Dating can be painful. Yes, sometimes if you get the right person and you hit it off, it can be a great time, even life-changing. But, a lot of the time dating is an exhausting ordeal. For those that have had the privilege of never having a bad date, congratulations, but for the majority of people, it is something that has happened at least once. But a horror story can be rare. So, here are some of the worst dating horror stories... ever.
Don't forget to check the comment section below the article for more interesting stories!
#1 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.
#2 Falling For The Friend
I had no car at 17 but thought I would be creative about taking a girl to a movie without involving my parents:
I invited this girl I had a crush on to come to the movies with me and two guy friends. We sat in the back seat together, and sat next to each other at the movies. For the most part, my friends left us alone and it seemed like we were on a quiet, awkward, conversation-less first date. I was pretty lame but tried my best to keep her interest in the few moments a movie-date provides.
But on the ride back to her house, my best friend happened to play some music she liked on the stereo and they started talking. She immediately opened up and the two of them hit it off instantly (while I was sitting next to her in the back seat, silently raging). She dated my best friend for a year after that. 
#3 Playing The Wrong Tune
Brought my date to my friend’s house. Friend pressures me into playing guitar. I played “Needle and the Damage Done”; first thing that came to mind. Why? Dunno. Turns out her brother had died of an overdose not long before. Awkward & chilly for the rest of life.
#4 Ending the Date
I was driving to the movies on a first date with a hot girl and we saw a feral cat get destroyed in traffic. The poor thing got a paw run over first and it was doing this crazy leaping thing and people WERE NOT STOPPING and then a truck finished it. Game over, date finished, we went and sat on her couch for an hour and then I went home.
Poor little cat.
#5 Hummer of A Date
Took a girl out on a first date in a rented car. I gallantly open the passenger door for her, she gets in and motions that she’ll close the door herself. I agree with this, so I circle around to my side just as a Hummer zooms by and SMACK! Takes the passenger door right off and doesn’t stop. Confirms everything I ever believed about Hummer drivers.
Girl is paralyzed with shock and horror, asks me to take her home. Rental place finds some reason that my insurance doesn’t cover this damage. Still paying for it. FML.
#6 Talking Kids
He asked me on a date, I knew I didn’t want to date anyone but told him we could go to dinner as friends (as we had mutual friends and kind of knew each other), and he agreed. While we were at the restaurant he started talking about what our kids would look like—I’d change the subject and he’d change it right back.
THEN, he told me about how while working at one of his previous jobs he stole $1,200+ and got away with it by telling his manager and the cops that he was robbed.
#7 A Long List of Horrors
The following are all things I found out on the first (and only) date. Each individual one of these things was a massive red flag in and of themselves.
- He mentioned that he had done a B&E to somebody’s house to find stuff to sell to buy alcohol.
- He seems to be an alcoholic.
- He told me he robbed a liquor store.
- He says he has anger management issues.
- He is convinced that horror movies are accurate depictions of real events.
- He claims that “the moon is his guide.”
- I asked him what the that meant, and the explanation was messed up enough to merit being messed up thing #7.
- He stole somebody’s wallet after sleeping with them.
- The aforementioned individual in #8 was his dealer (this is an inference I made).
- He went to a mental institution when he was 15.
- He has a history of hardcore illicit substances use (although that kinda is a given considering everything else).
- When a police car passed us on the road, he freaked out.
- There is probably a warrant out for his arrest.
- He threw somebody down a flight of stairs because they slapped him.
I wish I was making this up.
Pinterest
#8 Guilt Trip With The Cops
So we’re still in high school, and we’d been hanging out forever, really liked each other. He’s a pretty decent nerdy guy, we play Starcraft together all the time, have a couple of classes together. He takes me to a Magic tournament.
Cool! I register and I start playing. I advance, and he throws a hissy fit after I beat him… and refuses to drive me home. The guy behind the counter guilts him into taking me home, and we’re about half-way through the awkward silence home when he gets pulled over by the cops for speeding. Instead of cooperating, he throws a fit and starts yelling.
Officer asks him to step out of the car, and he eventually does. I’m in tears, so the nice officer calls my parents to come and get me from the side of the road, because he’s taking DateGuy to the station for belligerence and, as he said, “Totally ruining your night.” I had to answer a ton of questions with the guy sitting in the back of the cop car, glaring daggers at me.
Worst date I’ve ever had, and I had to continue taking classes with him until the end of the year. We never spoke again.
#9 First Date With Dreads
I was a 20-year-old working at an animal shelter. She was 29. She was a white girl with dreadlocks and didn’t shave her armpits, but she was pretty hot for her age. She was also quite direct and asked me on a date (my first date ever).
For our first date, she took me to eat clam chowder somewhere, drove really fast in her Trans-Am, told stories about how she used to shoplift thousands of dollars from Nordstrom’s and outran the cops once in her car. She was BLASTING “Punjabi MC” on the stereo when some black guys pulled up next to us and laughed. She said “ok man!! ok!” and switched it to Eminem and sped off.
After that she wanted me to show me her paintings at her house. I gotta give her credit, she was productive. The entire house was cluttered with paintings. She showed me various paintings and told me the stories behind them. One painting was of herself as a girl, stabbing her genitals with scissors. She said, “I thought he would stop touching me if I were less of a woman.”
I was young, naive, and put up with it all, loving the fact that someone noticed me enough to take me on a date. She drove me home, stopped in front of my house and asked me if we were going to have a goodnight kiss. I said, “I Dunno, I’ve never done that before.”
She said, “Put your head back and close your eyes.” And she gave me a peck on the lips. That was my first date and kiss. I never saw her again because she had to take care of her cancer-stricken uncle who lived on a houseboat. Awkward date in retrospect.
