These Relationships Crashed And Burned

August 23, 2021 | Scott Mazza

These Relationships Crashed And Burned

Everybody has a story about their worst date, their most nightmarish relationship, or the most awkward wedding they've ever been to. Because for all the talk of "soul mates," it sure is hard to avoid completely deranged "love" stories. These Redditors went into romance with the best of intentions, but all they came out with was disappointment—or worse.

1. Careful What You Wish For

I had been dating this guy for a while and thought things were going pretty well. He took me to see Aladdin, and when we got back to my place, everything was normal. We were conversing, and suddenly he got this weird look in his eyes.

He said, “I can't see you anymore. I'm afraid I might hurt you”.  I was thinking hurt me psychologically, like cheat on me. I laughed and told him not to worry; I was a grown-up, and whatever happened, we could try and work it out. His voice changed, he looked even worse.

He went on, “You don't understand. I've been having these dreams where I hurt you. I mean really hurt you”. Then, he jumped off the couch and ran out the front door. I never saw him again and never tried to call him because it shook me up. He seemed so normal up to that point.

My Date Turned Out To Be PsychoFlickr, David Zellaby

2. He Was A Hippie Freak

I was dating a guy for a month who was a slightly eccentric hippie with a kind heart and a love for spontaneity and bike trips. Then, one day when in the shower, he dropped a bombshell on me.

He casually mentioned he had two kids, was 14 years older than me—not five—and his kids’ mom had a restraining order against him. He ended up pouring patchouli oil all over my door, leaving cursed voodoo eggs on my porch, and sabotaging my bike, so when I went down a steep hill, the brakes fell off, and the bike crumbled.

My Date Turned Out To Be PsychoFlickr, Dave Bezaire

3. Her Fate Was Sealed With A Fish

I took my date and her four-year-old boy to a carnival, and the kid won a pair of goldfish. They were in a clear plastic bag like pet stores use. The boy was very excited. On the way to the car, without saying a word, she did the unthinkable.

She slammed the bag on the pavement, bursting it, and then stomped on the flopping fish. The boy was instantly distraught. When I asked her why she did it, she replied, “They probably would have died anyway”. Then, she called a few weeks later to ask why I had not called her.

My Date Turned Out To Be PsychoPexels


4. My Crazy Ex-Boyfriend

To start our date, this guy and I first went for a walk. He did not shut up for an entire hour, complaining about everything and everyone in his life. He didn’t even ask me anything about my life. We eventually got to a restaurant, sat down, and he ordered food for me without asking what I wanted. Also, when he got his drink, the bartender mentioned the caps are difficult to open, but he arrogantly and rudely brushed him off.

He tried to open it himself but ended up spilling juice all over himself.  He then yelled like it was the staff's fault. He literally had no regard for anyone, just yelling. At that point, I wanted to get under the table because I was so embarrassed. He continued to talk about how superior he was, saying that when he became manager, he would fire people like the bartender.

At the end of the date, I offered to split the check because he mentioned he had money issues. I obviously did not want to see him ever again, so I did not want to feel like I owed him anything. His reaction made my blood boil. He yelled at me, causing a scene in front of several diners. I left the money on the table and walked off.

He continued to yell at me for going after the check.  He grabbed my hand and angrily told me to wait for him. When I said I would just grab a taxi home, he forcefully insisted on walking me home. To avoid him making another scene, I accepted. We walked in silence, so I tried to break off from him and leave, but he insisted on following me home because he thought there might be some dangerous people around.

I was already creeped out at that point, but when we got to my front gate, his horrendous actions solidified my fears. He tried to force himself on me. I said, “I don't think this will work". His exact words were, "You owe it to me. We went on a date, and I did not waste my money for nothing".

When I pushed him away from me, he threw a $20 bill at my face, then said, "Here, we are done!" I instantly got into the yard and locked the fence. I could still hear him yelling, so I sent him a text saying I would call the authorities if he did not get out of there. He finally left. The worst part was his aunt was our neighbor, and my mom knew his mom.

The next day, on my way out, she literally had the audacity to ask how it went. I just told her, "You should have raised him better". They never spoke to me again. I was absolutely fine with that.

Dealbreaker DatesShutterstock

5. I Gave Him My Notice

My boyfriend and I had decided to move in together, so I gave my notice to my landlord. I lived in a college town, so my landlord called the next person on the waiting list, and they signed a lease that day. My now ex-boyfriend was living in a rented room and hadn’t yet given his landlord his notice. When I saw him that night, he said he would have to call his landlord in the morning because it was the last day he could give notice without having to pay rent for the coming month.

We needed his portion of the rent, along with mine, to afford the new apartment. We got into an argument that night, and I decided to go home to cool off. The next day he was unreachable. It didn’t bother me too much, as I had a full day. I called him the next day, and he sounded fine. Then he waited almost a week—and then told me something that made my heart stop. He offhandedly mentioned that he didn’t call the landlord, so he couldn’t move in with me.

He knew I didn’t have the money to move into the new apartment on my own. I asked him why he didn’t call and give his notice that day, and he said it was because I didn’t seem too worried about it when I argued with him that night. I broke up with him right then and there. The funniest part was that he was SHOCKED. Two weeks later, I was living on the other side of the state and ignoring his letters.

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6. Banging Her Head Against A Wall

One night after a fight, I was lying in bed, and my girlfriend fell out of the bed. Maybe she rolled out, but it seemed like a fall. She then stood up and started running into the walls. I just stared in horror. She bloodied herself up real good, and I couldn't get her to stop. The downstairs neighbor heard the commotion and called the authorities.

Officers showed up and saw her sitting on the couch, all bloody. As a result, they became very interested in me. I tried to explain to them she was running into the walls herself, but they didn’t believe me—who in their right mind would?

Fortunately for me, she stood up and ran across the room, right into a wall, practically knocking herself out. The officers ushered us to the hospital. After the hospital staff took her into the back by herself—to ask her if I was hurting her, I'm sure—they allowed me in the back room.

While waiting, she got out of bed, grabbed a bunch of gauze from the cabinet, and started wiping the floor with it. I asked her what she was doing...Her answer was wild. She told me that she was cleaning the floor so the fish could see out of it.

My Date Turned Out To Be PsychoPexels

7. Chivalry Doesn't Exist

I drove my date and I to the restaurant. When I started to parallel park, he said, “I’ll park this for you; women don’t do well at parallel parking". At dinner, he was dismissive toward all the female wait staff. Then, I ran into these two hilariously surfer dudes on my way from the bathroom and they told me my date was a jerk. All red flags. We laughed about it and I went back to my table.

When we were leaving, the surfer dudes were also outside. I said bye to them and my date had the most uncalled-for reaction. He had the nerve to bark, “She’s with me!” I told him to wait for me to get in the car so I could unlock the doors, except I didn’t. I drove off and left him standing there. The two dudes whooped and yelled, “Go, lady, go!” It was such an awesome finish to a terribly embarrassing date.

Petty Revenges factsShutterstock

8. I...Sort Of...Do

It was my friend's wedding. The bride told me two days before that she found her fiancé annoying and that she didn’t like him and that he was AWFUL in bed. She was visibly, endlessly uncomfortable at the rehearsal wedding/dinner combo—and then it got worse. On the day-of, she sobbed the entire morning. She ended up not getting any makeup done cause she wouldn’t stop scream-sobbing.

She refused to get dressed, stalling the wedding for about 35 minutes. At the ceremony, she said 45 minutes of “vows” that she had prepared. It was nine pages of inappropriate vows to friends and family, his parents and sisters, none of them for her husband. She then almost didn’t say, “I do". She managed to get a, “Uh, yeah, okay, yeah I do,” out of her almost a full 60 seconds after she was supposed to say anything.

I could go on for hours, but it was the most painful and awkward wedding I’ve ever been to. I’ve got my money on 10 months. We’re one month in.

Marriages won't lastUnsplash

9. I Was Running With A Devil

I worked with my ex, as we were both correctional officers. I thought that because of our line of work and the background checks necessary, he was a safe bet. I was so wrong.

I was with him for a few months before I moved in with him. After becoming pregnant about a year into our relationship, he started to become a different person.

One day, my oldest son from my prior marriage said, "Momma, I see the devil in his eyes". We had been noticing his personality change; he started saying things to us that made us fearful of his mental stability. The very first sign I saw was his ability to switch between personalities to suit his situation.

Then, as I was moving things to make room for the baby, I found a box of books about "verbal judo". I had never heard of such a thing in my life, but a lightbulb finally went off in my head. Once I began to figure things out, he began to threaten what he'd do if I ever left.

He told me about the slug he had with his name on it and would show it or leave it lying around so that we would see it. He hung up a noose on the back deck that just swung in the wind for weeks. I got my boys and myself out of there. Then came the nightmare. His buddies from the sheriff's office began to follow me everywhere whenever I left the house.

I had never been in trouble, never even had a speeding ticket until this. One time when I went to Walmart, he had a security friend who worked there accuse me of taking stuff. Eventually, the charges were dropped, but he still got me, and I had to fight for custody of my son.

My Date Turned Out To Be PsychoPexels

10. Believe It, We’re Done

I was dating a guy who wanted me to text him my work schedule and then would call me on my work phone and wait in the parking lot for me to come out of work. But that wasn't the worst part. He also wanted to know how much was in each paycheck. One time, I texted him my work schedule, but he misread it and freaked out non-stop for six hours searching for me.

He called my whole family and was about to alert the authorities. It was his own fault he misread what I had texted him. I broke up with him in public because he would not believe it when I broke up with him in private. It was at the point where random people who were nearby were telling him, "you just got dumped".

My Date Turned Out To Be PsychoPexels

11. Tangled In A Web Of Lies

It was June 2018 when the Spider-Man: Into The Spider-Verse trailer came out. I talked to my girlfriend about it and we agreed to go see it when it came out on December 14th. Well, in the proceeding months, we started to drift apart. She was calling and texting me less often, and our intimacy went down the drain. In hindsight, that should have been my biggest clue.

