Twisted Dating Stories

October 16, 2023 | Jennifer McFarlane

Twisted Dating Stories

The spark of a new romance holds the promise of excitement and joy. But, as these Redditors share, sometimes romance takes a swift wrong turn into some uncomfortable, and downright frightening, territory. Read these astonishing stories to discover how a broken heart from a romance gone wrong can often be a blessing in disguise.

1. Hair-Raising Accident

I used to hook up with guys I’d meet online at this website called Craigslist. I was going through a really self-destructive phase of my life and that’s really all I have to say about that. One day, I connected with this one guy and we arranged to meet up. I was already on the way to his motel room when I get this weird text from him.

Clearly, the text was an accident. It was meant for someone else. The text showed a picture of me and it said something like “got a new toy for us this week”. I have no idea who the text was for but me and this guy were only supposed to hook up that one night only. After that, I sure as heck didn’t continue on to that motel.


2. No Hard Feelings

I was 22 years old, had a one-year-old kid and no social life, and was bored out of my tree. I had a brief and ill-advised flirtation with a co-worker. He had joined the Army, so I ended it a few weeks after he left for basic training. I broke it off mostly because I was still in the “do I even like you” phase of the relationship. He was already in the "let's buy a farm and have five kids" phase.

Three years later, he's back in town and runs into my sister at the gas station where she worked. He asked how she was doing and seemed perfectly pleasant. Then, he asked about me. She said I was fine. His response was chilling.

As reported by my sister, he said, "That's too bad, I hoped she was deceased. If I see that woman I'm going to run her over with my car". Then, he just turned around and left. Ooooooookay, psycho boy.

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3. Always Trust The Gut

Back in high school, I met a guy I clicked instantly with. Not only did he have the same birthday as my dad and my grandfather, but he was also left-handed, just like my dad and grandfather! In my mind, these were all obvious signs that we were meant to be. But, for some reason, every time he asked me out, I refused him.

Each and every time, I got this overwhelming weird feeling and simply could not say “yes”. Finally, this poor guy gave up and moved on. I kicked myself for the longest time for messing things up with my "soul mate". Then, he asked out my friend—and his dark side emerged.

On their date, he took her somewhere remote and got her high, and did some bad things to her.

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4. A Spider’s Web

I was chatting it up online for a few weeks with a female WAYYYY out of my league. It was nothing major, just chatting. One night, she actually contacted me first. There was lots of flirting from her and suggestive hints. Wow, I thought. This was the first time she had acted like that. And, I should add, this was late at night.

Then, she asked me to come over and see her. My alarm bells went off. I stalled, slowly playing her until she went to bed. Next morning, I hit her up. There was no answer. And there wasn't much convo between us either. A few weeks go by. She's on the news—and I can't believe my eyes.

She was setting up her dates and trying to rob them. One time, it all went bad. There were two deceased victims—the guy she set up and a guy on her team.

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5. As The Saga Turns

My very first girlfriend and I dated for about seven months. Even at the ripe age of 17, I truly “loved” her. We had plans to move interstate together. She moved first to secure the accommodation and I would follow a week later once I’d finished working. Two days after she moved, she blindsided me.

She tells me not to bother coming anymore because she’s met someone. I was devastated for a whole year afterward. She ended up marrying that guy and moved in with him and his best friend. They lived happily together for a few years, no issues with the marriage whatsoever. But that's not the end of the story.

One summer, my ex-girlfriend, her husband, and the housemate all decided to go on a three-week road trip together. Partway through, the husband gets called back to work and has to fly home. My ex and the housemate finish up the trip and return home.

Upon returning home together, my ex-girlfriend and the housemate make a big announcement. Apparently, spending so much time alone on the road trip, they had discovered their undying love for each other, and would henceforth be an item. The husband is understandably crushed. Join the club, buddy. At least he knows how I felt.

So, here’s the kicker. Not only did the three of them continue to live together, so the poor husband had to listen to them be together every night, but he and his housemate work in the same company, in the same cubicle, directly opposite each other.

I discovered all this when I took a job at that same company and heard the tale around the office. Since then, she and the housemate had a child. I’m eagerly awaiting the next chapter in the saga.

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6. Zoos Are Less Messy

He was my first love and it lasted nearly seven years. He actually wanted to leave me halfway through the relationship because I lost weight and wasn't fat anymore. That should have been my first clue. But anyways, last I heard he lives in the Virgin Islands with a great guy who takes care of everything. A sugar daddy, let’s say.

It’s all good except the house is rundown and they have a ton of ducks and lizards and tortoises. My ex is a bit of an animal hoarder. He got to be known as “the pet shop guy” and he really loved the notoriety, I guess. We had a small zoo back then. Multiple reptiles, snakes, and lizards. Fish, birds. You name it.

Well, apparently, my ex and his new man hooked up with some homeless dude when they were back in the States. This dude has issues and he ended up getting my ex hooked on illicit substances. My ex tried to get his partner to let the homeless guy live with them. Glad I got out when I did. I'm sure the island is nice.

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7. Heist Turned Out Well

She seemed really great, fun to be with and everything was a breath of fresh air. But the timing was bad because I was planning to move in three months. Still, we had a blast together in that short time. About a year later, we planned to meet up when she was in my area. On the weekend we were going to see each other, something weird happened.

A new girl I had seen a couple of times had her apartment trashed and I was helping her. We got a lot closer and I felt bad ditching her so I told the old girl I was busy. Turns out, the new girl is now my wife which is nice. The house getting broken into was a great twist of fate. Years later, I check Instagram to see what the old girl is up to.

I see her postings of affirmation videos, laying out all her struggles with mental health, anger, and self-destructive stuff. That’s fine, but included in that were descriptions of hard battles with addiction and serial lying to partners. She’s not a bad person, just in pain from early trauma with her mom, but I know I would’ve gotten hurt too.