#10 Nope, Not Your Daughter
Long story short. Christmas party went well. Met a girl. Woke up in her apartment, in her bed, naked on top of the covers. Woke up because a man in the doorway was angrily asking me, “Is that my daughter?” He had come to pick her up for Christmas vacation and her roommates let him in. I answered, “No” by the way. Seemed the only smart thing to do.
#11 Best Friend Saves The Day
I went out with a guy and we ended up going shopping at the local mall. All the while, he is really sweet and hugging/holding me. After about two hours there, we run into someone who is apparently his current girlfriend, who happens to be with another guy. Miraculously I also ran into my best friend and was able to survive the incredible awkwardness that was that moment.
#12 A Fork Of A Time
I had a friend who took this girl out to dinner for a first date. It was a disaster right from the start as this girl spent the entire date on her cell phone. Being the nice guy he is, he just decides whatever we’ll get this date done with and never call her again. At one point he gets up to go to the bathroom and on his way back, notices her sweater had fallen off the back of her chair.
He bends down (putting one hand on the table for support) to pick it up and feels a sharp pain run through his hand/arm. He looks up and she had stuck a fork into his hand and, while still on the cell phone, simply goes “oh it’s you” and continues her phone conversation. He found the waiter, paid for his half of the meal, and never looked back.
#13 Bringing Race Into The Date
Two and a half years ago, I went to a concert at the Fillmore in San Francisco on a first date with this curvy blonde. We got dinner at a little Italian place, then we took a walk around Japantown while we were waiting for the doors to open. She starts spewing a wave of anti-Asian racism, including her desire to “end all the Chinese boys.”
My best friend since fourth grade is Chinese. After the concert, I stuck a twenty in her hand and told her it was cab and BART fare, so she could find her own way home.
#14 G.I. Jane And Neediness
He wanted to watch a movie at his house. Turns out, he wanted to watch G.I. Jane. Turns out, it’s his favorite movie. Turns out, he gets so pumped when watching it he wears his army fatigues and spontaneously does pushups every five minutes. Then we go for a walk and he insists on holding my hand and practically hanging on it for the entire walk.
Finally, I get to my house and send him home, relieved to finally be alone. Five minutes later, I hear something hit my window. Then again. He’s outside, throwing rocks at my window. He tells me he loves me, and gazes up at me with a grin. He had to see me again! I tell him, “Go home!”
I think about how I’m going to break up with this extraordinarily needy dude. It digs at me all night. In the morning when I leave for work I find flowers under my windshield wiper, and a poem. First dates can be gruesome.
#15 Surprise! Dating A Coworker Goes Bad
Last year, I started screwing around with a coworker of mine. BAD IDEA. We decided to go to a party as our first date-like thing. The party was at her house (she had like six roommates in this giant house). Now, I’m not really a big drinker, but these people (all of whom are well into their 20s) were just getting schwasted off of Barton’s Vodka. I’ve never seen a more childish abuse of alcohol.
Yada yada yada, everybody at this party (25 people or so?) started drinking at about ten, and were all passed out in piles of their own vomit all around the house, high-school style. The girl I’m with, after throwing up on her bed, drunkenly begs me to stay and take care of her. Because of my hatred of immature drunk people, I simply leave (kind of a jerk move, I know).
The next day my boss talked to me and said that I wouldn’t be working with her anymore because she threatened to fill out a harassment case or something against me. Whoa!
Worst date ever.
#16 Hospital Waiting
I had a dud first date—we had nothing to talk about, and none of the social skills or inclination to make small talk. We made it halfway through the second drink before both abandoning the idea. I walk her back to her car—she collapses on the way. I call an ambulance, and end up in the emergency waiting room wondering exactly what my obligations are to a girl I don’t know.
I stick it out for four hours until she’s discharged. I ask her to call me when she gets home, to make sure she gets there ok—she doesn’t call.
#17 It’s A Small World
Second date. Meet a girl at a nice dimly romantic bar that she picks. We talk for an hour, everything is great. Suddenly she starts crying saying that she can’t take it, she’s hung up on some guy. She proceeds to attempt to dump all this stuff on me about some guy she’s been seeing but they took a break from each other and she thinks he’s been hanging out with this other girl.
I ask the guys name and almost soiled my pants because one of my friends had actually been dating him. I mention this to my date and she just loses her mind even more. Crying, getting pissed, and all the while I’m in shock.I got up like five times lying that I had to piss just so I could go to the bathroom and be like WTF.
Finally, I come back to the table and just say I gotta go. She calms down and apologizes and I bailed out. We stopped talking soon after.
Pinterest
#18 Cat Conversation
It was a speed date. He talked about his dead cats, all of them from his past, for the entire five minutes or whatever. I’m not sure he knew my name.
#19 Seeing Siblings
I was on a date with some girl in high school and I ran into her sister (e dated her like a year before) with her current boyfriend—my brother. Awkwaaaaard.
#20 Turning To The Feet
Was set up on a blind date by a coworker. Things went reasonably well—ok conversation, he seemed to be genuinely nice. My co-worker and her boyfriend double dated with us for moral support. We went back to the co-worker’s house after dinner to watch a movie together. That’s when things got weird.
Co-worker and boyfriend left the room to give us some “alone time.” Immediately, my date tried to kiss me. It was one of those approaches with his tongue hanging out. I nicely rejected the kiss, saying it was too soon for that type of affection for me. So he shifted his attention to my feet.
I was wearing open-toed shoes and he grabbed a foot in his hand and asked if he could rub my feet. I declined and he began to beg. Told me that he loved feet and would love to suck on my toes. I declined again, started to get a bit scared. He made a last ditch effort by asking if he could just sniff them once. I gathered my things and left ASAP.
He followed me to my car and tried to beg me in a baby-talk voice to come back, me and my “widdle piggies” (toes). I kept expecting a camera crew to pop out from behind a tree proclaiming that I had indeed been “punk’d.” I was as nice as possible about everything, citing that I just needed some time to get comfortable with someone before becoming affectionate.