Late November rolled around and I saw on her Snapchat story that she was at a Walmart. She was wearing a leather jacket that was clearly a men's jacket since it was literally two sizes too big for her. For reference, I wore a size medium and this jacket looked like a large or extra-large. Ignoring another red flag, the 14th of December rolled around and I was excited to see the movie.

I had just been fired from my job so I needed a distraction. Her response struck me like a dagger to the heart. She responded that she had already seen it. Cue my confusion and questions about who she went with and why I wasn’t invited. She said she went with a friend from work and didn’t think about inviting me. I knew at that moment she was cheating but I didn’t want to believe it.

A week or so later, my best friend got back from air force school in Texas and we went out for dinner. I texted her to see if she wanted to join us but her response started with, “You’re going to hate me…” and I knew it was a breakup text. I stayed out with my friend and met up with her three days later for the closure conversation.

Cheaters ExposedShutterstock

12. Reverse Psychology

My girlfriend was texting someone a lot when she was at my place one day. She told me she had made a new friend at a party over the past weekend. It didn’t seem like a friendship, but I didn’t push the conversation. The next day, she told me we should break up, and even though I was surprised, I didn’t argue. Then, a week later she tried to get back together.

She sent me a text message saying she missed me, but I told her I'd only take her back if she could honestly confirm my suspicions. She admitted that his name was Andrew and that things ultimately didn't work out between them. Reading that gave me closure, and I was ready to get my sweet revenge on her. So I texted back, "I guess we're both liars now" and blocked her phone number.

Cheaters ExposedShutterstock

13. Honeymoon For Three?

This was my sister's best friend, and it was at her bachelorette party. The bride had been having an affair and everyone knew it. The groom's friends tried to tell him, but she convinced him they were making it up. I mean, at that point it was just sad. She actually had the balls to force her fiancé to apologize to the guy she was sleeping with for the accusations.

The night of the bachelorette party, she actually took all her bridesmaids back to the other guy’s house and spent the night with him. He also came to their wedding. It was so awkward. Everyone knew and everyone was talking. The groom was told, but chose to overlook it. After the wedding the bride insisted the other guy come on a group vacation with her and her husband and included him in all their social functions.

Now, if they're non-monogamous, whatever, go crazy! But her husband was an absolute wreck about it for years and she just kept gaslighting him. No one could convince him to leave her. She told my sister that the affair guy insisted he would never marry her and didn't want kids so she was using her fiancé to get them. They ended up divorcing two years later after their second child was born.

She immediately moved in with the affair guy, and they did end up getting married. The bride and the affair guy are still married and the second child is likely actually his. The groom ended up marrying a girl they went to high school with and seems content.

Marriages won't lastUnsplash

14. Bathroom Break

I'd been totally infatuated with my co-worker for months, so when she finally agreed to let me take her out, I was ecstatic. Little did I know that it would only take 30 seconds for me to lose all interest in her. At some point during our date, we walked down a back alley by the bar and she said she needed to go #1—but what she actually ended up doing shook me to my core.

She pulled her jeans down, TOOK A #2 behind a bin, then searched through the bin for a sheet of newspaper to wipe herself with. I stopped talking to her immediately after that.

Scariest ExperiencesShutterstock

15. Ghosted At The Chapel

I'm a wedding photographer, and these nuptials were a doozy. I sat down with the bride and groom and filled out the contract and then I got the deposit. The groom suddenly stood up, said forget it, and walked out. But I didn’t find out the dark truth until later. Two months later, to be precise. That’s when I get told the wedding is off. Three months after that, the same bride called to rebook with—get this—a different groom—but the story doesn’t end there.

The day of the wedding, I’m at the church. I’d gotten the final payment the week before. So, I’m waiting there one shows. No one. Well, except for me and the DJ.

Marriages won't lastUnsplash

16. Driveway Deception

I found out my boyfriend betrayed me because he didn’t come home after a night out with the boys. I woke up at 4 am and panicked, thinking something horrible happened. I tried to call him but his phone went straight to voicemail, and his friends told me he had left hours ago. I called hospitals and stations thinking the worst. I even called his parents.

They lived in North Carolina and I woke them up to say their son was missing. I decided to drive around to where the boy’s night had been. One of my friends worked at one of the locations they went to and her car was still outside. My gut told me to drive by her house and I was horrified at what I saw—there his car was, still in her driveway. I furiously banged on the door and he answered.

I went home and called his parents back to let them know he wasn't hurt just cheating on me. We had been together for five years and I felt blindsided. The “friend” he was with had been telling me about this new guy who was texting her and sending her flowers. I had no idea it was my boyfriend the whole time. I cut them both off and never looked back.

Cheaters ExposedShutterstock

17. Wedding Night Horror

This newlywed couple I knew were both virgins and were waiting for marriage, in accordance with their culture. Apparently, the groom spent all that time on the internet watching adult films. This, unfortunately, led him to having wild and unreal expectations for his wedding night. He thought it was going to be so kinky.

The shy, religious bride, on the other hand, expected that their wedding night would be a sacred and beautiful coming together of souls, but the groom did not read the memo. He apparently slapped her around, tried to use the backdoor (if you catch my drift) and asked if he could give her a golden shower—all on their wedding night.

The bride was, obviously, absolutely horrified and kept making excuses not to be intimate with him again. He said he had a wonderful time, and kept asking when they could have round two.

Marriages won't lastShutterstock

18. Cheque Please

We had been dating for eight months. One night, while we were out to dinner, she got a phone call. Apparently, her fiancé had just been in a terrible motorcycle accident and he hadn’t survived the ambulance journey. This was devastating news and when she told me, I was shocked. At the time, I was in college, so my schedule was chaotic and I guess that gave her gave free time to be sneaky with another guy. After her confession, I got the bill, made sure she called an Uber, and never spoke to her again.

Cheaters ExposedShutterstock

19. Bachelor Party Proposal

My ex got married to a woman two years ago from a super-conservative religious family. We were still friends for the most part and I was surprised he asked me to be a groomsman but I figured, hey, it's always good to be able to stay friends with your exes—that feels like mature growth and closure. He got really plastered at the bachelor party and at one point asked me if I ever had any regrets about us breaking up.

I said I had loved him but no—we had made the right decision in the long run. And then he told me that he sometimes wishes that we were getting married the next week and how his fiancé’s family will never accept him. Then it got even more uncomfortable. After an awkward pause, he said, "What if we just run away together?" I laughed it off as a joke and said we should rejoin the group.

Then he said it again later again in a joking tone. And then a third time later in the night. We had been friends for years but only dated for like six months. Turns out he asked the same thing to another one of his exes who wasn't a groomsman, but was attending the wedding. The couple is still together technically, but separated.

Marriages won't lastShutterstock

20. Not In The Stars

Our first date was at a Japanese restaurant. She asked me for my star sign and I replied, "Scorpio". She then leaned over the table and she totally caught me off-guard with her next move—she slapped me clean and hard, right across the face. Naturally, I was shocked and confused. I mouthed "What...?" and she firmly said, "I NEVER date Scorpios".

I went to the bathroom to compose myself, and when I came back, she had gone and paid for everything.

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21. Not The First, Definitely The Last

I thought I was eventually going to marry this guy I was seriously dating and I never saw this coming. It’s still fresh because it happened last weekend. When we first started dating, I remember a pack of protections being in his nightstand. We had gotten tested together and our relationship was supposed to be monogamous, so I forgot about them.

Last weekend, I had a weird feeling. I checked the nightstand and the pack was gone. Something led me to the closet and my jaw dropped when I looked inside. I found the overnight bag he used to bring to my place whenever he stayed the night. I thought to myself, he hasn’t used that in a while. When I opened it, there were dirty clothes, wrappers, and all sorts of intimate goodies placed in individual bags.

My boyfriend told me he didn’t like doing freaky stuff, so when I saw what was inside the bag, I knew he had been unfaithful. This prompted a full search and I found a secret play dresser full of role play costumes, lingeries, and devices that I had to Google! I confronted him about it and he denied it at first, but he eventually admitted the truth. He had no intention of telling me.

Cheaters ExposedShutterstock

22. A Picture Says A Thousand Words

When I started dating my ex, he told me he was divorced. I met his friends and everyone told me the same messy story. One night, we were out dancing and one of his wife’s friends saw us and sent her a picture. She sent it to him while we were still out and I promptly ended things. I will never forget the look on his face after opening that text.

I wanted nothing to do with him and carried on. The best part was when I ran into his wife at the same club a few months later. The encounter completely took me by surprise. She held no anger towards me, and she was actually an amazing woman! Though, she is still married to him. We decided to send a picture of us together, just to make sure he knew how low on the totem pole he sat.

Cheaters ExposedShutterstock

23. A Load Off His Mind

I was at a wedding where the best man got super plastered before he made his speech. Well, that turned out to be a problem as he had a lot on his mind. He said: “We all know how easy the bride is. I can name at least seven guys here she’s been with". But he had another bombshell to drop. He continued and said: “To be fair, it’s not like the groom is much better. Let’s not forget he was with MY wife a few weeks ago".

Well, the speech lasted about another five minutes. He got even more sloshed at the wedding and couldn’t stand by the end of the night without help. As for the marriage, it lasted just over 18 very rocky months—the last few months were the worst. Technically they are still together, it’s a long story. They don’t live together anymore and the divorce was filed a long time ago and he is just making it as hard as possible.

Marriages won't lastShutterstock

24. A Christmas Gaslight

I decided I would tell my partner I wanted to break up while I was at my parents' house for Christmas. At that point in our relationship, he was a workaholic and super distant. For the past two years, it felt like nothing I said or did even mattered to him. I tried to talk about how unhappy I was but it just didn’t phase him.

The last conversation I tried to have with him involved him interrupting me with a giggle fit because he "started thinking about how funny and cute a basket full of kittens would be". I didn’t think he would even blink reading my message about separation but he actually told me he'd like for us to work on our relationship.

He hadn’t booked off anytime for Christmas so I was alone. I felt terrible that I had left my parents. When I was opening presents with them on FaceTime, his iPad notifications were going off loudly in the background. I went to turn down the volume and I was shocked to see the messages on the screen. They were all from one of his old co-workers and something felt off.

