted, "It's over between us!" It was incredibly embarrassing for me, but I ended up continuing to sleep with her for a few more months, so it wasn't all terrible.

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24. Definitely Five Stars

My girlfriend took a trip with her family to Dubai. Unfortunately, during her stay there, she chose to end our relationship by sending a fax from the hotel. What made it even more surprising was receiving another fax from the hotel staff, expressing their sympathy and hoping that I would find someone who treated me better than she did.

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25. Spidey Senses

After two decades of marriage, I began sensing my husband might be involved with someone else. I tried discussing it with him, but he kept things to himself, leading me (regrettably) to snoop into his email. While I didn’t find anything there, I couldn’t access his phone as he kept it close.

My suspicions grew when I noticed inconsistencies in his stories and whereabouts. I even had a friend help me check on his locations by looking for our car. Eventually, he admitted, "I love you and will always love you, but I am not in love with you anymore".

Just a month before our 21st anniversary, he disclosed that he was seeing someone else. Strangely, I felt a mix of relief and realization of my worst fear. Part of me was actually relieved that I wouldn’t be intimate with him anymore. He's now married to the other woman, and they are approaching their first anniversary.

Time indeed flies. He seems happier, and truth be told, so am I. Maybe I should send them a thank you note. Ha!

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26. A Real Thrill Ride

I saw this happen at an amusement park. There was a couple arguing—the girl was really upset and causing a scene, while the guy was just trying to calm her down. But then things took a turn for the worse. Out of nowhere, the girl screamed right in the guy's face, "You are the biggest mistake of my life!" 

The guy's expression changed completely, and it was truly heartbreaking to see how devastated he looked. Once he got over his despair, he got really angry for a moment and then, in a tense and angry tone, he told the girl to leave him alone and stormed off.

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27. How Could You?

My girlfriend of three years ended our relationship because she was diagnosed with ovarian cancer. She didn't want me to go through the hardships of supporting her during chemotherapy, or face the reality that she may not be able to have children in the future. However, I later discovered that she has two children now and is expecting a third. 

In truth, she left me for another guy who encouraged her excessive drinking, while I tried to help her control it.

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28. She Has Some Nerve

In my story, what really shocked me wasn't how I got dumped (I walked in on my now ex-boyfriend with another girl at his party), but how the new girl acted afterwards. 

Believe it or not, she had the audacity to call me the next day and ask, "Hey, I'm still at (now ex-boyfriend's) place and I was just wondering... Did you happen to leave any tampons here?" Seriously, what on earth? 

You're now sleeping with the guy who I've been in love with for the past three years, in a bed that practically belonged to me, and you're using the mugs, furniture, and spare pajamas that I used for three years. What more could you possibly want from me? My clothes? My parents? Well, you can forget about getting my tampons.

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29. A Wild Ride

I had just finished my summer internship and was heading back to her after a five-day drive when she decided to end things—right in the middle of a gathering with her family and friends. Then, I had the pleasure of making that long drive back home, juggling mental exhaustion from around 35 hours of driving and a whirlwind of emotions.

To top it off, the breakup happened in Canada, and my phone was out of battery, making navigation a real challenge. Did I mention we managed to stay good friends? After some time to reflect, I’ve come to see the breakup was actually a good thing. Oh, and did I bring up the awkward conversation with the border guard? 

He jokingly asked, "She’s not in the trunk, is she?"

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30. You Never Forget Your First

This story dates back to my first-ever girlfriend—my first kiss, my first love, my first everything. I was head over heels for her and would have done anything to make her happy. Bear in mind, I was only 15, so I had a lot to learn. I worked tirelessly all summer to save up enough to buy her a $1,500 engagement ring, unaware that things were about to take a turn.

Excitedly, I presented the ring and asked if she'd marry me when we both turned 18. She agreed. However, a week later, I couldn’t reach her for an entire day. When I finally got through to her the next day, she texted me that she’d spent Saturday with her ex-boyfriend and was now ending things with me.

Five years down the line, curiosity led me to check if she had a Facebook account. There she was, not only married to the same guy but holding their baby in her profile picture. And guess which ring was on her finger? While it stung, I hope she’s learned since then and wish her well.

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31. You Think You Know Someone

So basically, my older sister married this guy she had been dating for four years. Unfortunately, after three years of marriage, things took a terrible turn. He confessed that he had been cheating on her since they first started dating. 

What's even more heartbreaking is that he dropped this bombshell on her when she was eight months pregnant, and tragically, the very next day she lost the baby. We never figured out what caused her pregnancy complications, but to add insult to injury, he had the audacity to tell her that he wanted to stay married but also see other women. 