I pulled out of the driveway in such a hurry that I squealed my tires a bit. I had no intention of seeing him again since he had violated my personal space so much. I (probably wrongly) passive-aggressively ignored his phone calls and myspace messages. He couldn’t take a hint though, and called 20 times in one day.
I finally manned up and told him that I wasn’t interested in pursuing a relationship. He immediately got nasty, called me a tease, and told me never to contact him again. Weirdest date ever.
#21 Terrible Time
Took a chance on a questionable fart when she was in the bathroom. Soiled myself.
#22 Parental Pick Up
He called 20 minutes before he was supposed to pick me up. Told me he’d be a couple hours late because he wanted to play basketball… the time he was supposed to get me rolled around… no show… twenty minutes later a car pulls up and his mom gets out… (keep in mind we’re freshmen in college).
He sent his parents to come get me. 20-minute drive to his house in the car. Alone with his parents. He proceeded to talk about the girl he was in love with for the rest of the date and ended it with an awkward hug stating that it wouldn’t work because we lived too far away.
#23 Feeling Her Brains
I was to meet my girlfriend in a building near midnight for a date. When I got to the predesignated room in that building she directed my attention to a jar on the table. It had a human brain in it. She told me to don gloves and take the brain out of the jar. As I was holding the brain, it seemed very small.
I asked, “Is this a child’s brain?” She said, “Yes.” I felt a shiver run down my spine as I held the weight of the child’s brain in my hands. I started to imagine what this child was like before it died. What did its face look like? What kind of personality did it have? She interrupted what had become a rather chilling reflection by telling me I had to help her cut up the brain before midnight.
We cut into the flesh of the brain that used to hold memories, feelings and dreams. Now it was cold and lifeless as my date became very attentive to every detail of structure that our knife revealed as we cut the brain apart. When we finished, I put the pieces back into the jar and we left for the rest of our date.
She was a medical student and I often had to help her study in our dates. It was the only date I ever had in which I felt genuinely ghoulish for part of the date.
#24 Twilight Times
I met a girl in a club whilst working as a nightlife photographer—you meet a lot of girls that way, it’s a good icebreaker. She was pretty, sweet and funny, and we kept bumping into each other throughout the night as I worked. Ended up finishing work and getting to chat to her a bit, things were great, and we ended up going back to her place for a bit of drunken rumpy pumpy.
When we got into her room it was like a normal student room, posters on the wall etc, typical girl stuff, y’know? Twilight poster, calendar of a boy band, some frilly stuff… all that. Quite cute. Anyway, we got down to business, and we were nearly naked when she whispers into my ear in the most seductive way possible, “Bite me like Edward.”
I had my clothes on and was out of the door faster than you could even imagine.
#25 Bad Drunken Decision
I was out one night, and had beyond enough to drink. I went to a cafe next door to the bar, grabbed some food and hung out for a while. This guy walks in. He’s kind of cute, so we start talking and I invited him to share my sweet potato fries with me. One thing led to another, we went outside, made out for a while and then we took a taxi back to my place.
Everything seemed fine until I tried to drop him off the next morning. I asked him where he lived, and he kind of avoided the question, just giving me directions. To the local homeless shelter.
He was homeless. And he admitted he was homeless because he just got out of jail. For assaulting a woman.
I had given him my number before any of that came out, and he called constantly. After a day, I had to block all unknown numbers on my phone, because (being homeless and all) he called from a different number every time.
It was miserable, and it took nearly a month for the messages to stop (thank god for visual voicemail).
#26 You Should Have Dropped the Girl Instead of the Class
Left her dorm room to go get to a canceled class. Decided to go back to her room to hear her hooking up with another guy (she was very loud). I knocked on the door and she answered thinking someone was going to ask them to keep it down.
#27 As Long As You’re Over It
I’ve been cheated on and cheated with but never cheated. Each time the cheater just fessed up and told the truth. Except for my sixth-grade boyfriend, Chris. I found out from everyone else in my middle school that he made out with some skank at the movie that he had invited me to but I was busy. Screw you, Chris.
Totally over it though.
#28 The Joke’s On Her
I canceled on a party her friends were having because I worked late. My boss let me out a few hours early because it was dead. So I went to the party. Got there and asked her cousin where she was. Her cousin said, “oh, she’s in her car out front on the phone.” As I walked away to go to the car her cousin panicked and said “NO! WAIT! SHE’S IN THE BATHROOM!”
Me knowing she was lying, I jogged to my gf’s car out front. Looked in the window and she was pantless doing "favors" for two other guys in the back seat.That was ten years ago. Now she’s a mother to four fatherless children and I’m engaged to her beautiful, latina ex-best friend.
#29 What Happens in Vegas Doesn’t Always Stay There
I doubt I’ll ever get the truth on it, but my ex (we were together for six years, engaged for a year and a half) went on a work trip to Vegas, we were eight months away from our wedding, half of it was paid for (venue, videographer, photographer, flowers, and catering all had deposits, dress was bought and paid for)… And when she got back from the trip she said: “I don’t love you anymore.”
Kicked me out of the apartment and had a new guy move in three weeks later and got engaged to him a few months ago (about a year and a half after the split). Either she had been cheating for a while or thinking about it or both. Either way, it was the best thing that ever happened to me, while simultaneously being the most painful thing I’ve ever experienced.
I’m MUCH better off now and MUCH happier and healthier as well. I’m finally over it (almost two years later) and although she hurt me pretty freaking bad, I look back and realize that I hated myself (I was severely overweight) and wasn’t in any position to love someone the way they needed to be loved because I didn’t love myself.
Life will dump on you, and you can either wipe it off and learn from it, or sit and play in it and get used to the stench until no one wants to be around you. It’s your choice!
#30 Moral of the Story
Caught my ex-fiancee on New Year’s. I posted pictures of us, exclaiming how I was excited to spend another year with her. Sadly enough, her other boyfriend saw the post I tagged her in. He was awfully upset as well. I still sympathize with him because I know how it feels.