I opened up their chat and read the whole thing. Turns out, he'd been planning to cheat for months while I was away. Besides her, there were two other co-workers he was talking to flirtatiously, one of which had children closer to his age. I confronted him and he lied. He also tried to erase his text messages on his phone, not realizing that they don't get erased on the iPad regardless.

Cheaters ExposedShutterstock

25. Not A Gentleman

This guy and I were eating dinner after chatting for a couple of weeks. Out of nowhere, he said something completely unrelated to what we were discussing, and it had me fuming. “So, you order for this to work, you’re going to have to share yourself, right? My friends and I like to pass girls around".  I was dumbfounded.

After a bit of stuttering, I told him I didn’t think it was going to work. I asked for a to-go box and my portion of the check.

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26. We’ve Got The Receipts

I had suspicions for a long time that my husband was cheating, but every time I accused him, he managed to spin it and make me feel paranoid. Looking back, there were tons of red flags; but the way I found out was through digital intervention. One night, at work, my phone rang and I didn’t answer because it was an unknown number.

Immediately after, my husband called, sounding frantic. He screamed at me, “You’re about to get a phone call, don’t answer it!! It’s all lies!” I was intrigued and I asked him to explain. He continued, “Melissa’s boyfriend thinks we’ve been sleeping together and he’s on a paranoia rampage". I called back Melissa’s boyfriend and he said three words that turned my life upside-down: "There are pictures".

They weren’t just pictures, either—he also had screenshots and wanted to send them to me. I declined the proof because I had known all along. I believed him, thanked him, and called my husband back. I told him he had the night to pack and better not be home when I got off in the morning. The relief was overwhelming and I never doubted my instincts again.

Cheaters ExposedShutterstock

27. Dodged A Bullet

This happened when I met someone from an online dating app. He turned up with pupils the size of dinner plates and he was super erratic. He said he'd forgotten his wallet, so I got the first round. We were on the way to the second pub to meet his mates so they could lend him some money. During the walk there, he spoke absolute nonsense non-stop.

I was still open to giving him a chance, but then he told me a story that chilled me to the bone. He basically told me, in graphic detail, how he drowned his ex's chihuahua in a pool.  I knew I had to get out of there ASAP. Near the pub, he got a call and said he needed to answer it. At that point, we were 30 minutes into the date and already going to the next pub.

He had downed his drink in about three seconds, whilst he stood there on the phone. That's when I told him I'd meet him at the pub since it was in close proximity. Instead, I walked right past it and ran all the way home.

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28. Ex Marked His Spot

I was at a wedding where I was a plus one for my date. The bride was totally inebriated and sat down at our table and started talking to us. She then told me that she’d slept with her ex right before walking down the aisle. She literally did it with her ex in her wedding dress in the bridal suite. She then downed the last of my drink and went off to the dance floor.

I was left speechless. Less than a year later, the bride and groom were divorced.

Marriages won't lastUnsplash

29. Everything You Say Will Be Used Against You

I showed up to bail my boyfriend out. I had no idea why he was locked up, but as I was signing bail forms, I overheard the conversation behind me. The bondsman was talking to a woman, and he asked her how she knew my boyfriend. Her response startled me. Without any hesitation, she said they were dating. I slowly turned around, thinking I must have misheard.

I asked her who she was and she recognized me. She said it was nice to meet me, which was surprising as I didn’t know who she was. I found out my boyfriend had an ongoing relationship with another woman, but that's not even the worst part—it turns out that she is 20 years my junior. The night before, she had put a restraining order on him, which he violated the next morning, hence the arrest.

Cheaters ExposedShutterstock

30. Made For TV

I went out with a girl for a first date. She took me to a Kumdo lesson, which is a Korean sword fighting sport. I thought that was cool, but it was an advanced class and I made somewhat of a fool of myself. Still, I had a lot of fun...until I uncovered her shady ulterior motive. Turns out, she brought me there not because she wanted to go on a date, but because she wanted me to be part of a documentary about foreigners in Korea.

I was shocked, but I had no choice but to just roll with the punches since I was already deep in it. We then visited her grandmaster's house for makgeolli, and the film crew started interviewing me. They kept asking us relationship questions as if we had been going out for years. They didn't seem to understand it was the first date.

So there I was, trying to answer awkward questions without embarrassing both of us on national television.

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31. The Den

Before I went on a date with this new guy, he  invited me into his apartment while he finished getting ready. No biggie. Once inside, he insisted that I see his "dungeon". The unit itself was pretty empty, minus a TV and couch, but his bedroom was fully kitted out. I was already creeped out, but then he took it one step further. I was appalled by what he asked me to do next.

He asked me to see if the shackles on his bed fit me. Thankfully, I had set up for a friend to call me within the first 30 minutes of the date and I faked an emergency.

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32. Six Degrees Of Relationships

My boyfriend and I broke up and I started meeting new people. One of the new friends I made asked if I was seeing anyone. I told her I was newly single and mentioned my ex. Her face turned white when I told her his name. She was surprised because she had also recently broken up with someone by that name. We took out pictures and it turned out that we had been dating the same unique twit.

Cheaters ExposedShutterstock

33. This Wedding Was No Cakewalk

This happened at the reception of a wedding I went to. The cake had come out and the bride was trying to playfully feed the groom a piece of it. She kept pulling it back once it got close to his mouth. The third time she did this, his reaction was chilling. He slapped it out of her hand and stormed off. In the ensuing awkward silence and wide-eyed staring, we all knew it wouldn't last.

Surprisingly, they were together for nearly two years—but the biggest surprise was yet to come. The bride ran away with her stepbrother and eloped. No one saw that coming.

Marriages won't lastUnsplash

34. Not A Family Guy

This guy I was dating invited me and a friend to play dodgeball with a group of folks I had never met. We were having an okay time—he was paying more attention to his friends, but that was fine because I had my own friend to keep me occupied. We were hanging out in the parking lot before the first game was about to start when, out of nowhere, he grabbed a ball and threw it at my crotch as hard as he could. He then screamed: “Wham, bam, right in the clam!”

I immediately turned to my friend and asked her if she was ready to leave. I said goodbye to him at that point. When I got home, I checked my phone and it had been blown up by multiple texts about how “immature” I was behaving.

Cheaters ExposedShutterstock

35. And You Say He’s Just A Friend

I had been dating my girlfriend for eight months. On her birthday, flowers arrived from a guy named Matt. She managed to convince me that he was just a friend. I was meeting her family for the first time that night, and she told me it wouldn't make sense for her to invite me if she was seeing someone else. In my mind, we were on track—we had even exchanged the L-word for the first time a few days prior.

After dinner, I stayed at her house, then left for work in the morning. Later that day, she wasn’t answering my texts. I tried asking what we were doing that weekend, and that’s when the dark truth came out. Matt was her boyfriend of five years, and she was moving to be with him in the house that he had bought. She was leaving that week and didn’t think we should stay friends. That left me with just a few trust issues.

Cheaters ExposedShutterstock

36. Picture Imperfect

This is what happened at my brother’s wedding. Throughout the exchange of vows, the bride was looking at everyone—except my brother. She was busy making sure all eyes were on her. Later, she instructed the photographer—a family friend who was cheap—to “mingle” and get shots of people “being happy”. Within 10 minutes, she’d summoned the photographer back, shouting, “Whose wedding is this?! I meant get shots of people being happy for me".

They broke up when she cheated on him. Apparently, the marriage that she was desperate for was only good while it brought her attention.

Marriages won't lastPexels

37. One Thing After Another

I went to a bar and met up with this cute girl. We got along pretty well. She invited me back to her place, but she eventually met up with friends at the bar. Near the end of the night, they were all tipsy, but her friend was insisting on driving home because she was very set on not leaving her truck parked outside a bar overnight.

So, I offered to drive her truck home. We got all the way to their apartment complex but getting into the parking spot was tricky. The friend who owned the truck then insisted on parking it for me. She essentially pulled the "I legally own this vehicle" card on me. Since I was just some guy her friend just met at a bar, and it was technically her truck, I was like, "...Okay then".

Within five seconds, she immediately regretted her decision. She backed the truck into a drainage ditch and got it stuck. We all had to push the truck and we got covered in mud. While we were doing that, the girl I met at the bar had lost her wallet, so I dug through the mud and water-filled ditch to find it. We got back to her place and the mood was definitely ruined, so we ended up eating a random cheese and meat platter from Safeway on her kitchen floor at like 4 am.

I slept on the couch, then woke up early the next morning and I thought to myself, "Well, she was great; it was just the whole truck thing that ruined it". I looked for a pen and paper to write down my number before leaving, but all I could find was a piece of paper taped to the inside of the door. It was a court date notice for a domestic case hearing. I just left and chalked it up as a strange night.

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38. Sister In Your Corner

My partner was visiting his family across the country when his sister called to tell me that his ex-wife had driven up there and they were back together. I had never met his sister, so I knew it was serious. I asked to speak to him. He promised me his sister was just jealous of his happiness but I couldn’t ignore it and I broke things off.

After a few months passed, he called me and said he wanted to rekindle our romance. I wasn’t overly eager but his sister swooped in again with a bombshell reveal. She called to let me know after our break-up, he had remarried his ex-wife. This time, he didn’t deny it; but he was persistent that we should be together even though he was married. I blocked the number and thank the sister every day.

Revenge neighborsPexels

39. Oedipus Wrecks This Wedding

We noticed during this wedding that the soon-to-be mother-in-law of the bride was insufferable. Every chance she could she would make it about her and her son, the groom. God forbid she let her new daughter-in-law have the spotlight. The mother-in-law had the photographer follow her around for most of the wedding. Most pictures have her in them.

She was always near or around her son, but like always touching him too. It was weird. We joked that all three of them are going on honeymoon together. She gave an hour-long toast about how she is still the most important person in her son’s life. I think she said something like, “You may be his wife, but he’ll always be mommy’s little boy". She always went into way too much detail about how she breastfed and changed his diapers.