Obviously, it didn't take long for them to get divorced after that. I was really proud of my sister for standing up for herself and I can't believe how she was able to overcome such a devastating loss.

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32. Once Bitten

In high school, I dated a girl who was really popular. It made me feel good knowing that she chose to be with me, even though lots of guys wanted her. We spent a lot of time together and became really close. I thought we would be together for a long time. But then, on the day of my graduation party, my dad mentioned to her that we could still date when I went off to college. And she said, "We're not dating". 

It was really awkward because she had told me she loved me. That happened a long time ago though. Now, I've been with an amazing woman for the past four years and I'm really happy. Although, every once in a while, I jokingly check in with her to make sure she's still my girlfriend.

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33. Now, That Took A Turn

So, my friend was dating this girl named Amy who happened to have a twin sister named Betty. They were together for about a year before getting engaged. The day before their wedding, Amy dropped a bombshell. She confessed that her real name was Betty and she had been pretending to be Amy for the past 10 months.

Turns out, Betty had actually fallen in love with Amy's boyfriend and was considering ending things with him. So, they came up with this crazy plan to switch identities. My friend unknowingly fell for Betty, thinking she was Amy, and popped the question. When Betty finally came clean about the whole deception, she was really upset and apologetic. 

But my friend was so in love with her that he didn't care what name she went by—he still wanted to marry her. Fast forward three years and they're still happily together.

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34. All About The Long Game

While I was serving in the army, I accidentally walked in on my girlfriend and my army buddy being intimate. They didn't realize that I saw them, so I quietly left without revealing that I had witnessed anything. The next day, we had a long 10-hour drive ahead of us to her parents' house for the Fourth of July weekend. 

It was difficult for me, but I acted as if nothing had happened during the journey. When we reached a rest stop halfway to her parents' house, she went inside to use the bathroom. While she was away, I decided to take all of her bags out of the car and left them on the ground. Then, I drove back to the army base with a big smile on my face. 

I received some interesting voicemail messages from her, and boy, was she angry.

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35. Ouch!

My sister had been dating this guy for four years. Towards the end of their relationship, she started seeing him less and less, and the reasons he gave were pretty weak. He would say things like he didn't have enough gas to come to her place or that he was too busy at uni with some project. It got to the point where they only saw each other about once every two weeks. 

To make things even worse, when they did get together, he would only stay for an hour and spend most of that time sleeping on the couch. Eventually, my sister decided to confront him about his excuses. His response was pretty ridiculous. 

He basically said, "Look, you're not the center of my life. I need more space, and these days I hardly have time for my hobbies, like painting my Warhammer figurines". Then, out of nowhere, he broke up with her through a messaging app. Keep in mind that this guy was already 25 years old and studying pharmaceuticals. 

Shortly after the breakup, we found out that he had set up a forge in his basement to make more Warhammer models, and a few months later, he moved to Russia to pursue a relationship with a mail-order bride. I wish I was making this up.

Heinously Heart-Wrenching BreakupsFlickr, Dan Foy

36. Good Riddance!

When my husband decided to leave me and our children, he chose to tell our 15-year-old daughter two weeks before informing me. He insisted she keep it a secret, which was upsetting. But it gets worse. When he eventually told me, he did so in a very matter-of-fact manner and then started whistling a tune. 

He even had the audacity to demand that he continue living with us for the next two weeks. To make matters even more uncomfortable, he wanted to keep sleeping in my bed while he completed the purchase of his new condo, which I had no knowledge of. 

After a few days, when he was getting ready for work, I strongly suggested that he find a hotel to stay in temporarily. As a result, he packed a bag and woke up the kids by shouting at the top of his lungs, claiming I had kicked him out.

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37. Kick Them When They’re Down Much?

I got sick during a party for his work and had to leave early. He got upset and said we'd talk later. When I got home, I felt even worse and my mom convinced me to go to the hospital. I ended up staying there for a week. His mom came to visit, but he didn't. He finally showed up two hours after I was discharged. 

When we got to my place, my mom asked him to pick up my prescriptions. He threw a fit when I said I was too much pain to go with him, and he refused to go if I didn't come too. I needed my painkillers, so I ended up going with him. But here's the thing—I had a huge incision because of a slow leak. 

The wound was 15 cm (six inches) long and it hurt to walk, breathe, or make sudden movements. He kept grabbing my arm and complaining that I wasn't moving fast enough. Finally, when we got back home from the store, he smiled and asked if we could be intimate. 

I felt awful—I was on antibiotics, in pain from a big incision and a drain inside me, and all I wanted was to sleep. I couldn't believe he had the nerve to ask me that. When I said no, he threw a tantrum, called me boring, and broke up with me.