Don’t cheat on your partner. It tears people up inside.
#31 Definitely Getting the Message Across
My ex’s friend took a snapchat of my ex (while she was still my girlfriend) hooking up with a dude at a party and sent it to me.
#32 Who Are You Gonna Believe, Me Or Your Own Eyes?
Go to the gym, no headphones! That’s cool, house is five minutes away. Pull up in front of my house and see work buddie’s car out front. Walk in house through open garage. Son coloring at kitchen table. Ask him “Hey bud, where’s your mom?” He points at the stairs. Walk to stairs to hear moans and movement.
Up to this point I had suspected the worst but never had proof. Knew I had to go look and catch her or she would say I was overreacting and tell me it wasn’t what I thought. Walk upstairs and hear them in the spare bedroom. Walk in the room and say “well this is awkward.” They freak out and try to grab clothes and tell me nothing is happening.
I walk out to my car and have ex-buddy chase me out and tell me to hit him. I go to my command (I’m in the military) the next day. Report him and have the command force him to call his wife that day and let her know. I am now divorced and much happier!
#33 Way to Break the Relationship
Was on a “break” with my girlfriend at the time. Got a text from a girl that I had mutual friends with and we knew each other kind of well—started having dirty conversations, talking about sleeping together, etc. Turns out my girlfriend had gotten a burner phone with a different number and was the one sending me the texts the whole time. She was not pleased.
Mashabale
#34 A Conversation Waiting to Be Discovered
I picked up his phone to change the channel on Chromecast. It unlocked and opened the Messenger app where he was making plans with my roommate to hook up while I was at work the next day.
#35 A Little Too Enthusiastic
I was smiling at my cell phone too much. She caught on.
#36 Get Your Head in the Game
We went out to lunch, she wasn’t even able to hold a conversation. I had to repeat myself multiple times because she was so enticed in whatever hilarious thing she was reading. Asked her what was so funny and she just kept saying nothing. As I was on my way to dropping her off at her place, her phone, sitting in the cupholder, started ringing.
The number wasn’t registered in her contacts. I went to answer it expecting a telemarketer or someone who simply had the wrong number with the intent of messing with them to have some fun. I went to grab the phone. She has never had a problem with me answering calls like that before, she even found it entertaining. Anyways she freaking attacked me, started screaming at me, and ripped the phone from my hand.
We didn’t speak for the rest of the ride, needless to say, it was obvious what was going on. Shame. Turns out it was my only friend at the time. Lost two people I thought I could trust that day.
#37 A Not So Holly Jolly Christmas
My fiancé left me two days before Christmas. She told me she needed to move out for a bit and get space. That she was moving to her friend’s house. This went on for a week, until, because we have a family Apple plan, I looked up her location. And she was not at her friend’s house…
I’m now a single dad of a one-year-old and she’s moving out west with him…
Merry Christmas.
#38 A Love Hate Relationship
My dad was recently caught cheating on my mom after 27 years. While using his laptop, my mom noticed that Facebook said: “Hello Mike Long, can we log you back in?” My sweet mom still had no idea he was cheating, until my teenage sister broke it to her that he’s using a fake account. That only opened a whole other world of nasty surprises. Love you dad, but I also hate you.
#39 Sometimes It’s Not Even a Secret!
I’m a live in nanny and the parents are going through a particularly nasty divorce (mostly because she’s totally insane). Either way, she decided one day that she didn’t give a damn anymore, and started bringing this dude she’s been sleeping with over to the house, sometimes even while the Dad is home.
She says “they are just friends,” but I’ve caught them making out on several occasions. Which she portrays, of course, as that “he kissed her,” “she didn’t want it” blablablabla. Really Amanda? Then why did I watch you go sit down on his lap and stick your tongue down his throat? She’s also encouraged the kids (while the Dad isn’t home) to call this new guy “daddy.”
Thankfully the Dad has finally realized just how crazy she is and is getting a divorce, but as this is all pretty recent, we haven’t found a new place yet. Thank God he’s going for full custody, and that the kids are still really young (and that I’m going with him and the kids). It terrifies me what those kids are going to have to deal with in their lives because she is their mom.
She is an incredibly selfish, narcissistic, piece of trash excuse for a human being, and I hope all this karma comes back to bite her on the behind really hard some day.
#40 Throwing a Curveball
Not sure who I am in this story. Worked with this girl, in different departments at a huge company. We got friendly and hooked up a few times. So one day we’re out at a bar. I turn around and am face-to-face with her. Without missing a beat she introduces me to her husband. I don’t know how but I played it cool.
#41 Plot Twist
It happened to a friend of mine. We were all on vacation (about seven friends) and everybody was drinking. We were the only two who didn’t. He managed to snag his girlfriend’s phone while she was passed out and pulled me to the side. He said, “she’s cheating on me, some guy named Joey has been texting her and meeting her after work for a hookup every day.”
We ended up searching for names and mutual friends via Facebook. Turned out Joey was a girl.
#42 Is the Excuse Any Better Than the Crime?
Found a condom clearly used for getting it on. He ended up blaming it on his mother, who didn’t live there. Happy to call that jerk an ex.
Pinterest
#43 Gridlock
Was dating a girl in college and didn’t think she was cheating. Another guy she was dating thought she was. He found my info in her phone and texts me about it. He wants to confront her. We both meet up at her place while she isn’t home. He’s a nice guy and we honestly got along pretty well for the half hour we talked before she arrived.
She saw us both as she drove up and the look on her face was shock. By the time she got out of her car she was crying but didn’t say a word to us. We went in her apartment and her roommate acted as the mediator but it didn’t really get anywhere. Me and the other guy were pissed and wanted answers. We weren’t getting any so we both gave her some choice words and rolled out.
#44 Now That’s an Entrance!