She danced with her son more than the bride. And I’m not talking 60/40. Like 90% of the time it was mother and son dancing. At one point she was even bumping and grinding on him. So at no point did my girlfriend and I think the bride was going to put up with this crazy mother-in-law for more than a couple years. Sure enough, she got pregnant soon after the wedding.

A couple of months after the baby was born, she filed for divorce.

Marriages won't lastShutterstock

40. Falling Down The Family Tree

I was in a long-term and long-distance relationship with a girl who I truly adored. We saw each other as often as we could and always made the most of our time together. One weekend, she traveled with her mom to visit her grandmother and reconnected with a male cousin. They hadn’t seen each other since they were children.

The next time she came to visit me, she planned a detour on her way home to stay with her grandmother and cousin for a few days. She spoke about her cousin a lot and I was genuinely pleased that they had reconnected. When the weekend ended, I walked her to the train station, kissed her goodbye, and wished her a lovely stay with her grandmother.

A couple of days passed and I didn’t hear anything from her, which was unusual. I called her mobile phone a few times and sent her text messages asking if she was OK, but got no reply. On the fourth day, I called her mom to see if she’d heard from her daughter. She had, so I couldn’t understand why she hadn’t called me. Her mom gave me the grandmother’s number.

I called and her grandmother answered. I asked to speak with my girlfriend who came straight to the phone, unaware that I’d been given the number. When she heard my voice, she went very quiet. Then, she revealed the shocking truth. I eventually got her to admit that she “had feelings” for someone else. I naively questioned it because she’d only spent time with her cousin...Bingo.

Cheaters ExposedShutterstock

41. Honeymoon For One Please

A friend of mine was getting married and she was planning her honeymoon. She’d always dreamed of sitting on a beach on a Caribbean island and she wanted that for her honeymoon. The only problem was that her fiancé had a severe sun allergy. My friend went ahead and booked the honeymoon anyway, even though I thought it was a terrible idea.

About the groom’s sun allergy: it was really serious. He had red hair, really fair skin, and burned up within minutes. And I mean really bad sunburn, the kind you have to go to the hospital for. He always had to wear sunglasses, long-sleeved shirts, and a hat, even on cloudy days, so the vacation was definitely not for him.

When she went to tell her groom, I expected him to be livid. His reaction knocked me off my feet. He actually suggested that she go alone—on their honeymoon! These two married young and it didn't occur to them that it would be strange if she went on the honeymoon and he stayed behind. He was a good guy and just wanted to see her happy, and she really wanted to go on this vacation, because she had never left the country.

They separated half a year after the wedding and my friend, the bride, told me that the marriage had been a way to prolong the relationship despite both of them knowing that it was already over some time before they got married. Kinda like a couple gets a baby to save a marriage. It really was just sad because they were a nice couple, but they stayed friends after separating.

And I can guarantee that she didn't cheat on him while away, they were both really loyal.

Marriages won't lastPexels

42. I Spy

This guy and I were having great chats online, so we decided to meet in person. He showed up wearing a Bluetooth headset with a little LED light that indicated it was on. He kept it on during drinks. I worked up the nerve to ask if he could take off the headset while we were eating dinner. With pride and complete confidence, he gave a response that sent shivers up my spine. "Don't worry! You totally have my full attention. This isn't a phone headset, it's a camera".

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43. Shocked Into Silence

My boyfriend at the time didn’t think twice about wrapping his arm around one of my friends and then kissing her. She wasn’t my best friend, but we were still pretty close. I had to walk away to process it, and I don’t think they even noticed. The girl came to find me later and I immediately wanted to know what was going on. I thought I already knew the whole story, but when she explained it, I was thrown completely off-guard.

Apparently, everyone in our friend circle knew they were also dating and assumed I also knew. They had been seeing each other almost the same length of time we had been dating. I felt like I had to accept it because no one else thought it was weird. The whole experience gave me a good lesson on boundaries and self-worth.

Cheaters ExposedShutterstock

44. Friends With (Medical) Benefits

This was at a friend's wedding back in 2016. It turns out that they were getting married quickly because the bride, my friend, suddenly needed medical benefits—which he had through his job. This was not a great reason to get married and it didn’t bode well for the upcoming marriage. That said, there was no excuse for the terrible behavior we saw at the wedding.

I was a bridesmaid and really hadn't met the groom much prior. All I can tell you is that he was nice, but quiet. The day before the wedding the bride asked me to help babysit one of the groomsmen because he was a nightmare. She didn’t just ask me. She also asked another bridesmaid, the DJ, and others to help watch the nightmare groomsman.

Our job, she instructed us, was to cut this groomsman off from booze before the ceremony, not to allow him to make a speech, to keep him from hitting on girls, the works. This guy was an alcoholic jerkbag that had managed to have six kids and two DUIs. Somehow he was the absolute best friend of the shy and quiet groom.

The day of the wedding, the best maniac breaks into the bar, gets hammered, and has to be dragged down the aisle. He gets the florist smashed, while they pretty much do “it” on the dancefloor. He makes, what I can only assume to be, a speech during the father/daughter dance. The bride was super angry and stressed, as well trying to get things to not be a total mess.

The groom blocked us from keeping the groomsman in check, and wanted us to just let it go while he did everything the bride asked him not to do. It was like a weird purposeful or intentional self-sabotage thing. The groomsman also broke into the groom's private stash of homemade mead he'd made special just for the wedding.

He also stripped his clothes, and ran through the parking lot, and hid in bushes at 11 pm. So the groomsman was a write-off, but then the groom took over being the wedding’s most deranged participant. After the wedding was finished, I got a text from the groom. He asked me if I wanted to have a threesome with him, and my friend—otherwise known as the bride.

It turns out that this was the bargaining chip for his medical benefits. If she wanted the benefits, she had to open up the relationship. The divorce was finalized a year and a half later.

Marriages won't lastUnsplash

45. If You Invite Two Friends

Back in high school, there was a very beautiful girl named Melissa in a few of my classes. This was in the late nineties, and pregnant teenagers weren't as common as they are now, so I think it added to her mystique that she had a child. It never bothered me, though. I just thought she was the most beautiful woman I had ever seen. So, any chance I got to be around her, I took it.

She needed a tutor? Check. Someone to talk to? Check. I never had the guts to ask her out, though. I wasn't much of a looker myself in high school, so it took me a pretty darn long time to do it. Finally, I did, and she said yes! I can't remember how it went down, but I think we decided that I'd pick the restaurant and she'd pick something else to do.

It was all great until she showed up on our date with a totally unexpected surprise. She brought her sister along with her. That should have been my cue to just go back inside my house, but I didn't because I was an idiot. We went to eat, and then she said she had a "surprise" for me that she thought I'd really enjoy. I was excited; did she really plan something?

We pulled up to a small convention center and started to head in. I was already starting to wonder what we were doing as we made our way towards one of the rooms, and there it was...clear as day on a sign out front of the door—a pyramid scheme. I cannot describe my internal anguish and feelings of absolute fail during the lecture and the meet-up afterward.

They didn't even sit with me. We'd arrived late, and they moved to open seats on one side while I sat on the other. I barely remember how I answered the inundation of the people's questions, but somehow, I made it through the evening. I remember never even seeing Melissa or her sister during this time, and when we finally met up to go home, I was utterly destroyed.

When we got home, she looked me straight in the eyes and told me that she had a really nice time that night. I echoed the sentiment, told her sister it was nice to meet her, then went inside. I never even looked at Melissa again.

Cheaters ExposedShutterstock

46. Failure To Launch

I was dating a co-worker for under a month, but he was already saying big sentences like, "I think I'm falling in love with you". I responded with, "I need to go slower". I don’t have a lot of relationship experience and I wasn’t sure what was acceptable timing, but it felt too quick. One night, a group of us went out for dinner.

I noticed he was being super affectionate with another colleague. He was whispering in her ear and touching her arm, barely paying me any attention. I decided to end things a few days later, but he said we could go slower. He insisted we had something special and that I should stick it out. I felt conflicted but I ultimately agreed to continue dating.

Two days later, I walked into an unexpected surprise in the breakroom—I found him with the same colleague from dinner playing tonsil tennis. I think I gasped and that caused them to pry their faces apart. My head-over-heels Romeo then said, "Hey, we are going to go out to dinner, you should join us!" I was too stunned to respond...I just turned around and walked out.

Cheaters ExposedShutterstock

47. No Game

He was 45 minutes late picking me up, but the weather was quite poor, so I gave him a pass. When we got to the coffee shop, I took off my jacket, and he immediately uttered a sentence that made me feel super uncomfortable. “I see you brought your A-game, or should I say, D-game,” referring to my breasts. Even the people two tables over just stopped and looked at him.

Horrific Birthday FactsShutterstock

48. Ebony And Ivory—But No Harmony

This was my wife's friend. She's a very conservative, religious white girl who married a black man. Most of her redneck family didn't approve of the marriage and didn't show up to the wedding. But that wasn’t the cringiest part. She planned the whole marriage around race. Like a vanilla cake for her, and a chocolate cake for him. The wedding colors were black and white, and even the meals were white meat for her side and dark meat for his.

It was extremely uncomfortable as a guest. They lasted two years.

Marriages won't lastShutetrstock

49. Slashing Good Time

He brought two friends along, which was unexpected. They were all drinking. I flagged down a waitress while one guy left to go do something. As I ordered my food, my date, and his other friend confessed they'd already eaten. Then the third guy walked back into the restaurant and when I saw him, I gasped. There was blood dripping from a horrific gash in his arm.

In shock, I ran to my car and grabbed my first aid kit, then cleaned and butterflied the wound. I put bandages on his arm and had the guy elevate it while the waitress called an ambulance. I got cleaned up and returned to find the other guys had just eaten my food. I grabbed my kit and my purse and walked out.

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50. Netflix And No Chill

This girl I went on a date with turned out to be just a nasty, rude person. Maybe she had a bad day, who knows; but she said something that just made me lose all patience with her. We went to a cool-but-not-expensive hipster restaurant on a Friday night and they were busy. She complained the whole time about the service being slow, saying that they were stupid for having a hard time understanding her over the loud noise.