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38. No Good Deed Goes Unpunished

My mom is a beautiful, thin, young, smart, hardworking, and kind woman. She believed that her husband, who is twenty years older, would be honest and mature, especially after her past experiences in relationships. But, unfortunately, she was completely wrong. Well, this older guy turned out to be incredibly awful. 

He was diagnosed with a type of stage 4 cancer that very few people survive. He had to go through two different types of chemotherapy for treatment. During this difficult time, my mom went above and beyond to take care of him. She did everything from wiping his wrinkly behind, changing his diapers, shaving his back, flushing his catheter, to making sure he took all his medications. 

She even became a team captain for Relay for Life, all in honor of her husband. But guess what? After getting a second chance at life, he decided to have a seven-month affair. Can you believe it? My mom eventually found out about it. Even after she discovered his affair, my mom forgave him. 

However, instead of appreciating her forgiveness, he got all "stressed" because she didn't fully trust him. So what did he do? He disappeared without a single word for three weeks and went to live at his other house. Thankfully, my mom has finally had enough. This month, she is filing for divorce. And honestly, I couldn't be happier about it.

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39. Shameful Split

My ex broke up with me while we were in his car on the way to his family's bowling night. He left me waiting in the car while he played, and I thought he would join me soon after making an excuse to his family. But no, I ended up waiting for two whole hours! Finally, he came out of the bowling alley with his cousins and saw me there, all puffy-faced and crying. It was a really uncomfortable and awkward situation.

Heinously Heart-Wrenching BreakupsFreepik,freepik

40. Savage

I work for an airline, and my coworker recently discovered that his girlfriend was being unfaithful. Instead of confronting her, he cleverly decided to plan a vacation together. They boarded a flight to Japan and settled into a hotel. After she fell asleep, he quietly made his way back to the airport, cancelled her ticket, and caught a flight back home, leaving her in a tricky situation all alone in Tokyo with no funds.

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41. That Took A Turn

In this story, I was responsible for the breakup. I was in college while my girlfriend was attending a different college. I had a suspicion that she was being unfaithful, so I decided to end the relationship. I made the unfortunate choice to have a few drinks before following through. 

At first, I tried to break up with her over the phone (which looking back was pretty pathetic), but I couldn't bring myself to do it. Then, she sent me a photo of her in bed with another guy. This really angered me, so I responded with hurtful texts and even sent her a picture of me being intimate with another girl. 

Eventually, I ended up falling asleep and woke up the next day to discover numerous missed calls and messages. As I read through them, I was absolutely horrified to realize that the person in bed with her was actually me. I had broken up with her over a misunderstanding, thinking she cheated on me with myself. It was such a frustrating situation.

Heinously Heart-Wrenching BreakupsFreepik,wayhomestudio

42. That Did Not Go Well

I used to date a girl who lived on the other side of the city, where there wasn't good public transportation because everyone relied on cars. One day, we spent the entire day at my place watching movies and goofing off. But by the end of the day, I realized I wanted to break up with her. 

The problem was that it was late at night and public transport had already stopped running. I didn't have a car, and my mom couldn't drive her home because she was in a cast. So, my now-ex-girlfriend sat in my room crying for about 40 minutes while she waited for her mom to come and pick her up. 

Meanwhile, I stayed downstairs playing video games, trying to ignore the situation. My mom stood there, disappointed in me. Yeah, I definitely acted like a jerk.

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43. Thanks For Nothin’

After providing a lot of assistance to my boyfriend with his small business, I also helped him with the process of moving into a new apartment. Once we finished moving his belongings, he turned to me and said, "You know, I think I need some time to adjust to my new place, so maybe we shouldn't see each other anymore".

Instead of taking the 40-minute transit ride, I asked him to drive me home.

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44. Fairytale Of New York

I was 21 and she was 18 when we first met at a department store in Manhattan. She lived there with her parents. After dating for a week, I went to pick her up from her home. Her mom and dad asked me the usual questions like how old I was and what I did for a living. They even made a half-joking remark that I was a keeper. 

A few days later, she told me something shocking: she was almost 18. At first, it didn't seem too bad. But then she confessed the horrifying truth—she was actually 16. Needless to say, I immediately explained that we couldn't continue seeing each other. Not ever. What kind of parents would be okay with a situation like that? And who allows a 14-year-old to wander around Manhattan alone?

Heinously Heart-Wrenching BreakupsFreepik, cookie_studio

45. Be Careful Out There

I found out from a coworker that the attractive person I used to have lunch with every day had connected with my coworker on Tinder. The problem was, this person was my fiancée. So, I came up with a plan. I created a fake profile on the app and matched with her. 