While at uni I walked in on an argument between my gf and her housemate as the housemate shouted: “at least I’m not a whore who sleeps with everyone when she goes home!”
Turned out she was sleeping around.
#45 Google Knows Everything
I signed into her Google Account to check her emails (She forgot her password so I had to reset it). I checked her Google Maps history and her most recent visits were at my best friend’s house while I was away for work.
+1 for Google Maps.
#46 Scheduling Conflict
Had been with this chick for about one year. At our school summer camp, a guy from the class above me came up to me and straight up said: “Hey, I hear you’re so and so’s new boyfriend, I’m her ex and just wanted to say hello.” I didn’t really know what to make of the situation but for some reason, I just asked when they broke up, and he said: “oh like one month ago.”
Needless to say that relationship was over quickly.
#47 You Don’t Say?
He was basically living with me because we just had a baby, and he hadn’t been home for a couple of days. His best friend informed my best friend that he had no idea we were even together because he has been with this other girl for the past couple of nights on his friend’s couch.
#48 We Feel For You
This is so recent (a week ago). I went to the spot I first took her to on the ship we worked on to surprise her, and she was on top of another dude. They looked me in the face and laughed when they saw me. I absolutely loathe infidelity, and feel for all the victims of heartache.
#49 Wrong Place, Wrong Time
I was at a party with a group of friends. I was standing behind my best friend talking in a group when my friend all of the sudden gets a text. I look at his phone and it’s my girlfriend’s full name and her asking when he is going to be over. She was supposed to be out of town at her mom’s house.
#50 Holden Would Be Proud
My best friend lived in the family’s old vacation trailer behind his house (back in the 90s). I arrived with a twelve-pack, opened the door and there was my girlfriend. She was standing full frontal (not a stitch on) and he was in his boxers. Later he told me “Nothing happened.” JD Salinger had a term for that kind of guy, it was… PHONY.
YouTube
#51 If He Can Make It There, He Can Make It Anywhere
He went to NYC on a business trip and his phone was constantly going straight to voicemail whenever I called. When I finally got in touch with him he said that he was having a hard time getting a signal… in midtown Manhattan. So I called his office and asked for him and they were totally confused. I turns out he was in another state visiting someone he met on the internet.
#52 Love is Not a Game
I’d finished doing the dailies on my WoW character, and I knew he wasn’t going to be home for a while so like many times before (with his permission) I logged into his account to do dailies for him.
Then the PM’s started. Very explicit PM’s. Not only was he cheating on me in a game, but there was one girl who was talking about things outside the game too. I admit I played along for a while to see what was going on.
After that, I told her who I was. It all ended rather badly, between her and I, him and I, and him and her.
#53 She Can’t Keep a Secret
She kept telling me how she wasn’t happy with us being apart at different colleges and how she met these really nice people. Turns out one of them had a thing for her and they made out one day. She broke down and told me immediately. She wanted to keep hanging out with him and I was obviously not okay with that.
I visited her to patch things up. Dumb of me to try to salvage it in hindsight. Not long after, she meets another guy in one of her classes who happens to be friends with some of her other friends. I immediately got a bad vibe but I just told myself I was being paranoid and she said nothing would happen. Yeah, apparently they hit it off a little too well.
Long story short she tells me about this one too after I kept asking. I ended up trying to patch things up again. Screw everything about how that relationship ended. Actually, in hindsight, if my relationship hadn’t ended so poorly, I wouldn’t have met some of the fantastic people in my life today. Now that I think about it, I actually haven’t had any contact with her since the breakup.
#54 It’s the Thought That Counts
20 or some odd years ago I caught my ex in bed with another guy. On Valentine’s Day. With a dozen roses in my hand. What a horrible person. Fighting would get you kicked out of college, so I told the much smaller guy that as soon I saw him off campus some day, I’d end him.
Fifteen years and worlds later, I’m at an engagement party at a bar, and some friends come up and tell me the guy over there is extremely scared of me and thinks I’m going to end him. I look over and couldn’t stop laughing. It was so far in the past, but for some reason that guy remembered it like I had sworn an oath to avenge my family. It felt good. His fear was redemption enough.
#55 Hunting for Problems
Brother of mine caught his wife. Her phone would always be going off and she would hide it. He got curious, looked into it, and found some guy had been texting her for a few months. She said she was going to stay home because she had to catch up on homework over the weekend. My brother and I went on our hunting trip and he told me about it.
We never left the city, we went to my house and stayed there till it got dark, then drove back to his neighborhood in my neighbor’s car. She sent him a picture of her at home saying she was going to go to bed early that night. Well, we snuck close to the house after a car parked down the street and a guy walked to the house and let himself in.
My brother was fuming at this point and wanted to beat the heck out of the guy. I settled him down and told him to think about the long run. We snuck up to the house and using the night vision camera got video of them bumping uglies in the living room. My brother wanted to confront this guy at this point so… I did something messed up and called the cops. I said I heard a lot of yelling from the house and asked if they could go check. It kept my brother from messing with the dude (a coworker of hers).
Cops show up, take statements. We leave and the next day he pulls her iMessages off the email account and talks to a lawyer. We give the lawyer the messages and when we show up five days later from our “hunting trip,” he calls her and says he got something wild and wants her to come out and see it.
When she comes out he gives her divorce papers and kicks her out of the house. She had the police do a civil stand by while she got her stuff a few days later. House was his before they got married so all she got to keep was some stuff they bought together and her car. No kids and the prenup nullified the alimony she could have gotten as he made way more money than her.
The guy she was sleeping with had a record. We saw her a few months later, she tried talking to my wife and said she missed my brother and she was sorry, the guy and her broke up shortly after the divorce.
#56 Did He Get an A+?
I caught my boyfriend of two years. He had asked me to proofread his paper on his Mac and the text messenger popped up in the right hand. He was sitting in his bed texting some girl “goodnight, I love you” while sitting right next to me in his bed. I deleted his entire paper, wrote “Who’s Marissa?” saved it and told him it looks great and left.