She made fun of the other customers, but not in a clever, observational, "Larry David" way. She was just senselessly mean and petty. The breaking point, however, was when she made a shocking comment about my appearance. She probably intended it to be some sort of flirtatious shade, but I took it personally. I wolfed down my food and then signaled for the check.

I waited for an agonizing five to 10 minutes for it to come. I stood up, threw down enough cash for my meal and a generous tip for both of us (she’d been such a monster to the servers that I knew she wasn’t going to tip anything), and I started putting my windbreaker on.

She asked me, “Are you cold?” “No". “Oh. Where are we headed next then?” “Home". When I said that, she looked confused for a second, then gave me a coy look and said, “Oh OK, yeah, I’m down for Netflix". Realizing what she thought I was implying, I just said, “Oh, no, I meant I'm going home...alone". Off the patio, I went right into the street.

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51. Uncontrollable Urge

This guy I went on a date with was a friend of a friend. He went to a restaurant and ordered our food. While we waited, he started to say things like, “First I’ll eat this meal, then I’ll eat you". I laughed because I thought he was just joking. I thought he was just nervous and his mouth lost its filter. Then, when the waitress asked if we wanted more to drink, he was like, “Yes, bring us something strong".

I said not for me since I had to drive later and he looked at me weird, saying, “Don’t be stupid. Do you think I’ll do you once and let you leave? You’ll at least stay the night". The waitress looked at me with wide eyes like I was crazy for even being there. After she left, I told him that he had to stop with this—I said he was being rude and that we were only on our first date.

He apologized and for about 10 minutes it was okay. Then, as if a switch was flipped, he went back to being a monster. “You know what, I can’t control myself anymore. Either we go now or I’ll put you on this table". I told him I had to go to the bathroom. I silently went to the waitress, paid for the food, and left without a word.

Awkward DatesShutterstock

52. Stalker

It seemed to be going alright for a while with this girl. One afternoon, we went for a stroll around town, doing a little bit of a pub crawl with a drink at each place, followed by some food at a monthly food truck festival that I knew about. All this was going to be followed by a local bar and dancing. The entire time, I kept seeing the same guy at all the locations who was obviously following us.

On a toilet break, I mentioned something to one of the pub doormen and he asked the man to leave politely. My date noticed what was happening and she suddenly ran over to the doorman. I was so confused until she spilled the awkward reality—it was her husband. They had a kink of watching each other go out with someone and maybe watching them hook up.

I left them with the doormen and reported them to the authorities.

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53. Objection Overruled

I used to be a Deputy Sheriff and part of my job was taking in-custody defendants to their court dates. One particular defendant happened to have two court dates on the same day. The first court date was, to my surprise, his wedding date. The other case was for roughing up his girlfriend— the same one he was marrying. They were getting married so the bride could not be compelled to testify against the groom.

So when we were at the wedding court date, the judge did the usual thing and asked if there was anyone who objected. The Assistant DA in the back stood up and proceeded to blow my mind. The entire courtroom went completely silent until the Judge spoke, 'Well who am I to stand in the way of love?' And with that he banged his gavel, they were married.

The ADA's case fell apart, and the defendant was released that day. He was, however, back in prison by the next week. I'll let you guess what he was taken in for. So what happened in the end? The good news is: no he did not kill her. The bad news? The last time I saw her she was pregnant with his kid.

Marriages won't lastShutterstock

54. Weird Pal

I was talking to a guy who was a math professor. He invited me on a date to an outdoor play where he was playing an "important role". I showed up to see it was a church picnic and he was playing the devil. He introduced me to his family and all they talked about was Weird Al. Like, they didn't listen to anything BUT Weird Al.

Then, his sister loudly interrogated me about why I went to a private school. Unbeknownst to me, he had told them everything about me and every conversation we ever had. I faked an emergency to get out of there. Later, he asked me out on a second date and he said he wanted to take me to the state fair with his whole family.

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55. Young Love Is A Rollercoaster

My first serious girlfriend after high school worked at an amusement park. I would pick her up after work and we'd hang out because everyone there was pretty cool. We started spending most of our time with another couple and another male employee. One night, it was super late and my girlfriend still hadn't called me to pick her up.

She wasn’t replying to my texts, so I just started driving there thinking we'd all hang out in the park after hours as usual. I decided to swing by for some McDonald’s first and that's when everything changed—I ended up seeing my girlfriend and her coworker splitting a milkshake. It looked like a scene from a romantic movie. I messaged the couple we were friends with and found out that they had been going on dates for quite some time.

Years later, they got married, had a couple of kids, and then got divorced. I haven’t stayed in touch with anyone from the park. My ex did reach out on Facebook a couple of years later to see if I was going to our high school reunion. I ignored the message and skipped the reunion. I couldn’t live in the past and there was no way I was going to repeat high school.

Cheaters ExposedShutterstock

56. Too Casual

He showed up in sweatpants for an evening meal and spent the whole time talking about how he only dated nurses because he's lazy and they are great caregivers. But that's not even the worst part. He also talked about his last girlfriend who, after working her shift, would come over to his place and do his laundry. I was a cook, but he said he was willing to "give me a shot" depending on how good my cooking was.

When we left, there was a busker outside with a crowd and we stopped to watch. I slowly edged my way into the back of the crowd and then quickly walked away.

Hurtful Comments factsShutterstock

57. Tingle And Multi-Mingle

I met her on a dating site and she lived in a different city. We started texting and calling each other on a daily basis before I went to visit her for a weekend. The trip was great and two weeks later, she came to visit me. Everything felt good and we continued dating for a few months. We even took a vacation together and I felt happy.

Then, I began to notice that the things she told me didn't always add up. I gave her the benefit of the doubt, but I had this growing, subliminal suspicion that something was wrong. One night, I ended up with her phone in my hand when she went to the bathroom. I looked at the screen and my heart stopped—an email popped up from a guy named Christian.

Christian was confirming the flight he had booked for them. I opened it and took a picture with my phone, but didn't confront her immediately and took my time to process. I asked her how many boyfriends she currently had and explained my gut feelings. She admitted to dating other people but told me nothing was as serious as what we had.

Then, I told her I knew about Christian and said he deserved to know about me. Immediately, she got emotional, begging me to leave him out of this and saying through tears that they had plans. I ended things that day and wrote an email to Christian that night. He didn’t know she was seeing other partners either and found out she had been dating both of us at the same time.


Cheaters ExposedShutterstock

58. He Gave Marriage A Shot

Before a wedding I was supposed to attend, we all met at the groom's house on our way to the bachelor party. We gathered around for a shot and his toast, verbatim, was, "To my future ex-wife". We all looked at each other awkwardly for a moment, but ultimately didn't think much of it and had a great night. It turns out he was already cheating on her, ended up having a kid with the other woman, and got divorced when she found out. He is obviously no longer a friend.

Marriages won't lastShutterstock

59. The Path To Love

My girlfriend left to go camping for a few weeks. A week and a half into her trip, she posted a Snapchat from Florida with another guy hugging her from behind in a hotel room mirror. Apparently, during this camping trip, their paths crossed and after only knowing each other for a couple of days, she moved there. She told me I couldn’t be mad at divine intervention.

Cheaters ExposedShutterstock

60. Not In Your Future

This girl I went on a date with claimed that she could see angels in three different colors. Apparently, during one of her "encounters," the angel was covered in dark scales, with red glowing lights coming out from her skin underneath. The angel came to her in the middle of the night, crawled to her bed, then placed its hand on her shoulder in order to cast an evil spirit out of her room.

If that wasn't creepy enough, she then said that while I was in the bathroom, an angel came to her and informed her of my chilling fate. She said she knew when I was going to die and how it would happen. I told her I'd be right back, saying that I left something in the bathroom. But I left instead, completely creeped out by her. I still wonder what strange stuff she was getting into.

Abandoned Places FactsShutterstock

61. Great Expectations

We met at the restaurant and I arrived first to get a table. Once she got there, she walked over to me, shook my hand, and I pushed her chair in. Then the server asked us what we would like to order. Ignoring her, she looked intently at me and asked a startling question: "How much money do you make?"  I said, "Excuse me?" in a confused tone, somewhat taken aback.

She stared at me and very slowly asked again, "How much money do you make in a year?" I looked over at the server who was still standing there with a really awkward look on their face and thanked them for their assistance so far. Turned to my "date" and said I was sorry, but I had to leave, and I got up and walked out.

Midsection Of Woman Holding WalletGetty Images

62. Flush Away The Future

My girlfriend had a studio apartment and lived alone. One day, when I got to her place, I went to the bathroom and saw used protection in the trash. We had stopped using protection, so she confessed easily. We still stayed together and she promised me she would change. A year later, she found out I got invited to this exclusive party.

She kept urging me to take her, convincing me it would be fun for both of us—little did I know that she had shady motives. I didn’t realize it, but her ex was also invited, and that's why she made a big deal about me bringing her. I was invited for work and had to organize a plus one so it was a huge hassle. I regret it to this day because I ended up finding her with her ex in the toilets.

Cheaters ExposedShutterstock

63. Three Of A Kind

I met a woman for a mid-afternoon meal. It was a nice day, so we sat outside. She was slightly odd but there were no major red flags...until she hit me with a huge surprise: “Hey, my husband is on the way with our dog. Come meet my dog". I thought, “Well, I wasn’t expecting this,” but by that time, he was already with us. We chatted for a bit, but I didn’t say much to the dog as it was all a bit embarrassing all around.

I paid the bill, made some excuses, and left them to it. He was a nice dude and deserved better.

Rejected Proposals factsShutterstock

64. Expensive Taste

I went on a first date with a girl who insisted we go to a really expensive place. When we got there, she ordered a $25 appetizer, a $45 steak, and a $15 drink. She wouldn't put down her phone and she kept taking calls and answering texts. The waitress noticed and motioned for me from behind her. I excused myself, and the waitress had separate bills all made up.

She then asked if I wanted to pay my share and leave her at the table. I said, "That would be wonderful!" So, I did.

