“Don’t come back when you realize that I’m rare.”— Genereux Philip.
Breaking up is tough to do. Staying broken up is tougher, at least according to several Redditors who shared their worst tales about the ex-partners who just wouldn’t let it go. Everyone deserves to exit a relationship safely on their own terms, but some people missed that memo. From unwelcome desserts to elaborate medical stunts that went horribly wrong, we have to wonder why these exes didn’t put all this creativity into being better at relationships. Alas, some couples just aren’t meant to be—and thank goodness for that. Read on for these 42 chilling stories about the worst exes.
1. She Stole My Heart
Here is one of my most recent experiences. I dated a woman for around two months and finally realized that things were just not going to work out. We sat calmly at my table and broke up, amicably, I thought.
I went to put the kids to bed and tell them a bedtime story. I ended up falling asleep while telling the story. When I woke up, my laptop was gone, my extremely nice winter coat, my cast iron pots and pans, pictures I had taken while overseas. I was shocked and hurt. Thankfully I still had a cheap pan left and decided to make myself a late steak dinner. Oh. Whoops. She took my steaks.
2. Fake-Out, Make-Out
Best I got is when she pranked me into believing she cheated on me with a friend of hers she knew I had concerns about (he openly admitted to me that he loved her). Then when she came clean that it was a joke a couple minutes later, got extremely upset with me over falling for it.
3. Big Girlfriend Is Watching You
GF snuck into my apartment while I was sleeping. Sat at the edge of my bed for three hours and watched me just to make sure I wasn't disturbed...
4. Do You Keep It in the Family?
An ex-boyfriend of mine was so jealous that he accused me of having an intimate relationship with my brother.
5. Bullets Dodged
After we broke up, he threatened to blackmail me with an intimate tape he'd taken of us (without my knowledge or consent) if I revealed to anyone that he was a dealer. Great guy.
6. Bull in a China Shop
Summarizing: he was the kind that never apologized and bought people with expensive gifts every time he'd mess up. When he did that to me, I broke up with him and refused to take his gifts. He was very confused and kept asking why I wouldn't go back to him, since he bought me so much good stuff—and didn't understand even after I lectured him, becoming increasingly angry with my (friendly!) refusals.
Then he threw the things against the wall and rammed his head through the window. Broken glass and blood everywhere. I called an ambulance and his family, and after that I noped out of the relationship for good.
Nowadays he's married, but our mutual friends say he's still in love with me (and doesn't hide it from the wife)... he asks them questions and tries to set up "accidental" encounters. I asked them not to share information about me with him anymore.
7. Road Trip of Regret
My ex-wife cheated on me, lit my house on fire, took my daughter to Puerto Rico without telling me, abandoned her daughter, ran away to Barcelona and shacked up with a guy, came back and expected me to forgive her... That's only the tip of the iceberg.
8. Sweet Estrangement
She bought me a 20-square-foot cinnamon pretzel for my birthday. Good crazy.
9. A Saga in a Sentence
Had a girlfriend not tell me until we were dating for 2 weeks that she had a massive drug addiction.
10. Unreal Real Estate
My ex-girlfriend, who was 25, never invited me into her place. We would always hang out at my place and I would drop her off at her place. She didn't have a car either. I hung out with her and her roommate Ashely a couple of times at the bar. I never asked her why she didn't invite me in, but I did think about it sometimes.
After we broke up, a girl my ex-girlfriend knew told me why. She said that it wasn't my ex-girlfriend’s apartment, it was Ashely's apartment and my ex-girlfriend just slept on the couch like a mooch.
11. How Dare You Know?
He was super mad at me for knowing that he cheated on me with several women, because it sucks when people know bad things about you. He genuinely felt like he was the one who needed consoling.
12. She’s a Sharp One
Drove from San Diego to Chicago in two days after my fiancé went after me with a chef’s knife because I caught her in a lie (yes, she cheated) and told her I was leaving. She called her friends and family over, saying that I hit her, citing MY blood as evidence. Said friends and family threaten me and my family in the coming days before the threat of judicial action brought it to an end.
After a few days, fiancé begs me to come back, claiming that she had stopped drinking and was taking anger management classes. In the months after I returned home, I found out more dirty details:
- One of the guys she cheated with threatened that he would tell me about them, so she stuck him with a paring knife.