She was his girlfriend of eight years who lived next to his parents two hours away.
#57 The Joke’s On You
I once commented on a social media post and made a joke, saying that I went back to a girl’s house to play Uno and talk about politics. Clearly just a harmless joke. Then one day, I get into an argument with my girlfriend and she screams out “AND I KNOW YOU WENT BACK TO THAT GIRL’S HOUSE TO PLAY UNO AND TALK ABOUT POLITICS!!”
That moment was so ridiculous that we could never recover.
#58 Comical
My boyfriend really looked up to Captain America, who always did the right thing and stuck to his morals. One day, he said that he wasn’t happy with me because I was not living up to Captain America’s standards of good behavior. That was it for me.
#59 Point of Contention
Mine wasn’t anything crazy or bad per se. It was just that she wanted kids, and I didn’t want kids. I realized at a certain moment that we would never be able to get past that, so I had to stop wasting her time.
#60 The Blame Game
He was the best boyfriend one could ask for the entire time we were together, but when he started blaming me for all the wrongs in our relationship, constantly, that was the moment when I said to myself “I’m out.” There were times when it was his fault, but he just wouldn’t accept his mistakes. I loved him, but if you keep pushing me down for past mistakes and can’t agree that we need to work together to fix things, the relationship will get toxic and neither of us will be happy continuing it.
#61 Meet DefinitelyNotYourGirlfriend123
The moment that ended my relationship was when I discovered that my ex-girlfriend had secretly made a Reddit account without telling me, and started commenting on posts of mine asking how I felt about my girlfriend. Any relationship with that little trust and that much deception is in trouble.
#62 One Trick Pony
What ended my relationship was the realization that a relationship should not just be purely physical, which is what ours was. There was nothing more to it than that for us. All I did was fill his hunger for physical contact all day every day. Not being able to even visualize a relationship with him beyond the physical ended it for me.
#63 Liar Liar Pants On Fire
I knew I was done with him the second I caught him lying. I don’t like lying. If you lie, I will catch you and I will feel uneasy. Don’t lie to me, people.
#64 True Colors
I overheard my girlfriend telling a friend that she wasn’t really interested in me long term and just saw me as a familiar old friend to have some fun with for a bit. It was hard, but I couldn’t go on dating her after hearing that.
#65 Pronoun Trouble
My moment of truth was when I told her I loved her for the umpteenth time, and she said, once again, “Who are you trying to convince—me or yourself?” This was from a woman with whom I was planning to marry. It just hurt me so much that she could think that way after all we’d been through.
I never recovered emotionally from it and broke off our engagement some months later as a result.
#66 Verdict: Not Guilty!
My ex-boyfriend always apologized for the way he mistreated me and said that he was a lonely child since his birth, and that his parents never paid attention to him. I had always thought my love would be enough for him to feel secure eventually. I felt responsible for him. When I finally realized that I wasn’t, I ended the relationship.
#67 Making the Decision Easy
The day before Thanksgiving, she told me she wasn’t actually in love with me anymore and hadn’t been for a long time. That pretty much sealed the deal right there…
#68 A Small Miscalculation
When he admitted, with a sigh of relief, that he had recently hooked up with my sorority sister while I was gone for work. Immediately, he hugged me and told me how much better he felt now and said he knew that we would grow stronger together from that point on. He was wrong. It was like one of those movie moments where the camera should have panned from his relieved smile during the embrace to my dead eyes.
#69 The Party’s Over
My relationship ended when I caught my then-girlfriend cheating at a party. I was visiting her from out of town and was having a pretty fun time. After a while, I told my girlfriend I needed to turn in, and she was like, “Yeah, go crash in my bedroom. The party’s basically over anyway.” So I got into bed and closed my eyes. Then, I noticed that it had gotten really quiet in the living room. Like, no one was talking at all.
That was a bit odd, so I got up and walked out…and my girlfriend was swapping saliva with some guy on the couch. They were so intent that they didn’t even see me standing there looking at them until I said “What the heck??” out loud. I’ll never forget her jumping away from the guy and wiping her mouth with the back of her hand, then saying “It’s not what you think.”
Oh really? Then what, precisely, was it?
Despite some dramatic attempts to keep me there, I took off and didn’t look back.
#70 The Fruits of His Labor
Mine was when he confessed to me that he had contracted herpes from some girl he was hooking up with while still in a relationship with me.
#71 If at First You Don’t Succeed, Try Try Again
There were many moments which temporarily ended our relationship a long time back, but I kept bringing it back to life as I could not come to terms with the fact that my first relationship would not be up there on the board of successful relationships. After a few years, when I became more mature and realized that feeling “perfect” in this way was not as important as my overall happiness, that was the big moment for me.
#72 No Pain No Gain
I was done when he refused to go to counseling with me. That was my proof that he wasn’t interested in trying to repair the relationship. It also showed me that he didn’t respect me enough to want to improve our situation. I walked away, never looked back, and have never regretted my decision—even 17 years later. We are both living happier lives now because of it.
#73 Failing the Test
We were together for a year and a half, but then things suddenly changed. He would be disinterested in talking to me and would give me less time. I didn’t argue about this because he had exams coming up at the time and I didn’t want to disturb him. It was only after his exams ended and this routine still followed that I realized things were not going back to the way they had been before.
#74 Acts of Dog
I asked my ex to please stop hurting my dog, which he had started to do for no apparent reason. He refused. He then accused me of hitting him out of the blue. I know I did not. He was “gaslighting” me, a specific form of abuse that is very mentally harmful. At first, I questioned if I actually did it and forgot. Then later, I figured out what was going on and knew I had to go as soon as I could afford to move to another place. I am now gone and happy.