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8. A Talented Lady

My story is “the one that got away and I didn’t know how I managed to escape that situation until  it somehow swooped around the world and I still got nailed”. I had a massive crush on one of my older brother’s friends in high school. She was an all-star field hockey player and an artist. For some reason my brother’s friends liked me and I could tag along to picnics and parties.

She would hang out with me like a babysitter when I was clearly out of place and we’d draw and sculpt. She taught me to play field hockey while everyone was drinking. I was 13 and she was 16. Fast forward 12 years and I’m at the beach for the weekend with my brother. His friends show up, including her.

Once again, a lot of drinking and we are the only people keeping it at a low simmer, preferring to swim, run on the beach, play frisbee, and handle the grill. One night, we were the last people standing and she put her head on my shoulder and said I made her weekend.

We ended up hooking up and she told me she was going to break up with her boyfriend back where she lived. It was news to me, but I thought, “Oh my goodness, the woman that I dreamed about is infatuated with me! Yahtzee!”

Eventually, we moved in together and got married, despite my brother, her sister, her mom, and her friends privately warning me to watch out, that she’s a “sneak". Then her true colors began to show.

It turns out she had a bad drinking problem. She was able to hide it because she was functional and good at concealing the actual amount she drank. She also cheated on me multiple times.

This lady was a total professional at lying. She was also very talented at living two separate lives at the exact same time. I never even suspected anything until five years into our relationship! I should have seen it coming. Everyone else did. Instead, I took that one straight in the heart.

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9. Pretty Bad Boy

I was in love with this guy during middle school and high school. I mean he was just GORGEOUS. We messed around a lot during that time and then, in twelfth grade, he got a girlfriend. He was serious about her and I was heartbroken. We were still cool with each other so I just chalked it up and thought it wasn't meant to be.

Fast forward to after high school. He joins the army and marries the serious girlfriend. Three years later, I was scrolling through a news app when I see a picture of his face. I read the article and was totally shocked. It was saying he was injuring females in the army housing neighborhood he and his wife lived in.

He had done horrible things to three separate women before they caught him. At the young age of 21 years old, this guy got himself sentenced to 65 years behind bars. All I could think of was how his poor wife must have felt. I also really wonder if she had a strange feeling about her husband around that time?

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10. Too Close For Comfort

I dated this guy in college and was madly, madly in love with him. I seriously thought he was “the one” I would marry. But his mother didn't like me. She felt so strongly that she worked on him. Little by little, she eventually convinced him to break up with me. I was heartbroken and devastated, to say the least. I could not get him out of my mind.

For six months, I emailed him a few times just to say hi. But the last time I do, I get a response FROM HIS MOM telling me to stop emailing her son. 20 years later, I’m on Linkedin and his profile pops up as a suggestion. Out of curiosity, I click on it. All joking aside, in his Linkedin profile, this guy is talking about his MOM more than a little bit. Yikes!

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11. A Date With Evil

Way back when I was a freshman in college, I dated this guy. He was tall, handsome, athletic. Seemed like a good catch. Our relationship was pretty casual, nothing too serious. After second semester, he went back home to be with his family. The funny thing was I wasn’t devastated about it. Him leaving didn’t bother me.

So, flash ahead a few years and there’s a huge story all over the news. And I’m talking major. It was on Dateline NBC, 20/20, news all over the country. Turns out this guy I dated briefly in college is Scott Peterson. He took his wife Laci's life and their unborn child. Finding this information was absolutely mind-blowing.

Twisted Dating StoriesUnsplash, Fa Barboza

12. Slightly Different Directions

When I was a freshman in high school, my first girlfriend was a sophomore. Score a point there. I was a short, skinny, white dude and she was a curvy, beautiful black woman. We dated for nine whole months. Of course, in my adolescent mind, I figured that meant she was “the one”. Then, out of the blue, she breaks up with me.

It was a big surprise because she dumped me to start dating a girl. No big deal, it just came as a surprise. A decade and some time later and I’m happily married to my wife and have three beautiful children. I was shocked to find out that my old high school girlfriend is sitting behind bars for an inappropriate relationship with a 14-year-old girl.

Twisted Dating StoriesUnsplash, Oswald Elsaboath

13. Matchmaker Make Me A Match

My mother's best friend had a son who just got released from correctional facility. We were told he ended up there because he took the fall for someone carrying a ton of illicit substances. He was doing tattoos for a living. At the time, in our state, tattoos weren't allowed, so he and his mom came to our house to give us a tattoo. I was about 18 years old and, I believe, he was in his early 20s.

His mom kept hinting (and eventually outright suggesting) that I let him take me out on a date. She was adamant that he needed a good influence in his life. Someone like me. I'll admit, I did feel pressured quite a bit. His mom was one of my favorite people in the world and I didn’t want to let her down. But I was not feeling it.

The dude was not attractive at all. Worst of all, he was covered in disturbing tattooed symbols. He claimed it was to survive while behind bars. I also found it really creepy that he kept oddly stroking my foot while doing a tattoo several inches above my ankle. I was relieved that we managed to end the little tattoo party with no dates made. Cool.

About three months later, I'm listening to the news as background noise. Suddenly, I hear this guy’s name mentioned. The authorities are frantically looking for him and giving his description. Turns out he ended his girlfriend and all four of her children after the girlfriend caught him touching one of the kids.

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14. Stuck In The Friend Zone

I was incredibly close to a gorgeous girl in my friend group. We’d dance at raves together, party, and make out. Most nights, we’d talk on the phone for hours and hours. But, whenever I’d ask her out on an official date she’d always say the same exact thing. “I don’t think I’m ready for a boyfriend yet but I like what we have”.

Well, soon enough, she meets an ex-con and begins to date him. They both start doing some pretty hard substances together. Like, scary hard stuff. She runs up a few thousand dollars on her dad’s credit card and, big surprise, ends up getting kicked out of her house. So, she moves in with the ex-con who is now her boyfriend, and some other friend.