Creepy DatesShutterstock

65. Not A Match

I matched with a woman on Tinder and we hit it off pretty well. She was a “furry” and I am not, but she was pretty, and I was looking for something casual. Eventually, we planned to hang out at her apartment downtown. I got there and her place was incredible—like, she was obviously a wealthy woman and I was blown away by the unit.

We went into her living room and there was a guy there. Roommate? Nope. Friend? Nah. It was her boyfriend. Then, I had a cringe-worthy realization: it turned out this woman was polyamorous and didn't plan on telling me, a big no-no. I sat down and endured her trying to get me and the other guy acquainted, but he was wholly uninterested in speaking to me. No hard feelings though; the feeling was mutual. I dipped out in about an hour. It sucked.

Awkward DatesShutterstock

66. Turn Left And Break-up

She was driving and handed me her phone so I could navigate the directions. While I was holding her phone, she got a message from another guy. I had already told her their friendship made me uncomfortable and she said I had nothing to worry about. But then I read the message and I broke down. He wanted to know what time to pick her up for their date. I calmly asked her how I should respond.

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67. Replacement Dad

I met her through an online dating service. On her profile, she seemed to be a fun, interesting person. When we met, at a Denny’s of all places, it turned out that she had omitted some parts of her background...and boy, did it throw me in for a loop. She was actually about 10 years older than she had initially disclosed, and she was divorced with two kids.

Apparently, she was looking for a new daddy for them and I was one of the options. She also had certain ideas about how much money I needed to be earning. I excused myself and left after paying for the check. That was the biggest nope I had while dating.

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68. Not Ready

I went to pick up a girl for a date in my car on a hot summer day. I had the air conditioning blasted. When I arrived at her house to pick her up, she came out and got in. About five minutes down the road, she proceeded to ask me if I could turn off the A/C because she felt like she was going to get sucked into them. I was kind of weirded out by the comment at first, but was like, "Okay sure". So, I shut them off.

After another five minutes down the road, she pulled a bottle of water out of her bag. She then asked me the most peculiar question ever: "I forgot to brush my teeth, is it okay if I do it in your car?" That's when I told her I didn't think this was going to work. I turned around and dropped her back off at home. That was definitely one of the weirdest 10-minute dates I've ever been on.

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69. Ciao, Bella

My girlfriend at the time didn't have a phone, so she would contact me using her friends' devices. One day, I was trying to get a hold of her, so I texted some of their numbers. After a few minutes, I received a shocking reply, and it hit me like a runaway train:  "You need to stop. She broke up with you and is seeing someone else. Leave her alone". This was far from true. We had not broken up...In fact, we had even scheduled her dream vacation to Italy for her birthday.

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70. Merry Christmas Rusty

The first red flag for this date should’ve been his age—turned out, he’d fibbed about it on his dating profile and he was actually my dad’s age—but I vowed to muddle through. During our pre-date conversations, I’d mentioned I was into F1 racing and he said he’d attended the Canadian Grand Prix. He even brought an ancient photo album to prove it. That was the second red flag.

Before he got to the blurry Grand Prix photos, he flipped past yellowing boudoir photos of 1970s-era girlfriends and an ex-wife or two—think Farrah Fawcett hair, turquoise eyeshadow, and cheap, nylon babydoll negligees—and a Polaroid of a lovely Irish Setter. I said something like, “What a pretty dog". His reply made me squirm. “Yeah, I accidentally backed over him with my truck one Christmas morning". Merry Christmas kids, dad flattened Rusty. I finished my drink and went home.

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71. Your Insecurities Are Showing

This date wouldn't stop making fun of me. She was 26 and I was 36, but we were at the same place in our careers. Yet, she kept making ageist jokes about how I was old and decrepit. Eventually, after telling her pretty directly to lay off, I just said, "You know, I'm not enjoying this, I'm going to go". I then paid for the table and left.

Later on, she said she was acting that way because she was overcompensating for her failures. She said she felt self-conscious about how much younger she was, but to me, what she was really saying was that when she's uncomfortable, she goes straight to demeaning the other person. No thanks.

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72. A Rose By Any Other Name

I was in a new relationship and everything seemed to be going great. She invited me to meet her friends and I was chatting with everyone. One of the guys and I were getting along, and at some point, I introduced myself as so-and-so’s boyfriend. He excitedly said: “Oh, you must be Jake!” For the record, my name is Anthony.

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73. Too Excited

On my first date with a guy from an internet dating site, he took me to the Scientology museum in London. I thought, "Hmm...That's original; plus, it's easy to find things to talk about, so it could be fun". Boy, was I wrong. He took the museum very seriously. He read every single piece of writing on every single exhibit and asked the attendant very probing questions about how one goes about joining Scientology. He sounded slightly too interested to just be intrigued about a religion. Also, he was visibly sweating.

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74. Family First

I was on a first date with a friend in high school. After we went out for dinner, we went back to his house because he was hosting a bonfire. He introduced me to his father and stepmother, then took me to his balcony. The balcony was easily visible from their living room, which was where his family was. We were sitting on bar stools, chatting.

Suddenly, he stated, “I promised my dad I would always make sure to kiss the girl on the first date". That creeped me out, but not as much as his next move did. He pulled me from my chair and had me so that I was straddling him, and he proceeded to try to make out with me. I stopped his advances and called my friend to pick me up. It was so cringe-worthy because his parents were literally 20 feet away from the scene. We never talked again.

Wildest Things Found Inside Houses factsShutterstock

75. Suspicious Activity

My wife was an operations manager for a big box store and I had suspicions about her friendship with another employee. She was working late and they were texting. I checked her phone and the language was flirty but not incriminating. Her work friend was younger than her and he got accepted to a college in Syracuse.

I was relieved knowing that he would soon be gone and out of the picture, but nope, not what happened. When he moved, she became a recluse and started complaining about going to work. I thought it was just the job making her sad, but really, it was the fact that her coworker was now living in Syracuse. A few months went by and she planned a trip.

She said she needed to recharge. I was excited and naive thinking she would come back as the woman I fell in love with. A day or two into her trip, I got a call from the bank asking to confirm suspicious charges. She had driven straight to Syracuse and the charges were for a hotel room.

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76. Utterly Delicious

My blind date moaned every time I bit into a breadstick at Olive Garden. When I questioned him why he did that, he casually explained that seeing women eating was his own personal aphrodisiac. I had my sister wait at a nearby Target for safety reasons and I shot her a "Come NOW" message. Then I just got up and left.

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77. Three Strikes

My first girlfriend cheated on me and accidentally mentioned his name during a conversation. I didn’t recognize it, so I asked who he was. After poking and prodding, she confessed her unfaithfulness but didn’t feel any guilt over her actions. She maintained this weird double standard where it was fine for her to do what she did, but I shouldn't try anything similar or it would be over.

My next relationship never felt right. We mutually agreed to split because we could tell it wasn't going very well. A couple of days later, she posted pictures from a date she was on with another guy who I actually recognized. She acted weird towards the end of our relationship, but I have no proof that she ever did anything with that guy.

My third girlfriend is a plot twist because she was cheating on me, but with people who I absolutely did NOT expect. She confessed that she had been with multiple girls. I found out because she was low key bragging to her friends. She implied that I didn't like gay people if I wasn't okay with her "fooling around" with her friends. It took me the better part of a year to see the flaws with that logic and had a friend help me end it.

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78. The Proof Is In The Blog

I found out through her blog. I don’t know if she didn’t remember that I had signed up to support her or if she just didn’t care. The blog post gave extensive details about how she finally found “real love in the world". She posted it while on a supposed business trip, which ended up actually being a week-long vacation with the other guy. I shipped her things to the hotel.

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79. Won’t You Be My Neighbor

I didn't even realize I was on a date with this one guy. Years ago, I had recently moved to a new neighborhood and the guy that lived two houses down invited me and my kids to a bonfire. He had a daughter who was just a bit older than my own and he assured me there would be plenty of other people and kids there. When we arrived, the kids all started playing and running around, which was great.

I sat down and started talking to the lady next to me. I thought to myself, what a great way to meet new people in the neighborhood. I was having a great time until the lady started asking me how I met her brother. After explaining that I was his new neighbor, she excitedly grabbed my arm and dropped a total bomb on me.

She said she was so happy that her brother and I got together so quickly. Excuse me? Turned out, he'd told them all I was his new girlfriend, and this was his chance to introduce me to his family. I was trying to figure out if it was an elaborate prank. At some point, he came up behind me and put his hand on my shoulder. He then introduced me by the wrong name, which made it more surreal.

All of these people were beaming at us and all I could do was weakly say, "You're wrong. I just met you four days ago. I've only just moved to this neighborhood two weeks ago". I then grabbed my kids and dragged them home. My kids weren't allowed to hang out with his daughter unless they were with a group of neighborhood kids. I avoided that guy in every way possible and have no idea how he explained my quick retreat to his family.

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80. Momma’s Boy

Before I met my husband, I went on a date with a guy I met on a dating app. He seemed kind of cute and normal, so we decided to meet for coffee at a park. Within five minutes of our conversation, this man mentioned his cat. I like animals, so I asked, “Aw, what’s your cat’s name?” He then gave me a name...along with 14 other names. Yes, that meant he had 15 cats, which he owned with his mom.

Oh, yeah. He also lived with his mom, and the car he was driving was his mom’s, but he was keeping it tuned up. Also, he mentioned to his mom that we were going on a date and he had already shown her pictures of me. Apparently, she agreed that our features combined would make an agreeable grandchild. That one had me speechless. I got right out of there.

A few days later, he somehow found me on social media, even without knowing my last name. He messaged me every day for three weeks asking why I was not answering his phone calls or text messages. So I blocked him. Thinking the worst was over, I moved on with my life...but he just wouldn't stop. He found me on ANOTHER dating app somehow and messaged me on there!

The messages he sent were just super creepy. He kept saying he thought we would make a great couple and that I’d make a great wife. He also said he thought I was so pretty, but suggested I should try going blonde. Weird.

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81. Miscommunication

I went on what I thought was a friendly hangout with an exchange student. I met him playing soccer at the college. He seemed really friendly and kept asking to get dinner. I was single but still mentally getting over my ex who had cheated on me, so I told him I wasn't in a place to date. He said he was cool being friends and that we could still get dinner without any romance involved.