- Her "gay' friend had to go to the hospital after she slashed his neck with a broken piece of sunglasses.
- She was locked up a few months after I left, in an incident unrelated to the above, for domestic battery and vandalism.
She consistently emails me saying that she wants us to move forward, that we need to talk about what happened, and that we were both to blame for her cutting me. I've blocked her on my phone and Facebook, where she used to send me explicit messages and beg me to come back.
13.Frozen in Fear
My friend lived and went to school in Paris. We were out to dinner with a mutual friend, and both began talking about this guy they went to school with and both had dated. This guy had been dating this girl for a few months, but they broke it off because she got this really weird vibe their last few arguments.
My friend agreed. They both proceeded to tell stories, but this girl's were way more messed up. The guy stalked her for weeks afterwards, showing up near her apartment "coincidentally" and tipping her off that he was hot on her trail, asking her how certain events were, etc. One day she came to her apartment to find her knives had all gone missing. She remembered she had given him a set of keys. A few days later, the knives were in the freezer. She changed her locks after that, fearing for her life.
Shortly thereafter (a week or two had gone by), an old lady who lived downstairs was reported murdered. The authorities had no leads and the girl was so creeped out she moved as soon as she could.
14. Casper the Ghost
I dated a guy I worked with at a restaurant. He was a bartender and I was a server. We'd hooked up after a few months of heavy flirting. It was extremely casual (I thought) and only went on for a few weeks. Then, for reasons unknown but likely mundane (like he liked someone else, I believe) he decided to call it quits, but his method for doing this was to "ghost" me, as in to quit responding and otherwise acknowledging that I exist.
Now, that is doable when you communicate mostly by phone/email to get together, but WE WORKED TOGETHER, on the same shift! So this ghosting would result in bizarre instances where he would work service bar, I would ring up drinks for my tables, and he would stand there and act like I didn't exist, standing there right in front of him and asking him to make the drinks I rang up, which he wouldn't do because that would break the illusion that I didn't exist.
This inexplicable behavior went on for weeks. Someone must have finally asked him why he was acting so weird, because after several weeks he finally sat me down and gave me this overly wordy apology about how he hoped I wasn't too crushed and heartbroken, but he didn't see us working out. I informed him that I was never heartbroken as our time together was never very serious. He seemed let down at my lack of pining away for our lost love.
Anyway, literally a week after that conversation, I met and started dating the man who would eventually be my husband. The girl the previous guy liked dated him briefly, then ghosted him (and quit too, so it was actual ghosting, not pretend) so he tried to revive our heavy flirting routine to no avail. (Eye roll)
It wasn't the most psycho experience, but considering we were all grown adults in our late 20s at the time, it was just bizarre.
15. Gotta Go Fast
I broke up with her at her house, but she decided to follow/race me back to mine. As we were both driving, she sped past me going 20 MPH over the limit in the wrong lane trying to get to my place first. She almost got into a head-on collision with another car.
We get back to my house. I'm trying to figure out how the heck to get rid of her without hurting herself/me/my property. After she yells at me for an hour or so, cries, smacks herself, tells me not to do this, etc. she grabs a box of Nerds from the coffee table and hurls it at me. She missed me, but the box of Nerds exploded into my couch.
She stormed off...and then basically harassed and stalked me for months.
There are still Nerds in that couch.
16. Conned 0ut of Love
My ex-girlfriend who I was still relatively good friends with swiped my debit card when we were hanging out one time. She then proceeded to wipe out my bank account.
When I confronted her, she told me it was to help pay for an abortion because her current boyfriend got her pregnant. Anyways, I stopped hanging out with her and the last I heard she had joined the army and was kicked out a couple years later due to a drug addiction.
17. Director’s Cut
I gave him a Rain Man DVD after him mentioning he loved the movie, and he shanked it to pieces with scissors because he already owned it.
18. All-Natural Pettiness
Going to share a story on the behalf of my manager. He had recently broken his foot when a car jack broke on him and the car came landing down. One of my co-workers decided to buy him a plant as a "get well" gift.
His (now ex) girlfriend was convinced that that was my co-worker making a move, so she peed on the plant to kill it. Also tried to get pregnant by not taking her BC pills to trap him into a marriage.