Then, one day, her crazy boyfriend absolutely trashes the place in a wild, inebriated rage. Of course, they all end up getting kicked to the streets. Some years later, I’m curious about what happened to her and poke around for an update. I find out she’s been taken in by authorities a few dozen times and is serving a three-year sentence.

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15. He Was A Skater Boy

I moved to a small town in Ohio when I was 14 years old from New York City. There was this girl a year older than me who I met at a church youth group. We would make out at the bus stop before school and hang out together at church events. We went on a few dates and to dances, but were only a couple for about three months. That's when it all came crashing down.

I saw her wearing the hoodie that belonged to a skate park guy. It turns out she was only with me because her parents wanted her to be with a “nice kid” instead of with the kid she liked and she would tell them she was with me when she was actually with this dude.

Fast forward two years and she drops out of school at 17, pregnant with skate park boy's baby. Fast forward another few years and she's making money selling substances and struggling with addiction. Skate park boy is out of the picture. He’s been replaced by a string of men who take advantage of her. Fast forward a few more years and I run into her when I visit Ohio at a coffee shop.

She sits down and tells me her story. She tells me I was her first true love and the only guy who treated her right. She asks if I'm moving back and if I want to get back together. I tell her I'm married. She cries and I buy her a cup of coffee and listen some more. I give her the number of a counselor and therapist.

A long time goes by and I don’t think of her. I just found her on Facebook now and she's six months sober and getting her life together.

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16. Woman Seeks Mature Man

When I was 18, I dated this girl for a few months and thought she was the love of my life. The whole time we were together, I thought she was about a year older than me so it came as a huge surprise when she ended up dumping me for “being too young”. She claimed she was “too mature” for me. Okay, fair enough, but kind of harsh.

Now I’m turning 30 and just found out that this girl has been divorced twice already and has three kids. She’s been in court fighting over child custody at least once that I know of. Her mental health isn’t good and she’s in emergency therapy.

I’d never wish this hardship on her, but I’m glad I wasn’t the one she deemed “mature” enough to have kids with so young as I probably would have. Phew.

Man taking photo of a coupleLouis-Charles Blais, Pexels

17. Spider Senses

I dated a guy for a few months and I really liked him, but something just started to feel off. It’s hard to explain because he was never aggressive or weird. Still, I sensed there was something about him that didn't feel quite right. I ended up breaking up with him over text. I know, it’s horrible. But I was a teenager and didn't want to break up face-to-face.

Even though I never heard from him or saw him ever again, it didn’t really stop there. He was angry about the breakup and talking about me to others. My best friend, the one who had introduced us, told me that he was saying disturbing things about me. It was dark stuff like how he hoped I would hurt myself and take my life.

Eventually, he forgot about me and moved on. He started dating a new girl. But when she told him she wanted to break up, he apparently freaked out and stuck a blade in her. He then injured her in other ways and went on the run from the authorities. When they found him in a neighboring country and tried to arrest him, he became aggressive!

So, yeah. Even though I really liked him I'm glad my spidey sense was tingling!

Angry man in black hoodieCraig Adderley, Pexels

18. A Lost Soul

My high school girlfriend was a lot of "firsts" for me. She also cheated on me multiple times and introduced me to a lot of substances that I definitely didn't need, etc. Anyway, sometime after getting myself involved with the authorities and expelled, I finally woke up and realized that I was just being used for different things.

It was still super difficult though. I think first experiences tend to have that effect. So my girlfriend went ahead and promptly had a kid with some lowlife in town and then, a couple of years later, went and had a second kid with another lowlife. I went quite a while without speaking to her until one day, out of the blue, I received this random message from her. 

I thought, “Oh wow. It might be nice to catch up and mend some of the past," since I still cared about her as a person. Then she immediately asked me for money. Hahaha, guess you're still the same person! She passed about a year ago. Her mom, who is in her 60s, is now taking care of two young children by herself in a state pretty far away.

My heart breaks for all of them. Wish she could have realized that there were people who loved her. Wish she was still here to take care of her boys. Wish a lot of things.

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19. That Outfit Is Familiar

I started seeing this woman earlier this summer that I met through an online dating site. Around the fourth date or so, I discovered that she is an awful mother with two kids from two different men. She also has not paid one nickel in child support. Things started to get suspicious for me when she never had her ID on her.

So I did a cursory background check on her. It revealed that her license is suspended in three states because of unpaid child support. Just a few hours before our date, she got taken in on a warrant for the unpaid child support. She was even wearing the same clothes in her booking photo that she wore on the second date. She was hot but yeah…thank god I dodged that.

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20. A Real Winner

Me and this guy were really vibing at first and we were talking every day. I thought for sure it was going to turn into something. Well, it turns out that while he was casually talking to me, he was also talking to another girl. One weekend, I go away on a trip with my family and he spends some one-on-one time with this other girl.

Well, she becomes pregnant with twins and he has to drop out of high school in order to support them. Shortly after the twins are born, he develops a substance problem and ends up leaving them. It doesn’t take long for it to spiral into a major, full-blown problem that lands him behind bars for a year.

He's out now, works odd jobs for cash, and evades child support. I heard he got another girl pregnant whom he also left. Wow, am I ever glad we didn't become a thing.

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21. Don’t Mess This Up

I was dating this guy for a few weeks. There were some major red flags but what convinced me to cut him out of my life happened after our last date. He pushed me up against my car and said, "Don't mess this up". I completely avoided him after that. Luckily he didn't know where I lived at that point because I'd go to see him.

A month or two later, I saw him at a Christmas party and he had a new girlfriend. I was a bit worried for her so I managed to get her aside when he wasn’t looking and told her to be careful.