So we went to get dinner. All was fine, but on the way out, he physically picked me up with no warning. I asked him to put me down because I didn't like being picked up. He just laughed it off. He said he'd looked through my Facebook and knew I used to be chubby, but that I looked fine now and didn't have to be so shy about men lifting me.

Obviously, I was incredibly weirded out, but he'd been so nice before, so I chalked it up to cultural differences and brushed it off. I dropped him back off at his house and he invited me in so I could "say hi to his roommates". It was still light out and I'd been very clear about the platonic bit, so I figured what the heck. I instantly wanted to take back that decision.

He steered me to his room, where he got out a headscarf that he told me belonged to his mother. He said his future wife would wear it and then proceeded to TIE IT AROUND MY HEAD.  I awkwardly tried to return it to him, but he insisted that I keep it. I was feeling really creeped out at that point. I wanted to get out of there without setting him off, so I told him that I couldn't possibly accept such a lovely gift with such meaning to his family.

Then he grabbed me, fell backward onto his bed while holding onto me, and tried to kiss me. I shoved him off and started screaming at him, but he just tried to do it again. I ran out of the house while he followed, telling me how stuck up I was. The next day, he texted me and said he couldn’t believe how frigid and dramatic I was.

So, I blocked him. Then, he showed up outside my work when I was closing a few days later with a WIRELESS PHONE CHARGING BRICK because, according to this fool, "I must be having problems keeping my phone charged since I haven't been texting him back".

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82. Child’s Play

This was about a year and a half ago when I was in my twenties. I had just gotten over a man who I'd been dating for four years. He broke up with me after it came out that he was shopping for an engagement ring, and that concept suddenly gave me cold feet. Sometime during my period of being single, a guy asked me out. I had been his manager for a while and always considered him kind of cute.

I had been three months single and there was no real reason to turn down his request for a date. I was a little nervous because it would be my first time out after a four-year relationship, but he seemed sweet and all, so what the heck? I was excited until he sent me an odd message on my phone. He said that, despite owning a car, he let his license expire because "driving scared him". That should have been the first red flag.

I ended up driving an hour to his house to pick him up and he directed me to the nearest shopping mall. I was thinking, "Okay, maybe we're just going to go window shopping, grab a coffee, and goof off". Kind of a teenage thing to do, but maybe I could use something less serious right now. We got there and the first thing he did was point out a sculpture that was...phallic in nature.

He kept laughing about it long after the humor passed. He just kept pointing at it and muttering, "Giant silver eggplant!" Then he walked me straight to the corner of the mall where the Rainforest Cafe was. We walked through the gift shop to where the host was standing, and he immediately requested to be seated next to the animatronic gorillas.

I must have given him a weird look because he turned to me and said, "They're my favorite". We got seated next to a family of rubber gorillas that made awkward robotic motions and he just kept laughing. At that point, I asked him if he planned on getting a drink, to which he replied yes. I asked our waitress to bring me a spiked cranberry, while he asked if he was allowed to order off the children's menu.

She said yes. The next thing I knew, she was bringing back one spiked cranberry, and one child's plastic smoothie holder with a giant, cartoon orangutan head as a lid, from which a pink silly straw was protruding. It was filled with chocolate milk. "I, uh, thought we were both getting a drink?" I asked, feeling kind of sheepish because now I looked like I was a mother.

"Yeah, I don't really like drinking. And this came with a toy I wanted," he said, showing me that you can twist off the bottom of the cup and there's a plastic monkey inside. He spent the rest of the meal trying to convince me that we should tell the waitress it was my birthday. His reasoning was so we could get a free sundae with a sparkler on top because sparklers are so cool.

I, on the other hand, spent the rest of the meal using my cocktail napkin to casually wipe away tears of regret. Then I drove him home.

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83. Our Little Secret

I didn’t realize I was logged into my girlfriend's Facebook. She had used my computer and we had a lot of mutual friends. At one point, I got a message from one of her friends asking how it went last night. When I opened the conversation, my jaw dropped. Her friend was excited to find out if she stayed behind and if he finally saw my exes’ underwear. It took a minute for everything to sink in.

I went for a run and waited for her to wake up. We broke up in an amicable conversation and I didn’t tell her what I had found out. As far as I know, she still has no idea what prompted me to end it. We had been together for three years and we were both miserable. I wasn’t angry; I was just surprised that it came down to a Facebook message for us to pull the plug.

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84. You’ve Got Mail

I had this intuition four years ago to check my exes’ email. There was nothing strange about his behavior and we weren’t going through a rough patch; it was just a strong urge to log in. We had each other’s passwords and when I opened his inbox, there was an email from his ex. He had responded to it that morning telling her how much he missed what they had.

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85. Toe Thanks

I went to meet a guy for the first time at his house. I liked him a lot, but when I got to his place, I was immediately turned off by what I saw. There was a pile of toenail clippings on his coffee table. And it wasn’t one recent clipping. It was like, many clippings. I went straight back out the door.

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86. Don’t Dare Compare

After my freshman year of college, I met a guy on OK Cupid and we went to get dinner. He offered to give me a ride, but I said no. He was a couple of years older than me, so I felt unsure. At dinner, he started talking about how he'd started his own business after college and how it was going well. Good for him!

He bragged a bit, but hey, that's an accomplishment. After we ordered food, he said to me, in the creepiest voice ever: "Let's play a game". He wanted us to take out our wallets and compare what was in them". It wasn't a joke. He literally started showing me his credit cards and bragging about the high limits. He ended with, "Clearly you can't afford to pay for this dinner, but don't worry, I can cover you".

I was mad and protested, but he wouldn't take no for an answer. As we left, he said he wanted to show me his car. Unfortunately, it was nearer to the restaurant entrance than mine was, so I had to walk by it. It was a white, windowless serial killer van. He begged me to get in the back with him, right there in the parking lot. I was pretty glad I drove separately.

Customers paying waiter at restaurant.Getty Images

87. Eat Fresh

I went on a date with a guy that I met online. He told me to dress nicely as he was going to take me out for dinner. He took me to Subway and ordered a foot-long teriyaki chicken sub. He then looked at me and said, "I hope you like teriyaki chicken". We shared the sub in his car. Safe to say there was no second date.

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88. Nay To PDA

I went to meet a woman in her 30s at a Starbucks. I showed up to see a woman pushing 50, maybe more, and she was much larger than she initially claimed to be. She immediately started to talk about getting intimate with me, asking me what positions were my favorite and stuff like that. This was in the middle of a crowded Starbucks where there were children around.

She then reached across the table and tried to grab my hand and touch me, to which I told her that PDA makes me uncomfortable. This was a lie, but I didn't want to cause a scene or hurt her feelings.  I told her that I wasn't feeling too well and that I should probably go. I thought that would be the end of it, but my nightmare was just beginning.

She followed me out, grabbed my butt, tried to push herself against me, and tried to kiss me. I told her again that I was not comfortable with PDA, and after several repeats of this, she finally let me get into my car. I got out of there as fast as I could and took some time away from the dating scene after that encounter.

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89. Beyond Inappropriate

I met a guy through a dating app and we got on well, so we decided to meet up. We had a nice lunch, then we went for a walk around the city. Everything was going well until we passed through an alley. He stopped walking, looked me in the eyes, and said the freakiest words I'd ever heard on a date. "You look so good, I really want to jump you right now".

I thought I'd misheard and asked him to repeat it, and he doubled down: "I want to throw you down and jump you right now!" I told him how messed up that was and said I was going home. He caught up to me and said he was only joking. Just before my train arrived, he said it AGAIN, and that it was my fault for looking so good.

I told him we were done and not to call ever again. I got texts the rest of the week saying I was being immature, couldn't take a joke, and was "probably a tease anyway".

Awkward Crush factsShutterstock

90. A Stalker Confession

My wife told me a guy from her work was stalking her, so I told him I knew what he was doing and that he needed to stay away from her or else. But here's the crazy part—he had no idea my wife had accused him of stalking her. He assumed I was talking about the affair they were having. It freaked him out and he immediately went home to his wife and confessed.

My wife was just trying to get me to get rid of him for her and hadn’t told her jilted lover the alibi she was using. It had been happening for a while behind both of our marriages. After he confessed to his wife, she called me in tears and asked how I know about the situation. It was a confusing conversation until I realized the truth of the situation.

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91. I’m Just A Fun Girl

We got engaged the summer after I graduated college. We had been dating for five years and I had to move home for work for six months. I noticed she started acting withdrawn. My attempts to talk to her on the phone while I was away were described as smothering. She wasn’t acting like herself so I began to investigate.

I started checking the phone bill for numbers she was texting and looking through her emails. I didn’t find anything and I thought I was paranoid, but then in January, I found an incredibly telling piece of evidence. It was an email that I found in her outbox with no trace of prior conversation. She wrote to another man that she’s in a relationship but she’s looking for someone to help her be a fun girl.

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92. Drama 101

My wife got invited to a client's daughter's wedding. The couple were both drama students and many of the bridal party were drama students. The maid of honor's toast was so disturbing, it’s unforgettable. It consisted of tearful declarations of unrequited love to the groom, along the lines of “if it couldn't be me, I'm glad it's my best friend that's marrying you".

Somehow, that’s not the worst part. The best man's speech was a lusty declaration of “if it doesn't work out, call me, the previous time you called me". Other toasts were similarly weird. A guy at the table I was seated at was a friend of the bride and said to me that he was “this close” to standing up during the “speak now or forever hold your peace” thing.

I'm still not sure if the whole thing was a bunch of emotionally messed-up 20-year-olds, or one big piece of performance art.

Marriages won't lastUnsplash

93. By My Calculations

We were in college and she told me she was pregnant. We weren’t sure what to do besides schedule a doctor’s appointment. I was all-in for her, ready to step up to the plate for her and our child...until the doctor told us a key piece of information that turned everything upside-down: the estimated date of conception. I realized that I was out of town during those dates, so I questioned her about it. She confessed to sleeping with my roommate while I was out of town.