19. It’s All About Perspective
I had an ex-boyfriend who tried convincing me and everyone else he had the upper body of a person who was 6'5" even though he was 5'11". When I was buying a new car, he told me he had to come along so he could ensure he would fit in it. I told him how ridiculous this sounded as he was only 1.5-2 inches taller than me!
20. Points for Preparation
I don't have any great stories—but I did get a "Please take me back" speech that she had written on no less than 15 index cards from which she read it. Writing on both front and back. There were footnotes and additional scribbling on the sides.
21. Pawn Stars
When I was a senior in high school, I broke up with my boyfriend. He had recently given me an (ugly) "I love you" necklace. After we broke up he asked for it back. I was out of town and said I'd give it back to him when I got home.
He started leaving rude voicemail messages on my phone, so I was like, screw you I'm not giving back the necklace. So I told him I pawned it, and backlash ensued. More crazy phone calls. He had his crazy flavor of the week call me and curse me out. Then HIS DAD started calling me and threatening me. Lots of crazy over an ugly fake gold necklace.
22. Leaving Your Mark
She carved my name into her thigh, then showed it to everyone in gym class. Luckily, I had a short name, though she did have a large canvas.
15 was an odd year for me.
23. Cooking up Something Bad
Pretty tame, but a girl I dated for a week posted a picture on Facebook of her holding a cucumber with a knife slicing through it with the caption, "I always get my revenge."
24. The Real Ex-Files
He tried to convince me that while on a camping trip with his cousin, they came across a deceased "bigfoot." While poking the bigfoot with a stick, people in decon suits from the CIA came upon them and made them leave the woods because it was top secret info, blah blah blah. He then proceeded to tell me that the CIA began following him, and they recruited him to carry out hitman-type missions for them. He wasn't a teenager when he did this. He was 25.
No, he is not schizophrenic. He is, however, a sociopath and a conspiracy theorist.
When I dumped him, he stalked me and almost got me fired from my job. He would call my department non-stop and hang up if anyone but me answered the phone. He'd drive around the parking lot and blow up my work phone and cell. He sent creepy letters to a guy I was seeing. He'd show up to a local bar I hung out at.... he lived 45 miles away and had no friends in my town.
An ex of mine once wouldn't stop tickling me and when I asked why, she said, "I'm trying to get you to punch me!"
It wasn't her kink or anything apparently? She just wanted to see how far she would have to push me before I snapped, and was really disappointed to discover I would never hit her. We broke up that night.
26. Long Distance Relationships That Never Were
Pretty late to the party but here goes. I was in Syracuse, after graduating school. She transferred to a place in Chicago. I planned to see her one weekend. Left Syracuse at 6 AM, made it to just past the Indiana border. Get a call.
Her: Hey, what's your ETA?
Me: Looks like I'll be there in two hours.
Her: omg, you're coming early? What are you going to do?
Me: I don't know. It's Chicago, I'll find something.
Her: No, you should just turn around. This isn't working.
So I did. Got home at midnight after traveling the better part of 18 hours, for 1,100 miles, through the entirety of Ohio...twice. She calls saying I shouldn't have listened to her and I should have kept going. Woof.
27. I’m Your Number 1 Fan
Dated a girl for 3 weeks. Near the end of that 3rd week she invites me back to her place and I discover she's made a shrine just for me... it looked like I had passed on, and she never got over my passing.
Trying to remember now, there was a picture within a picture frame with her photoshopped into it badly, several used napkins from our dates, and a bag of 2-week-old popcorn I didn't get to finish from our first date... so yeah.
28. On the Road Again
Years ago, had a GF I was dating for a few months, had to break it off. I go for coffee to give her the news and 4 hours later she's trying to throw herself out of my car at 80 KPH.
We went from coffee shop to parking lot where she cried more, then I started driving, pulled over again, so she could wail more. I felt like Kramer in that Seinfeld episode. It just went on and on. Then came the threats to take her own life: "I'm gonna kill myself without you" "Screw this life!" Finally, I called her friend and told her to come pick her up.
I start driving her to the pickup spot, and she's screaming and I'm driving, all of a sudden, she pulls off her seatbelt and opens the door. So now I'm driving with one hand and holding her in with the other. I had to scream to a stop in the middle of the road while she ran through a ravine.