This guy had serious crazy eyes. Maybe a year later, I’m watching TV and guess who's mugshot comes across the news? Yeah, you guessed it. It was him. Turns out, he absolutely lost it.

His girlfriend dumped him, so he showed up at her house in the middle of the night, plastered and angry. He busted into the house and dragged her out onto the front lawn by her hair. The neighbors called the authorities. When they arrived, he fired at both of the officers! One in the neck, one in the leg.

Somehow, one officer was the one able to get him in cuffs. I couldn't believe it.

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22. Miracles Are Real

There was a girl that was great across the board. She actually approached me and asked me for my number. That was the first time any girl ever did that to me so I was really excited. We talked for a while and had a ton of stuff in common. Same music, movies, games, etc. She was very much my type. Beautiful girl. Half of my friends didn't even believe me that she was talking to me.

Eventually, we started dating and everything was great for a couple months. Then the other shoe drops. She tells me that her family has always had issues having children and she is not able to get pregnant. I asked her, “How do you know that”? and she tells me that she’s never had a period before. She has even gone to hospitals and had tests done. She says she is completely infertile.

So, she says, there’s no reason to even use birth control. It doesn't matter. The look on her face and the look in her eyes kinda weirded me out. Like, I could just tell something wasn't right. I said, “No it's okay. I'm fine with using birth control anyways because of STDs and just to be extra safe”. But she INSISTED on no birth control. Just begging me to do it.

But I gave a firm “no” and it just didn't sit right with me. I tell her I'm sorry but we have to break up cause something just feels off. We almost got back together a few times because I started to miss her and thought I might have been overreacting a little. But some of my female friends agreed with me and said it didn't sit right with them either. So, I ended up walking away.

Well, not even three months later she is with a new guy and it’s a miracle, she is pregnant! It turns out that she was an absolute psychopath. She magically turned into a huge farm girl and basically became a carbon copy of her new boyfriend. I have absolutely no idea where she is now because she really gave me the chills. Yikes.

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23. State Hopping

I dated a guy in high school for about six months. He broke up with me for another girl. It turns out that they didn't last long and I ended up moving to the state next door. He would come to visit me but I decided I didn’t want a long-distance relationship. I was only 15 years old (he was around 18 or 19). So I cut it off.

So, a few years later, I got a phone call. Apparently, my ex-boyfriend had run away to another state with his new girlfriend who was 16 years old. He would have been around 24 or 25 at that time. I was shocked to find out that he had taken her life and then his own when they got to their destination.

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24. Ugly On The Inside

I dated a guy in 2012 who I thought was super hot, smart, and successful. He dumped me after nine months because I wasn’t “hot enough”. Cut to this year and I saw his face with the collection of mugshots as part of the white supremacy group who were taken in by authorities before invading a Pride celebration in Idaho. It made national news. But here's the plot twist.

We are both gay men. To clarify, it’s hard to tell who he is in the mugshot because everyone looks awful in mugshots, but he was really hot in 2012. Short and muscular, very much my type. After we dated, he moved from Colorado to Wyoming and ran for public office but ended up losing. He never had a chance, really.

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25. What Nightmares Are Made Of

I dated this girl for a few months online. Suddenly she vanishes and deletes all her social media. Some dude pops up looking for her, saying he was her boyfriend. I said, “Yeah, me too” and he calls me a liar. I block him. Six months later, she returns and says he was a crazy stalker.  My gut said she was lying but it sounded plausible since he hunted down her friends and family. I should have listened to my gut.

She goes missing again and her mom left a bunch of people nasty messages about us "taking advantage of her daughter". We were all confused. I began digging around to figure out what was going on. It turned out she was deemed incompetent by a psychiatrist. I found a couple of old groups she was in—and discovered something scandalous.

She was having a relationship with six other guys. She had four boyfriends, one “daddy," and a "master". She told each guy they were her love, then told stories about all the other boys being stalkers. It turns out I was one of the guys. The “stalker” was too. When she returned once more, me and many of the other guys dropped her all at once.

She sent me pictures of her slashing her arms with a blade. The caption said, "When they find me gone, my last messages are to you so you go to correctional facility for life". I called one of her family members and they busted through her door and took her to a psych hospital.

Later, I learned she had a local boyfriend and when things went south, she faked an allegation as revenge. The courts didn’t believe it and he went after her for defamation of character. The reason she kept vanishing online is because she kept going after him and his social circles by using fake accounts.

I actually ended up being put into a psych ward over the situation. Nobody should see a person they loved attempt to harm themselves just to hurt them. After I got out, I got a crazy message from her family. They asked me how I was doing and hoped I'd try again with the girl in the future. They said I was a good guy and she needed that.

They then asked that I keep her revenge harm attempt and fake allegations to myself because they "didn’t want it to make her lose all her internet friends". I blocked them and changed all my account names and pictures. I took screenshots and told everyone I possibly knew that had any kind of connection to her.

To this day, I still have panic attacks when random people message me because I immediately think it’s her and that she’s going to try and take revenge against me again. At least I didn’t marry her. But I have never completely recovered from that nightmare.

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26. Scary Fan Girl

Talked to an attractive girl over text but it never went anywhere. A couple of years later, I see on the news that she was taken in for conspiring to plant explosives at her workplace. The FBI found "fan art" of her favorite serial slayer at home and discovered that she’d been sending mail to him in correctional facility.

Twisted Dating StoriesFlickr, Michael Pollak

27. Seeing Red

Before I met my serious boyfriend, I was talking to this guy in the Navy on an online dating platform. It was purely casual talking with maybe some slight feelings. We FaceTimed a lot and stuff, but it was meant to be just talking, nothing more. One night, I went out to Taco Bell with my best friend, who happens to be a guy.

I happened to be wearing red lipstick. This. Guy. Flips. I get a barrage of messages like, “Who are you with? Why are you with him? You shouldn’t be wearing red lipstick. Do you know what happens when women wear red lipstick? If you’re going to play games, lose my number”. The only response I had was “it was never saved” before blocking him.