We chatted for a whole week, and her messages were very explicit, hinting that she was open to meeting up. Finally, it was time to put my plan into action. I, as myself, made plans with her for Friday. At the same time, my fake profile made separate plans for the same day. 

On Friday, she called me, the real me, and came up with a weak excuse to cancel our plans. It was a devastating moment, as six years of a relationship went down the drain.

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46. You Can’t Make This Up

So here's what happened: My boyfriend decided to head out to a bar with his coworkers. While he was there, he ended up meeting and hitting it off with a flight attendant. They eventually ended up at an airport hotel together and even had breakfast in the morning. I was completely devastated when he confessed all of this to me.

Naturally, I asked him why he took her to breakfast, hoping for some sort of explanation. His response was, "I didn't want to be the kind of person who just leaves after". Clearly, he didn't see any problem with cheating on me, despite us being together for three years. Pretty disappointing.

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47. Don’t Mix Business With Pleasure

One of my friends decided to start a business with his girlfriend. Unfortunately, they ran into some financial troubles during this time. In order to make some quick money for them to live on, he took a well-paying but temporary job over the summer. This job required him to travel to a faraway place. 

While he was there, he had a terrible accident and injured his hand. Just before going into surgery, he called his girlfriend to let her know that despite his injury, he had managed to earn the money they needed. Shockingly, she told him that she had found a new boyfriend, ended their business, and even expressed anger towards him for not being "more organized". 

The saddest part of this whole story is that my friend is truly a great person. It really hurts me to see him spending all the hard-earned money he made on his drinking habit. He has developed a drinking problem because he struggles to cope with how some people can be so terrible. 

He has even confided in me that he has thought about ending his own life. I plead with him not to do that, and I wish there was more I could do to support him.

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48. Highway To The Danger Zone

Luckily, I was still living with my parents at the time, or else it would have been really tough for me to escape from this guy who was genuinely crazy. I made the mistake of breaking up with him while we were in the car, and he started driving recklessly into oncoming traffic, saying that if he couldn't have me, no one could. 

I had to take back the breakup just to ensure my own safety. Once I was in a safe place, I ended things with him again through a text message. He reacted by taking a whole bottle of Tylenol and phoning me to say that he was going to end his life because of me. I immediately called for help, and paramedics came to his aid. 

After being released from the hospital, he proceeded to hurt himself and sent me an inappropriate photo, claiming that I was responsible for his actions. I called the paramedics once more. He was eventually admitted to a psychiatric ward against his will, but even after his release, he continued to stalk and follow me everywhere I went. 

I wanted to obtain a restraining order, but my mom wouldn't allow it because she believed he still loved me and that I should give him another chance. However, after a few months, he mysteriously stopped pursuing me, and finally, it was all over.

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49. Cool, Calm, And Calculated

I completely turned his life upside down in just one day. While he was away on a holiday with his other girlfriend, I packed up all of his belongings, waiting for him to return. When he finally came back, I confronted him about whether or not there was someone else in his life. 

Naturally, he denied it, saying there was no one else. That's when I dropped the bombshell—everything was packed and ready to go, and I even had the Uber app open, asking him which friend he wanted to stay with. He tried to negotiate picking up his things later, but I stood my ground and refused. I also took his keys, leaving him with no choice. 

Then, I took on the role of a detective and tracked down his other girlfriend. I showed up uninvited at a party she was attending and spilled all the details about my relationship with him. It didn't come as a surprise when she immediately broke up with him after hearing everything. To this day, I feel a sense of pride in how I handled the situation. 

He ended up single and crashing with a friend for a while. I had planned everything meticulously, ensuring he couldn't lie or escape. He had actually been cheating on me for a whole year before I discovered the truth. In the end, I decided to forgive him and move forward because I didn't want hatred to take over my life. I truly deserve better.

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50. White Lotus Season Three?

My buddy and his girlfriend invited me to go on a weekend trip with them. I didn't want to feel like a third wheel, so I asked a female friend (who I'm just friends with) to come along. Well, that turned out to be a big mistake. Shortly after we arrived at the hotel, my friend ended up breaking up with his girlfriend right in front of all of us.

It was really tough on her, but she had to spend the whole weekend with him. The next day, things got even worse. My friend ended up getting involved with the friend I had invited, right in front of his ex-girlfriend. It was terrible to witness her trying to recover and maintain her dignity. 

That weekend was definitely the most awkward experience of my life. I spent the entire time comforting her and being there for her while he flaunted his new fling in our faces. However, I think karma eventually caught up with him. It's been five years since that weekend, and he's now single, miserable, and unhappy. 

He hasn't had a serious relationship in years, while the girl he broke up with is happily married.

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