Cheaters ExposedShutterstock

94. Crying Over Spilled Champagne

One of my good friends got married and I'd never met the bride before the wedding because "she's just shy". On the wedding day, she was belligerently inebriated before the ceremony even started and couldn't even get through the lines she was supposed to repeat (i.e. "I promise to love you"). She ended up slapping the groom, spilling champagne on her dress, and then crying under a table while he tried to comfort her.

They lasted about four months.

Marriages won't lastPexels

95. Girl Code

I was dating this girl for almost a year and it was serious. I was friends with her mom and most of her friends but she was a very jealous and possessive person. One night, I was at her house and she got into the shower. I was on the floor playing with her iPad when I noticed a book under her bed. It looked like a sketchbook at first, so I grabbed it.

I opened it thinking I would see beautiful sketches, but it was her diary. The words on the pages gave me shivers. She wrote about how she had been cheating on me with multiple men. It was shocking because she was so jealous and possessive. I calmly closed it, put it back under the bed, and left. I called one of her friends with who I had become tight with and asked her to explain.

She agreed to meet me later, meanwhile, my girlfriend got out of the shower and asked why I left. I told her I read her diary and that it was over between us. She tried to be angry about me for reading the diary but she was more upset that she was caught. I met up with her friend for coffee and she told me everything. My girlfriend and three of her friends had made a pact.

They were all in on it together and they would travel, party, and create a lot of opportunities. They’d rent hotel rooms together, cover for each other, and made detailed notes so no one found out. Her friend wanted to come clean as she was over it. She didn’t feel good about lying or hurting people, and the guilt was unbearable.

Cheaters ExposedShutterstock

96. Child Bride

I used to work at a David's Bridal and a bride came in once with tons of friends. We did the Say Yes To The Dress thing, and an hour later she was standing there in $3,000 worth of stuff and didn't have any money with her or in her account. She decided she wanted to apply for the store credit card. I ran it through the system, and she got denied.

She then called the groom for his info and he told her no. She threw a HUGE fit on the phone with him, standing on the bridal stage, literally demanding "WHY NOT? WHY?! WHY!!" like an actual child over and over again. I've never seen a 30-year-old age backward so quickly. She was just a brat. Literally stomping her feet in front of me, all her friends, and the other brides in the store.

I was so embarrassed for her. But then I got a big surprise. At the end of her tantrum, she hung up on him and her friend said, "I'm so sorry you can't get your dress". The bride stopped crying instantly and said: "Oh I'll get the dress. I just have to do this at home, and when he gets mad enough, he'll come get it for me so I'll stop".

I was speechless. Sure enough. Girl came back two days later with her man and he applied for the credit card and bought the dress. He was livid and silent, and she was over-the-top smug. I can't imagine they're having a happy marriage if they are still together.

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97. Alexa, Restart My Heart

We had been married for a few years and it was great, but once we had a baby, he panicked. All of a sudden he didn’t know what he wanted. Eventually, he asked me for space. We still spoke but he wasn’t involved with our baby or fixing our marriage. Ten months later, I added a new Amazon Echo to our family Prime account and I noticed a device I didn’t recognize.

I figured out that the device was set up at the place where he was currently living. Since it was linked to our account, I was able to go through voice requests and play them back. One recording sent chills up my spine. It was my husband saying, “Alexa, play beautiful love songs” while in the background I can hear intimate noises. Turns out, he was having an affair with a colleague.

They’d been having an affair since at least the birth of our daughter, but lots of clues say it started before. It was easier to end it considering how long he had already been gone. When I originally shared this on social media, it got picked up by a tabloid newspaper with the headline ‘Amazon Slimeball’ which is now what he is saved as in my contacts forever.

Cheaters ExposedShutterstock

98. Red Flags

He was about 11 years older than me and I was only 19 at the time. I didn’t have a car, so he picked me up from my apartment. We went out to dinner and it was kind of awkward, but we had plans to go bowling after and I was too shy to cancel the second half of the date. So I just went along with it. Everything was fine until he said he got "lost" and didn't know how to get to the bowling alley.

When I saw where we were actually headed, my heart dropped. He drove me into the woods in complete darkness. I really thought I was about to be hurt. I didn’t think it was just my anxiety, as he got really creepy and there was something seriously sinister about his demeanor while this was happening. But after a tense drive through the woods, we eventually got to the bowling alley.

I said I wasn’t feeling well and went to the restroom. When I came back out, I told him I had thrown up and that I wanted to go home. Thankfully, he did actually drive me home without getting “lost" again. I ghosted him after that, but he somehow found my email and sent me a message about how horrible I was for ghosting him.

Honestly, I was just glad I made it out alive. I moved as soon as I could because he knew where I lived. Now I ALWAYS meet people on the date, not at my apartment, and I take Ubers.


Creepy DatesShutterstock

99. The City Of Dates

I had just moved to San Francisco from college and started talking to this guy on Tinder who was in his late 30s/early 40s. I hadn’t had much luck with older dates previously but I decided to be more open-minded. We got cocktails and on the date, I acted as pleasant and engaged as I could even though there was not much chemistry.

After one drink we decided to part ways, and he offered me a ride home. Once I got home, I received a message that was paragraphs long from him! He really wanted to leave the whole time but stayed to pay for my drink and give me a ride home. He also let me know I was overweight, unattractive and I had acne that was disgusting.

My heart sank after this unprompted and completely unnecessary message. I immediately deleted it and blocked him but the words still replayed in my head. Even now I still think about it, and it makes me sad that I dimmed my light because some guy decided to be awful.

Embarrassing datePexels

100. Solemates

His mom wanted to put his socks on for him. And he let her! This fully capable, adult male actually sat there grinning at me quite happily while his 50 something-year-old mother knelt before him as if he was a demigod. She then proceeded to lovingly roll his socks onto each of his feet! Noped outta there? I'm still running!

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101. Welcome To “The Family”

My first girlfriend was a nice Italian girl whose family drove me crazy. I'm a white-bread Canadian; what one might call a "mangia cake," so that was the first strike against me in their eyes. Her mother treated me well, but the dad always looked at me as if I wore my shoes in the house or something. The first time I had dinner at their house, he went into a whole speech about the etymology of the word "wap," unbidden by anything I had said or done.

Oh, and we had to take her younger brother on dates with us. This one time, he made plans with some friend so we could drop him off and get some alone time…and he immediately ratted her out when he got home. Then, another time we were out on the porch with my arm around her shoulders as we watched the sunset. Her father came out and made some meaningless small talk about how the weather was so nice and that it was so nice to have such a warm evening.

I found out the next day that he beat the heck out of her for being “loose” in "public". We talked about getting her out of that house, but at the end of the day, she couldn't leave her family behind. We were only together for a few months, but the whole family situation was just something I couldn't deal with. And then came the icing on the cake.

It was my birthday and she went and gave me a Rolex. Again, we had only been dating for a few months and I had already been to her house many times, so I knew she wasn't from some wealthy family where money was meaningless. Still, she assured me it was a genuine Rolex that her father had "acquired".  That was when I learned that he was a local mafia boss and more than a few pieces fell into place.

I thanked her for the gift but gave it back as I didn't want to feel like I owed any favors to anyone. We broke up soon afterward. The next time I saw her has at a friend's wedding where she was there with her (very Italian) fiancé.

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102. I’m Gonna Getcha

I was dating this girl who asked me to go to her ex’s wedding. We dated for a few months prior, but asking me to go to a wedding together felt like a serious commitment...I still accepted. I planned for the week off work and we went all out for this wedding. Half the time, I was trying to make the most of our time together, but she always went missing.

Fast forward to the reception. She made a scene in the most unstable and mentally sick way. In front of the groom, the bride, and everyone else, she said out loud: “I’m still in love with you. We literally have been sleeping together all week and I can't stop thinking about you". She quickly got escorted out after that.

The bride was clearly upset, but everyone tried to go about their business. As soon as I left, my “girlfriend” started completely ruining the hall and all the decorations, just throwing a fit on her way out. It was so embarrassing. I figured she was telling the truth since she was missing the whole time, but I’m pretty sure that everyone during the whole thing assumed this was too crazy to be real.

I definitely regret not seeing her true colors before, but when you work so much and try to date at the same time, you have very little time to get to really know some people. Time sort of flies by and you end up dating for a few months. Fast forward a month or two later...she got together with the groom and I’m pretty sure she has no regrets about wasting my time.

She probably doesn’t even feel bad about using me or even ruining that man’s marriage. This woman is seriously twisted.

Weddings Gone WildShutterstock

103. Long Hand Of The Law

In high school, I was dating this guy, and everything was going great. I was infatuated with him. A few months into our relationship, we slept together. It was both our first time. He was holding me and kissed my forehead. Then he said something that made my skin crawl. He told me that he wanted to cut my skin off in the shapes of stars and put them in the sky.

That was so he could always see a part of me. He said this as he cried and bear-hugged me. I didn't know what to say, and when I went home that night, I called him and ended things. For the next four months, he waited outside my classes and got his friends to come to talk to me. And he just turned really angry and petty.

He posted fliers around school calling me names. I came home crying, and my dad was absolutely livid. All he told me was that he would take care of it. My dad was an officer and my ex's dad's boss. He had me tell him where my ex and his friends hung out after school, and he and his partner drove their patrol car over.

One of the boys ran, but my dad's partner caught up and dragged him to the car. My dad then made all four boys cry. Later, I got a call from each kid apologizing. My ex avoided me the rest of high school like the plague.

Crazy ex boyfiendsShutterstock

104. Cheaters Never Prosper

I knew my ex wife was cheating but didn’t tell her that I knew. Took her out for a dinner date and I casually asked questions about who she had been spending time with while I was at sea, she barely worked so she had to spend her time doing something. She failed to mention the guy that had been staying at my house for nearly two months.

This was the same guy she had to call the authorities on just to get to leave because I was coming home in two days... soooo I slid her a copy of the official report that was filed for the incident and watched as she crumbled over the fact she had been caught, and I didn’t have to say a word.

Caught Lying factsPinterest


Sources:  1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13,

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