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28. Red Flags At Night

I really liked this guy. I was a terrible flirt, but we eventually did date. I ignored some red flags that pointed at some mental illness and anger problems, but these became much more apparent after we started dating. He really needed some therapy or some form of help for his depression. In hindsight, his anger was really scary.

He was obsessed with an ex-girlfriend and did a lot of online stalking. He complained about her and wished her harm. We dated for two weeks before he dumped me for a chance to get back with his ex. That didn't last long and he came running back, but I refused to get back together.

He would beg, demand, and bug me nonstop any time we would run into each other or talk over text/social media. I got sick of it and blocked him. After a few years, I stupidly unblocked him, thinking he wouldn't bother me anymore. He eventually realized he could message me again and was very quick to pick up where he left off.

I blocked him again, this time for good. I'm sure he talks about me the same way he talked about his other ex, despite it being years since we last spoke. But I truly hope he got some help.

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29. Sign Up For The Latest Updates

My first love was "perfect" to me in every way. Her family loved me, too. Both of our families got along really well. But, because of the hour-long drive to see her, I was completely unaware of her other life. One thing I knew she lied about was being a virgin. However, after getting dumped by her, I found out a lot more.

I never suspected her of cheating on me. Apparently, I was the “other” guy while she was actually with her supposed “ex” boyfriend the whole time. She was using substances with her stoner best friend all the time and she ultimately dropped out of college. Her family kept all these secrets in hopes I could save her from herself. Her mom even accused me of not trying harder after getting dumped.

After spending News Years' Eve 1999 all alone and failing college myself because I couldn't cope, I met my future wife and turned it all around. On Valentine's Day 2000, my ex surprised me at my workplace. She's officially single, very sorry, and wants to try again. I want to say that even if I was single, I would say no, but thankfully, I was NOT single.

I decided that I will stay with my current girlfriend because she is worth it in every way. After a few tears, my ex left. Unfortunately, now, because my ex and both of our families remained friends all this time (despite the utter betrayal), I get to hear constant updates on my ex's situation. FOR 20 YEARS AND COUNTING.

For instance, I know that after a series of abusive drug addict ex-boyfriends, she got a good-paying management job, before relapsing and losing it all. Then, I heard that she decided to become a drug counselor and enlist in college. She dated another guy in the same program, a fellow addict. Well, the two of them relapsed and dropped out of school.

He took what he could and left her. She ended up on the streets before her mom found her panhandling. And I get to hear about how her greatest regret was dumping me, over and over again. So yeah, bad situation avoided. I try not to show concern for the ex's situation for the sake of my wife and kids.

But, honestly, it still hurts me deep down that she is suffering, that my first love was an illusion, and at her lowest, she's still crying out for me. I hope that she finds peace and happiness someday, someone to love who doesn't remind her of me. She's paid for what's been done many times over.

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30. What Could Have Been

Recently, I reconnected with my first girlfriend after 17 years. For one thing, time has not been particularly kind to her. But that wasn't the worst part. She ended up becoming a two-faced, manipulative, gas-lighting, cheater.

She was cheating on her fiancé, who also happens to be the father of her child. This affair went on for six months before she finally broke it off with her fiancé.

So, the relationship with the other guy continued for another six months before he kicked her sorry self to the curb. That was about a year ago. Even then, it took her months to tell the baby daddy. I’m not sure which side of the aisle I stand on as far as telling him after the fact. But it still feels pretty shady to me.

Now she’s pretty much just wallowing around in self-pity, acting like she’s better off alone forever. After some of the two-faced stuff I’ve seen her do, I’d say that’s probably accurate. I do feel bad for her ex-fiancé because he’s still hopelessly in love with her. It’s sad because he doesn’t seem to be handling things very well.

And I can totally understand where he’s coming from. I can say from experience that this woman is extremely convincing to your face, but you have no idea what she’s saying or doing behind your back. I feel like if he knew or understood what she actually did to him, it would help him move on. But that’s obviously not my business to butt into.

Anyway, this is only just the tip of the iceberg. There’s a lot more to tell but I’m not going to get into more of the gory details. Essentially, I had spent a lot of time wondering what might have happened if circumstances had allowed me and her to properly continue our relationship. Now I know, and I’m glad they didn’t.

Twisted Dating StoriesUnsplash, Valentin Salja

31. Not On The Same Page

There was a girl I was pretty in love with throughout college. When we met, she had a long-distance boyfriend, but we got super close—weekly dinners, meeting on campus multiple times a week to hang out, etc. She broke up with her boyfriend one summer and when she got back in town, she and I went to a movie and had dinner. But it didn't last long.

A couple of months later, she was dating someone else. At the time, I really, really kicked myself. When I look back on some interactions, I really think I had a shot that I was just too scared to take. I just kept thinking that if I made a move, I could ruin this friendship that meant so much to me.

I wasn’t really thinking about the fact that post-graduation, we would only see each other once or twice before she moved across the country with the guy who became her husband.

Well, now I'm gay and REALLY glad I never tried to get into a serious relationship with her…or any woman. I was gay then, too, of course, but still deep in the closet. Now it seems like she has a great life and is still an awesome person, but I probably would have made us both miserable if we had ever tried to make it work.

Twisted Dating StoriesPexels

32. Teen Romance Movie

My “story of narrowly escaping a problematic relationship” was my high school boyfriend. We had this really intense crush on each other for the last three years of high school, but never knew we liked each other until senior year. At the end of senior year, we finally got together, and it honestly felt like the happy ending of a teen romance movie.

Except after dating for a few months, he broke up with me because, according to him, we were of different religions and he wasn’t sure I could commit to the virtuous tenets of his faith. I also suspect it was because once he got to know me as his girlfriend I suddenly wasn’t as exciting as when he was pining for me from across the room.