Saw her friend, told her what happened, and her response was maybe you should let her cool off.... yeah really, Sherlock?
29. Appearances Are Everything
He was a jerk in general, very self-centered and conceited. But he was very charming, and everyone loved him, until you got to know him.
He once told me that if I ever got cancer and the chemotherapy made me lose my hair, he would dump me because "bald girls are disgusting." This was after we'd been together for almost a year.
He would also tell me what I could and couldn't wear, even if I wasn't planning to see him that day. He'd yell at me if I wore something on the "unapproved" list. It's sad that these things, along with quite a few other obvious "red flags," didn't make me realize what a jerk he was until after the relationship ended.
30. Distress Rehearsal
She faked her own overdose when I tried to break up with her. After she made hints that she would do something, she hung up the phone and wouldn't answer my calls. Fast forward 2 hours later, I kick in her door because she wouldn't answer the door either, to walk in to her laying on the couch with a picture of us and pills all over.
After shaking her and starting to call 9-1-1, she turned to me and said, "I knew you loved me." That’s when I realized she was truly crazy. Oh, young love…sigh.
31. There’s a Snake in My Boot
Was dating a guy who was pretty abusive. Had enough one day and kicked him out. His car was gone.
A few hours later, I was expecting my mother. I thought I had heard her truck pull up, so I came downstairs, opened the door, and there was a freaking cotton mouth snake ripped in half on my welcome mat. I screamed and slammed the door, and immediately re-opened the door to find the snake no longer there...
I questioned my sanity about seeing the snake, how it got there, and how it disappeared so fast...but he told me later that day that it was his plan all along.
32. Hardly a Wholesome Breakfast
We broke up.
Two years and one move later, I look up from my bowl of cereal on my birthday and she is staring at me through the screen door crying.
33. Plot Twist
I feel ashamed sharing this, but I was the crazy ex. Have borderline personality disorder, boyfriend swore he'd love me no matter what and stand by me when things got hard.
He left. I reacted by threatening to hurt myself bad enough to end up in hospital if he didn't come back to make him feel as grim as I did. Not proud at all. Someone's gotta be the "crazy ex" though, I guess.
34. Diagnosis: Lies
Ex-gf faked cancer to get me back.
35. Man of Mystery
I dated a boy (27), because he was not a man by any means, for a little over 3 weeks. When I say dated, I mean we met, went out, and had intimate relations. Never officially dated. Some of the weird/crazy things about him:
- He had been engaged 3 times prior but didn't tell me this
- I'm 99.9% sure he was unemployed, but he told me he had a job. Yet he never went to it... or talked about... and nobody at the company knew who I was talking to when I called
- He gave me a set of rules to follow, including that I needed to spend time with him 4-5 times a week at least
After learning all of this, I became severely wary and told him we shouldn't continue dating. He became furious and claimed that it was my fault. Being the manipulative jerk that he was, I started to feel bad for bailing so quickly, however the following week he was seeing someone seriously so I'm pretty sure I dodged a bullet with that one.
36. Fast and Furious
My ex-husband started taking shots of Patrón, after popping a handful of percocets, while we were out to dinner with our children to celebrate his birthday. During the "celebration," he had his phone up his butt, and had been texting his brother the entire evening.
On our way home, with me at the helm of the vehicle, he decided it was a brilliant idea to throw his phone out the window at a stop sign. I put the car in park, exited the vehicle, retrieved his phone, and when I returned to the car I put his phone behind me, so he wouldn't do it again. You would've thought that I had shot his mother.
He began trying to turn off the car, started hitting the steering column, was screaming at the top of his lungs. It was... manic.
When we got home, he jumped out of the car, sans phone, and I told the children to stay put. I popped it in reverse and started moving down the driveway. That guy came hauling down the driveway like a banshee and jumped on the running board, face melted into a frightening state of rage, and tried to BEAT OUT THE DRIVER'S WINDOW of my car.
At this point, my children were in the back seat screaming and crying, and there was no way I was going to let them witness their mother get beat to a bloody pulp, so I threw the car in gear and hit the accelerator. He flew off the truck and I took off and didn't stop until I got to my mom’s.
He canceled both my phone and his, since I still had it. Turns out he had been texting his brother about going out for his birthday and "picking up chicks." You know. Since I wasn't going to put out.