#75 The Dreaded Phrase
The moment I knew my relationship was over was when I heard the words “We need to talk” come out of her mouth. I have a feeling I’m not the only one who’s had this experience…
#76 Rules and Regulations
It was when I realized that it wasn’t normal for a boyfriend to have all the “rules” that he had for me and expected me to strictly follow. I was to have no male friends, to not talk to any family members who didn’t approve of the relationship, to walk with my face down looking at the ground and never make eye contact with strangers, etc. No thanks!
#77 Getting Deep
I knew I should end my relationship when I had a sudden and clear realization that every time I saw her, it felt like I was just doing something I had to do rather than something I actually wanted to do. It took four years to get to that point, but there was no going back after that moment.
#78 Doubts Confirmed, I Guess…
When I said I was having doubts about the relationship, and he responded by trying to end me. He literally started to run my car off the interstate. It seemed like reason enough to immediately end it and get a protection order.
#79 Now or Never
After many months of romantic talks and walks, I said that if she gave me just a few years, I would have the money to get settled down and marry her. She then said that she didn’t want to have to wait that long. From that point on, it was all downhill. We went for coffee a few days later and she told me she didn’t think we were right for each other. I was devastated.
#80 Busted!
I fully admit it was my fault, but nevertheless, my relationship had one clear moment when I knew it was over.
It was when my girlfriend told me that she had secretly installed a camera in the shower to try and catch me cheating… and succeeded.
#81 Alcoholics Identified
My wife always had a drinking problem but I tried to not judge and just live with it. Until one day when I came home from work to find my daughter saying she couldn’t wake up mommy. After ten minutes of trying to wake her up and finding an empty bottle underneath the couch, I realized that I can’t be with a person like this and neither should my daughter.
I have recently started the divorce process. It’s going to be messy, but it’s worth it to make sure my daughter won’t be traumatized like that anymore. Wish me luck.
#82 If That’s a Minor One, I’d Hate to See a Major One
The second time we had ever gotten into a minor argument, she reacted by cutting herself and throwing a tantrum. It was so bad that I actually ran and locked myself in the closet. I knew instantly that this could not continue.
#83 It’s Not What You Know, It’s Who You Know
My moment was when he fell asleep next to me, and a text message arrived on his phone. Curious, I look and see who it is from. The contact was named “Babe
.”I’m horrified. It must be a joke. I read some texts to see the things they were saying. I found a message of her saying, “You make me the happiest girl in the world.” Unbelievable.
That’s a big no for me, goodbye!
#84 Don’t Let the Stars Get in Your Eyes
In hindsight, I could kick myself for being so stupid and naive during my long relationship with my ex. We were together for 17 years. We were both 18 when we met and it felt like love at first sight. I fell hard for him. He was very handsome, intelligent and funny. I couldn’t believe I was dating a guy who could get any girl he wished. He was the life of the party-kinda guy in every situation.
With stars in my eyes, I never knew until much later that he secretly had several other flings at the same time that he was with me. He made sure I never found out. Slowly I began noticing that things that were off about him, like blatant lies and immediate cover-ups. I didn’t quite know what it was but I suspected the worst. When I finally realized and confirmed that he was, in fact, cheating, I was ready to move on immediately.
#85 Set for Life
One of the moments that made me realize my first boyfriend was a dud was when I asked him why he never looked around before crossing the street. He said he was hoping he would get hit by a car someday, so he could just sue the driver and be set for life. I asked how he planned to do that with his body mangled. He said he was sure he could manage to roll over and look at the license plate.
Real winner, that one.
#86 Daily Routine
Every night, my boyfriend would come home drunk, demand physical attention, and go to sleep until work the next morning. I cannot say that there were no good days in the relationship. There were some better days than others. But things overall were miserable and unhealthy. He would hit me, use cuss words, and throw my things away. He even once asked me to leave in the middle of the night.
The moment I decided to leave the relationship was when it hit me that this daily cycle would probably never change.
#87 Come Out, Come Out, Wherever You Are!
I took a trip to my boyfriend’s hometown, hoping it would be a nice surprise that he would appreciate. The guy refused to come out of his room even though I was standing right outside his place and I knew he was inside. I was calling him continuously. Finally, he picked up and said he was not going to hang out with me. I could not stop crying. I kept asking him why. He said “It’s not you, it’s me” and would not elaborate any more.
Throughout the night, I kept on calling him for an explanation. He would not pick up. I was in a hotel right next to his residence. That whole night, he neither took my calls nor even asked if I made it back to my hotel safely. So that moment marked the end of our relationship. To this day, I have no idea what happened to cause that. I have had no closure whatsoever.
#88 History Repeats Itself
My moment was when I suddenly realized that I was sick of being treated like garbage, and that it wasn’t ever going to change if I was with this person. I did everything I could to make her happy, but just got treated badly every single time. I remembered the definition of insanity and decided not to keep trying the same thing over and over again and expecting a different result.
#89 Ask Me Anything
My girlfriend trusted me so little that she once started a Reddit thread titled “Who has cheated on their boyfriend or girlfriend??” Was she waiting for me to say “Meeeeeee!” or something? I could never get past that and it ended our relationship. Every time I think about it, it makes me cringe.
#90 It Takes Two to Tango
I was dating someone for eight months. We had many trivial problems, but it was one moment in particular that made me quite literally say “screw this” after all. My boyfriend at the time had gone on a trip to Belgium with his friends. One night, I texted him “I love you!!!” He replied with “I’ll talk to you later.” He completely swerved my affection.
Right, don’t overthink. Don’t overthink. What do I do? Overthink. The next day I asked him about it and he said: “Sorry, I couldn’t say I loved you back because I was crossing the road at the time.”
Wow. What a lame excuse. I left faster than the speed of light, and I never felt so damn good.