Long story short, I was devastated for a full year. He dates around a bunch and then goes on a religious mission trip. I’ve been with my husband for a full ten years now, we have two great kids. My ex? Married the girl who waited for him while he was on his mission. They divorced a year and a half later. He’s on his second marriage now.

I don’t really think about him that much anymore. Every once in a while, I remember the stupid fights we would have and how he made me feel crazy for expressing how I felt and how often he made me cry. And then I think about my fertility struggles and other tragedies that happened in my family over the past ten years.

I am so thankful I went through it all with a wonderful man like my husband at my side, instead of my high school ex. Moral of the story, your high school romance probably won’t be your forever relationship and thank goodness for that.

Twisted Dating StoriesPexels

33. Don’t Leave Me

I dated a guy for two years. I was madly in love with him, but the issue was he would not take care of his own mental health and often dumped all his problems on me. And when he wasn’t dumping his problems on me, he took out all of his anger on me. Finally, I decided I had enough of this treatment and knew it was time to break up.

When I went to break up with him, his reaction shocked me. He started crying and begging me to stay, saying that he’ll work on it. Of course, this wasn’t the first time he’d promised to work on it. I felt guilty for the longest time for giving up on him even though it was the best choice for me. I found out months later that he was cheating on me for months during our relationship.

Twisted Dating StoriesPexels

34. That Went Downhill

I met her when we were in high school. Her name was Jesse and she was the first girl who paid attention to me. I was head-over-heels in love with her, just absolutely swooning. We "dated" (as much as you can say that, as two 14-year-old kids, holding hands in the hallway between classes, long conversations on the phone after school, going to the movies and cuddling, that kinda thing). She was also my first kiss. It was as much "your first love" as you could possibly get.

I was barely a teenager, and I was convinced she was going to be my wife someday. If you've ever been 14, you know how it goes. After freshman year of high school, she moved about 30 minutes away to another school district. But, to a kid who couldn't legally drive for another two years, she may as well have been on the moon. Of course, I was devastated.

We remained friends, but I always wanted more. Jesse kinda kept me around because she liked the attention. She always "teased" at getting back together, but it never amounted to anything. It wasn't until I was older that I realized how manipulative and cruel she was. She went on to date a whole slew of characters all throughout high school, eventually landing on her second cousin at 17.

They dated for a while and even though her family was pretty accepting, everybody seemed to acknowledge that it was really pretty weird. Sometime after that, she broke up with him for some guy she just met. They high-tailed it to Alaska after graduation. From there, they took skiing lessons, and she falls in love with the ski instructor.

The dude she drove to Alaska with gets dumped and the poor guy had to drive all the way home to the midwest. She winds up having a kid with the ski dude. That was years ago now. We've since fallen out of touch as I've moved on with my life. Last I heard she dumped the ski instructor and went on to her next guy.

So, as a 14-year-old-just-figuring-things-out, you could call her "the one that got away" but, man, am I glad she dumped me.

Twisted Dating StoriesPexels

35. It’s Not You, It’s Me

I was in love with a girl, but was too scared to do anything about it. Eventually, she got tired of waiting and moved on to a sociopath who I used to think was a friend. He used me to get to her and then he told me that "if I want to sleep with her, I just have to wait until he gets bored with her, there's nothing easier than taking advantage of a girl who needs a shoulder to cry on".

After that, I was a mess and I acted irrationally. I finally declared my love, then I would send her 50 messages a day demanding an answer or telling her to choose between me and him. I was convinced that she was my only path to a relationship and happiness. I became increasingly paranoid.

I figured that if one person I thought was a friend could betray me and say something like that, then anyone can. So, I isolated myself. In addition, I hated myself for my breakdown. I hated how I was acting, hated harassing her, and more. I was not in a good place, so I took off. I moved to another country.

Moving helped. But, when I started socializing again and met new girls, I found that I would get very controlling and annoying. For instance, when I'd meet a girl I got along with at a party, I would follow her around, inject myself into every conversation she was having, etc. I knew I didn't want my insecurities and issues to affect other people.

So when the pandemic came along, I was kinda happy for the opportunity to deal with my problems without any social pressure. So that's what I've done in the last few years. I feel like I'm in a pretty good place now and I'm ready to get back out there. As for the girl, she ended up in a very controlling relationship with the sociopath.

When she first told me, I was furious. I told her to come live with me, that I would treat her right. Which was a lie, of course. I would have been just as controlling, if not worse. She called me two weeks ago and told me she dumped him. We're slowly getting to know each other again, but I know I don't want anything romantic with her.

She was one of my best friends before things went bad, so I want her to feel free and happy. I'll offer to help, but we're both different people than who we were before things went bad. Anyway, she was the one that got away. But she wasn't the problem, I was. Too bad she dodged right into the path of another one.

Twisted Dating StoriesUnsplash, Jeremy Perkins

36. Downward Spiral

I have a story about my girlfriend's ex-boyfriend. She didn't know half of what he was doing until she was going through the divorce. People started fessing up to her about things they knew he was keeping from her. If you can believe it, he slept with someone on their wedding night. In fact, he cheated constantly on her.

Once, he started his own business and would only hire girls who he intended to cheat with. He had a narcotics habit for most of their marriage. Somehow, he managed to hide it, but it got worse.

It got so bad that he spent all of the money from his business on those substances until it all had to shut down. She's absolutely great and I'm doing my best to be empathetic since I've never been in any situation like that. I can understand why people develop trust issues.

Twisted Dating StoriesPexels

37. Run Away Screaming

Years ago, I met this guy that I instantly became friends with due to a mutual interest we had. We started talking and started becoming pretty close to the point where I started to develop feelings for him. He ended up rejecting me, but we still remained friends.