He called the authorities and told them I tried to run him over and asked them to do a welfare check on the kids at my mom’s. The officers talked to the kids and saw the obvious marks on my window from his face and fists, and knew his story was trash. I left that day with the clothes on our backs. The kids were subjected to so much after I left, and I finally had it made to where they never have to visit with him without supervision again. It's that bad.
I'm now remarried to a much, much better man. He's a much better role model for the kids.
37. Beware the Blog
This isn't a story about a crazy ex of mine, but rather one of my younger brothers' that I ended up having to deal with.
Years ago, I developed a heavy following on Tumblr because I shared the fan music I made there. My younger brother (I think he was 13 or 14?) thought the website looked fun and made himself an account.
Now, I didn't know about this until it had gone really far, but one of my "fans" who was my age (which would have been 16 or 17) decided to initiate an online flirtation, and then a relationship, with my still-in-middle-school brother.
It made me really mad once I found out about it, but at the same time I knew that he would be encountering/dating girls all his life and nothing would be more wounding to street cred than having your "Tumblr famous" big sister step in on one of your relationships. My stance was to stay out of it...but I couldn't help but notice that my brother was going in and out of really severe moodiness, and I felt like it had something to do with her. So I looked up her blog.
This girl was definitely cracked—either that, or she was exploring a "mentally ill Tumblr persona": Posted constantly about voices in her head, and how she wanted to kill herself, but she couldn't leave "him" (meaning my middle-school-aged brother) behind, or how "he" did or said something that made her want to cut herself, or whatever.
So I did what any loving older sister would do... ran one of her selfies through reverse Google Image search to see if I could find a match on Facebook, ended up getting her full name, searched her name, found her in an online newspaper article for being on the Honor Roll, called the school, was put through to her guidance counselor, and described in detail the girl's behavior. I also emailed the GC screenshots from the girl's blog. GC said that behavior seemed very out-of-character for her (aiding my suspicion that the blog was "make-believe"), and that it would be addressed right away.
According to what she told my brother in her last messages to him, she was called down to the guidance office, her parents were there, she found out that someone had reported her blog, and they went through it in front of her, making her explain every post.
It was gone the next day, and she never made an effort to contact my little brother again.
38. A Toy Story
So get this... I dated a guy in my late high school years who was very reserved and very handsome. The first seven or eight months were unreal, I was so happy, and things were going great. Soon thereafter, he and I decided to tell each other our deepest darkest secrets. (10/10 do not recommend) He told me that when he was young, he used to cut holes in his stuffed animals and would have intimate relations with them. I had no idea what to think, but I honestly didn't feel like it was the worst thing someone could do, so I just let it reside in the back of my mind.
For unrelated reasons things got a little rocky in the months after. He became so jealous and overprotective. He would come up to my work and watch me for hours, he would drive me to and from wherever I needed no matter what, he would also get so upset when I spent any time away from him. When I did get the opportunity to hang out with friends, he would always buy me flowers or pillow pets and leave them on my car almost as if he was letting me know he was watching. This just got worse over the next 3 months and I figured it was probably time to end things.
I decided I was just going to drive over and just let him know things weren't working out, simple enough, right? Wrong. When he figured out what I was doing, he completely lost it. Punched holes in everything, broke whatever was in sight, and had a full-on episode. When I got to the house he was waiting for me in his truck which was completely ripped apart, might I add. I figured it probably wasn't the best idea to get out of the car, so I turned around to drive away and he busted out his truck window and then followed dangerously close to my car. After about a half hour, he finally let off and called me claiming he wrecked his truck. I went back to get him, but I'll skip the details on the endless crazy things he pulled that night. Needless to say, it was over.
A few months after the break up I decided it was probably a good time to get all of the things I had left at his house. It was mostly clothes, but I always left the stuffed animals he got me there just because. Long story short, I walked into his closet (The walls were still completely demolished from his episode) and I found some of the pillow pets he had bought throughout the relationship. I grabbed my favorite one (a grey elephant named Charlotte) and on the underside she was just covered in you-know-what. By covered I mean graciously glazed from multiple endeavors.
Side note: It is so weird typing this out. It never seemed as crazy as it actually is.
And that's all I have to say about that.
39. If You Liked It, Then You Should Have Put a Biscuit on It
An old college friend was coming over to visit, so she asked, "Where are your biscuits?"