#91 In for a Penny, In for a Pound
I went out with a woman for about eight months. She was attractive, extremely smart and pretty funny—qualities I really like in a woman. However, she had one quality that increasingly turned me off: not only was she cheap, but she monitored how much I spent on her and derived how much I cared by how much I spent. This all in spite of the fact that her family was so rich, they owned more than one private jet.
The breaking point was when we went to see a movie one day and I asked her to put two dollars in a meter for me while I parked the car. The next day, I got an angry text from her demanding that I reimburse her for the two dollars. I finally decided enough was enough and that I didn’t want to put up with this any longer.
#92 Strange Bedfellows
The moment I realized it was time to end my relationship was when my phone rang from a number with my girlfriend’s area code, and the voice on the other side said “who do you think you are texting my girlfriend like that?”
Turns out, she had been secretly dating another guy for four months while I thought she was home recovering from heart surgery at her parent’s house. We had been dating for four years.
Both the other dude and I dumped her after a lengthy conversation. He seemed like a cool guy. I’d buy him a beer if I ever saw him.
#93 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?”
“Huh?”
“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!).
94 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.
#95 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…
#96 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.
#97 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.
#98 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.
#99 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.
#100 Sweet Estrangement
She bought me a 20-square-foot cinnamon pretzel for my birthday. Good crazy.
#101 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.
#102 How Dare You Know?
He was super pissed 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.
#103 She’s a Sharp One
Drove from San Diego to Chicago in two days after my fiancé attacked 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 legal 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 arrested a few months after I left in an incident unrelated to the above for felony, 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.
#104 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 lifeless. The cops had no leads and the girl was so creeped out she moved as soon as she could.
#105 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.
#106 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.
#107 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 an addiction.
#108 Director’s Cut
I gave him a Rain Man DVD after him mentioning he loved the movie, and he stabbed it to pieces with scissors because he already owned it.
#109 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 end it. Also tried to get pregnant by not taking her BC pills to trap him into a marriage.
#110 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!
#111 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.
#112 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 cuss me out. Then HIS DAD started calling me and threatening me. Lots of crazy over an ugly fake gold necklace.
#113 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.
#114 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.”
#115 Whack-A-Me
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.
#116 Scarface Is Less Cool IRL
My craziest ex became a pretty big dealer while we were together. He really loved it too. Like this guy grew up watching gangster films and genuinely got off on the idea of the adrenaline rush of being constantly paranoid, avoiding cops, and the bouts of violence. 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 gun in his hand ready to end 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 illicit 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.
#117 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.
#118 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 died, and she never got over my death.
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.
#119 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 suicide threats…”I’m gonna end 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?
#120 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 douche he was until after the relationship ended.
#121 Hardly a Wholesome Breakfast
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.
#122 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.
#123 Diagnosis: Lies
Ex-gf faked cancer to get me back.
#124 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 police 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 police 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.
#125 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.
#126 He Did Say He Can’t Dance
Went dancing with a girl from work; first date with anyone, 25 years old—zero social skills, naturally. Wisely, I let her do all the talking, and we have a decent enough time. She doesn’t even seem to notice my awkwardness, and I start to loosen up and even show a bit of confidence. “Hey, this is sort of fun!” I say to myself.
I explain that I can’t dance, but she goads me into giving it a try—just one slow song. She’ll walk me through it, she says, no big deal. No one’s watching. My blood pressure shoots through the roof, but I’m still on a high, and hardly noticing my hands trembling and my pulse approaching a dangerous rate. We go over to the floor and she puts my hand on her waist and takes my other hand in hers.
Instantly, my breath leaves me and the room fills with pea soup fog. The arteries in my forearms and throat contract painfully and a crushing sensation overtakes me; fade to black. My memory cuts out at that point, but I’m told that I managed to crawl to the corner of the room after hitting the floor.
When I came to, I was completely numb and paralyzed from head to toe, gasping for breath, but getting almost none at all. The crushing feeling intensified and I lost consciousness several more times in the next hour or so as I lay in the corner. Eventually, I regained enough feeling in my legs to pull myself upright, stagger to a stool, and order an orange juice. My scalp and tongue were still numb, but I managed to drink it down and gather my thoughts enough to remember where I was, what day it was, and how I had gotten there. In another hour I was aware enough to risk driving home, which I did as slowly and deliberately as I could with my still-dull reflexes and persisting numbness. I made it back to my room and slept until past noon the next day, still a bit numb and groggy even then.
My date, I found out later, had been profoundly embarrassed by my actions, and left immediately after I fell. She forgave me and never mentioned it to anyone, as far as I know.
#127 Mistaken For A Cat Burglar
Suburban Chicago, age 16 or so, super-cold winter night on a date with the future homecoming queen, a sweetie who was game for anything legal for entertainment. I was feeling super broke driving in my parents’ ancient station-wagon with its not-great heater, and proposed that anything we did on our date, we do with money raised by redeeming bottles and cans we found around town. This was before homeless folk cornered that market.
We must not have raised much, because my next idiotic entertainment was “let’s follow a police car around, just for fun.” We found one and got behind it, not too close, but following. After a few blocks, the squad car took off like lightning, went around the block, and pursued us, lights flashing. It being cold in the car I had [winces] put on a knit cap/ski mask which had holes for my eyes, nose, mouth. I had never been stopped by a cop before, hadn’t had my license long, and thought it might be a courtesy [groans] to go see the officer in his warm car, so I promptly got out of my freezing wagon and approached the cruiser.
Out popped the cop, gun drawn, and I was spreadeagled against one of the cars. I did my best explaining to a not-amused cop, and got out alive; my date prolly wet her panties. Next night, at the “youth center” there was different village cop there and I asked him if he’d heard about a pullover the previous night blah blah blah and he said “Yeah; kid near got ended; shoulda never rushed a cop… and the cops last night were looking for a cat-burglar in that neighborhood.”
#128 She Stole My Heart and My Home Décor
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.
Thanks to our friends at Factinate.com for sharing this article with us!
Shutterstock