One or two years went by and we were still talking. We never dated, but he always treated me like we were and called me a bunch of nicknames. In hindsight, there were a couple of warning signs that this dude had some problems, or at least was developing some problems.

Maybe I was naïve or blinded by love, but I never picked up on the fact that this guy was a huge creep. Like, toward the end of our friendship, this dude was ranting about how the age of consent should be lowered so that he could get with kids. This man, in my opinion, is an absolutely pathetic excuse of a human being.

He essentially made liking young girls his whole personality. It’s sick and horrifying. So, what else could I do but report him to the authorities? I only had a bit of evidence but someone on the internet gave me advice on how to go about reporting him. He lives in the UK and I live in the States.

Sometime in the future, I want to report him again just to make sure he is rotting away in correctional facility and away from children.

Twisted Dating StoriesUnsplash, Ihor Saveliev

38. What If

There was a gorgeous girl in my large circle of friends during undergrad who really stood out to me. She was slightly alternative amongst a sea of carbon copy sorority girls; loves music, is extremely fun and adventurous, graceful, kind, and has a beautiful singing voice. She just caught my attention. I felt like I really “saw” her.

For the entire four years we lived in that town, we would intermittently be together in social situations, parties, and ski trips. There was always this tension that bordered on being more than just flirty. Her close friends undoubtedly picked up on this. There was a murmur from them that she was “different” in a way that I wouldn’t understand and that we couldn’t be together because of it. That didn’t really make sense to me, so I ignored it. We continued to be in each other’s orbit off and on.

One day, in my senior year, I got the courage to step up and take her on a fancy date. The tension was so thick. We were sitting at a bar after dinner, staring into each other’s eyes, and just left our drinks right there on the counter and went home to make love. We had this wild up-and-down interaction for the rest of that year.

We had an incredible level of intimacy, although it was sporadic and fleeting. I would see her, then I wouldn’t. We never discussed being exclusive, but I secretly wished she would be a consistent part of my life. I felt a lot of things for her, but I never shared any of it with her. I dated other people, graduated, and moved to the big city. She came and stayed one time with me and it was magical. But she became distant again.

A year or two later, a friend of mine ran into her back in the college town. He told her that I always talked about her and obviously missed her. Then, she called me out of the blue, surprised I was still thinking of her. We got together again. We had both recently moved and it turned out we were living in the same new city.

The passion and intimacy was explosive again. I imagined starting a life with her, but it just never stuck. I just couldn’t seem to get the commitment vibe from her. Life went on. I met someone whom I fell in love with, and moved away again. More than ten years have now passed. I got married, have kids, and a very full life now.

As one does, over the years, I’d occasionally think back on our time together and wonder “what if”. One day, out of the blue, she contacted me on social media and told me that she’s seen my life unfold and is very happy for me. It turns out that she’s married as well. To a woman. A lot makes sense now and I’m very happy for her too.

Two girls looking at yellow wallRogério Martins, Pexels

39. Ghost Girl

We matched up on the Tinder app during our freshman year of college. It was awesome. We met up for a lovely little coffee date and then met up again shortly after to study together. We kissed. But after she went home, she ghosted me. It was so weird because I felt like everything was going fine but she just disappeared.

She had “read receipts'' turned on and I would occasionally check to see if she actually read my text message, but she never opened it. Suddenly, during our second semester, she answered my text message as if only a short time had just gone by. I thought it was so strange but, whatever. I guess it was nice to talk to her again.

We kept talking until I broke the news to her that I had decided to transfer to another school. After that, I rarely heard from her anymore. And it wasn’t like I was so far away. The distance between her school and mine might have only been about an hour’s drive, so dating after I transferred wasn’t completely impossible.

So, now it’s our second semester of sophomore year. We started talking again. I don’t remember what sparked it. She came to my school a few times and we would hang out, study, and goof around. It was lovely and I thought things were really good between us for about two weeks. And then, guess what? She ghosted me again. I’m laughing now thinking back on it.

Two years later and it’s our senior year of college. Somehow we got to talking again and we went out on a few dates. Things actually stuck this time. We graduated and moved in together. This is where I feel like I should have recognized a bunch of obvious red flags that I ignored because I was so infatuated with this girl.

She was extremely selfish and showed signs of being a narcissist. I had ignored all of these signs because she disguised them really well as being a quirky person. She was extremely manipulative and a compulsive liar and worked me just like she would work other people. Eventually, she started cheating on me, gaslit me, and then fell into a horrible depression.

Finally, I couldn’t take it anymore. Why was I trying to keep a relationship together with someone who didn’t care about me? So I broke up with her. I wish I'd gotten out earlier, but I learned a lot of valuable lessons from this relationship. Pulling myself out of that deep hole helped me to be a much healthier and happier person. Cheers to healing!

Twisted Dating StoriesUnsplash, Lance Reis

40. Must Love Dogs

Was always curious about what became of my high school “girlfriend," aka that girl that tolerated my presence in high school and made out with me a couple of times, so I stalked her a bit on Facebook. Turns out she’s happily married to some lady and lives in a house in the country with, like, a billion dogs. So, clearly, this would not have worked out, as I’m allergic to dogs.

Twisted Dating StoriesUnsplash, nrd

41. Life Is A Stage

In college, I had a class with a guy that I thought was really cute. We ended up working together on a short assignment early on and I can't say what it was exactly, but I remember losing all attraction for him pretty abruptly. He stopped attending classes midway through the semester. Then, a detective showed up in our class and made a horrifying announcement. 

He said that the cute guy had taken the life of a student that he had been dating. I'm not saying it was some "I knew there was something wrong with him" type thing. Honestly, I think it was more that I thought he was arrogant rather than potentially dangerous. But I am forever glad that whatever intuition I had about him shut that down.

Apparently, he had been dating and scamming a bunch of girls at the school. He claimed to have cancer and borrowed money from them. If I had shown any interest in him, he probably would have done that to me too. Anyway, the reason the detective spoke to our class was because this guy had written a disturbing one-act play.