"You know, when someone comes over, you should have an array of snacks, like biscuits, to offer them."
"He's not coming over for biscuits."
"Then what will you offer him?"
"I got some homebrew."
Two days later she says...
"Anyone who doesn't have biscuits doesn't respect friends and family," and breaks up with me.
This is not during the first two weeks of the relationship. This is when we were engaged.
Needless to say, I was an idiot to be with her, and we never married (thank God!).
40. Now the Only Thing I’m Sick of Is You
When I was 21, I started dating this guy who was about 30. I was one of those girls who insisted I needed to date older guys because I was sooo mature. Never mind the fact that he lived with his hoarder mother, had no job, no car, but plenty of "I'm so much better than everyone" attitude.
He was basically emotionally a teenager, and just a bad guy. He'd insult me constantly, publicly make fun of my appearance. He couldn't take no for an answer. He wanted to hang out EVERY DAY, when I was exhausted from ten-hour shifts at work.
One time when I was sick, I told him I couldn't pick him up that day. He insisted on it because he "wants to take care of me." Whatever. I agreed, drove the thirty minutes to pick him up, and back. He spent the whole day just complaining, "I'm bored." "Why won't you talk more?" "Don't you appreciate me coming over?" "Why do you want to SLEEP? Spend time with me. I didn't HAVE to do this." etc.
He was insanely jealous and suspicious. My yard at the apartment I lived in sloped down from the road, and the wind always blew down trash people threw out of their cars, including a cig butt in the driveway, and he saw it and accused me of cheating because it wasn't his brand.
Finally broke up with him. He stole and broke my iPod. He texted me nearly a year later to inform me that he was getting married to the perfect woman and was so much happier. Then six months after that, to inform me that she cheated on him and they split up. He wanted a hookup, I declined. He claimed he had intimate photos of me from when we dated and threatened me with them. I told him he was pathetic.
He's sporadically texted me since then, but I never reply anymore. Maybe my photos are out there somewhere, but whatever.
41. My Nightmare Wedding
A little late to the game but this is a gem.
My old roommate was the type of gal whose personal bookshelf was filled to the brim with wedding magazines and a few interesting titles included "making marriage work" and "Working through difficult relationships." She often went out with her girlfriends to try on wedding rings and wedding dresses.
That's all fine and dandy, but she wasn't getting married. Didn't even have a boyfriend. She BARRELED through hook-ups at a remarkable speed. I didn't think much of it until she hooked up with a friend of mine. He informed me of the following:
They started hanging out as friends, for about a week or so. Big surprise, they ended up sleeping with each other. Just once. He told her straight up it didn't mean anything, and he didn't think they should continue. She came home to me crying, absolutely bawling her eyes out because she didn't understand why he would "break it off so suddenly." A few days go by and I guess she broke into his apartment, cleaned the entire place and cooked him food. She waited at his apartment for several hours until he came home and said, I kid you not, "Hey honey, how was your day? I hope you don't mind but I cleaned up the apartment and made us some dinner before bed." I think he nearly pooped his pants.
42. Scarface Is Less Cool IRL
My craziest ex became a pretty big drug dealer while we were together. He really loved it too. Like this guy grew up watching mafioso films and genuinely got off on the idea of the adrenaline rush of being constantly paranoid, avoiding officers, and the bouts of brutality. It all happened so fast that I didn't realize how crazy everything was until I hear myself say it aloud.
He had guns everywhere, carried them all the time. He would completely lose his mind when he was angry. He kicked a guy in the face for harassing me and successfully scared everyone we knew. Nobody would look at me a second too long after that. I couldn’t do anything without him knowing about it. If I left his apartment after an argument he'd drive all over looking for me during which time he'd go from screaming profanities to crying and begging forgiveness from the street, from his car, over the phone.
He also had PTSD, which enhanced paranoia over everything. If you can imagine waking up to your loved one facing the door with a pistol in his hand ready to kill the next person that knocked, welcome to my life. I was astonishingly calm throughout it all. I guess I forgave most of it over the PTSD, which I really wanted to help him get past. He didn't sell substances in the beginning. It was the bulk of why we broke up. He was actually really great at first. We really loved each other. Last I heard he was living the dream and getting into serious trouble.