He wrote a play about a guy who's being interrogated by officers regarding his deceased girlfriend. With the timing of it all, he would have written the play right around the same time the real-life incident took place. The authorities were trying to figure out which came first. If the play came first, it could be used as proof of premeditation.

I think it’s clearly obvious that he did it but the officers were trying to prove it.

Twisted Dating StoriesPexels

42. Take Out

I used to work with a girl at a restaurant. Well, I had a crush on her. We made out one time in a field. I figured we would stay in touch, keeping in contact on-and-off. I kinda never really heard from her in a while. I wondered what happened.

She ended up getting taken in for hurting her children and taking the life of a former co-worker's kid. I think about this a lot because she had met my child at the time.


Twisted Dating StoriesUnsplash, Priscilla Du Preez

43. Good Cop, Bad Cop

I dated an officer for about six months. He wasn’t cringey and we had insane chemistry. We really connected. In my mind, I was already dreaming about our wedding and planning all the details. It took a little time, but I discovered that my cop boyfriend was not as monogamous as he pretended to be. I was absolutely gutted. What else could I do but end things immediately?

Fast forward 12 years and I find out some interesting information about him. He was indicted and convicted for several serious offences. Clearly, I knew nothing about the guy. I shake my head in disbelief whenever I think about the irony of my heartbreak and how things could have turned out.

Twisted Dating StoriesUnsplash, Jacky Lam

44. From Hot To Cold In 30 Seconds

This girl I knew had a boyfriend who was always a jerk to everybody. All our mutual friends agreed that she should break up with him. After some time, she finally realized that he was a bad dude and told us she was close to ending things with him. Then she got really flirty and forward with me and I was into it, and she even told me she wanted to kiss me.

I told her to dump the other dude first and then we could give things a try. I liked her too so I would look forward to it. When she did dump him, I went ahead and asked her out on a date. Suddenly, out of nowhere, I was a creep and a bad guy and if I thought she had any interest in me, I was wrong. Like, where did that come from?

Twisted Dating StoriesUnsplash, Maria Lysenko

45. Ya Think?

I once dated a guy who was a extreme Satanist. I left him because I was getting bad vibes from him. When he got back with his ex who was the so-called “love of his life," he cheated on her twice and began having constant one-night stands and just cheating on every girl he was with. He got another girl pregnant. Man is for real a hustler.

Twisted Dating StoriesUnsplash, Sander Sammy

46. A Very Close Call

This crazy story didn’t happen to me, but to my high school girlfriend's mom. I was floored by this. The story goes that when she was in college, she was out at a bar and met a cute guy. He was charming and suave. He even wore a sports coat to this dumpy little campus bar! He said he was a law student. Pretty impressive so far.

So, she almost gives him her phone number. Almost. Something stopped her. You see, at this same time, there was some scary stuff happening in the area. A bad man was on the loose. He was wreaking havoc a few streets over at a sorority house. Women in town were on edge. So, even though she liked this guy, she was playing it extra safe.

A week later, she sees the guy in the newspaper and gets a call from the Tallahassee authorities. Apparently, they had found her ID, among others (many of whom were deceased), in his personal effects. Turns out she was his "type": slender, blond, age 17-30. He was probably stalking her at the bar and had nicked her ID for her address. That suave law student was Ted Bundy.

Twisted Dating StoriesPexels

47. Sick Puppy

I met this one guy as a young adult. He was a mutual in my friend group. I thought he was cute. I gave him my social media info and we chatted back and forth for a little bit. Not long after we met, I ended up moving away from the area. After I moved, he messaged me constantly, asking me to come over to his house, attend parties with him, come to his area so he could buy me a drink, and so on and so forth.

I politely declined him every time. This went on for literally an entire year. Eventually, I entered into a committed relationship with a great new guy. Shortly after, this stalker asked me if I had a boyfriend. I said “yes”, and he proceeded to send me a bunch of gross, intimate pictures of himself. I instantly blocked him.

Two years later, through our mutual friends, I found out that he had been accused of some extremely disturbing acts involving several women. He would give them pills and hurt them. When the authorities came to his house to take him in, they made a disturbing discovery.

They found a woman in a dog kennel in his living room. Not sure the entire story behind it, but just thinking about it totally freaks me out.

Twisted Dating StoriesPexels

48. Family Resemblance

When I was in high school, people would approach me because they thought I was someone named Tina. It happened quite a few times. Then I started to date this guy. It turns out Tina was his sister. Even he mentioned how much I looked like Tina. And he pointed out how that meant we looked like brother and sister. My friends made fun of me all the time about it.

In fact, a friend pulled me aside and told me that everyone was making fun of us behind our backs because of how much Tina and I looked alike. Once, he even asked me to wear her hair in a side ponytail, which was her signature style. He posted a picture of Tina in a towel on Facebook with the caption “Tina looking all hot and wet”.

Twisted Dating StoriesPexels

49. Wanted Man

I was dating this guy and he had been staying over at my house a lot. One day an officer followed me from work, stopped me in a parking lot, and showed me pictures of my boyfriend. The officer demanded to know where he was. Long story short, my boyfriend had a warrant out for stalking and worse. The officer followed me to my house.

A whole bunch of officers were there and caught my boyfriend outside. It totally sucked. And the officers were jerks too, saying they were gonna arrest me for harboring a fugitive. I mean, what?? I was traumatized and angry that I got roped into all this, but thankful in the end. The whole crazy situation got me away from that awful man.

Turns out my so-called “boyfriend” was a manipulative, abusive liar who bums off of girls. That’s his pattern of behavior. Only six months later I found out something very disturbing. He landed himself behind bars again, this time for strangling his next girlfriend. I am very thankful that was not me.

Twisted Dating StoriesPexels


Sources: Reddit,


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