You only have one chance at making a good first impression. When you’re on a first date, everything you do might be heavily scrutinized. This might make some people self-conscious, but these bad dates didn’t seem to care that their terrible behavior had the potential to ruin their chances. These dealbreaker moments take cringeworthy to the next level.
1. Lesson Learned
When I was young, I landed a date with my dream girl. She was beautiful. 10/10. We exchanged numbers earlier in the week and agreed to go out on a Saturday. The Thursday night before was the first time we stayed up late, just chatting. It should’ve been a dream, but it was actually a nightmare. Throughout the whole conversation, I don’t think I said more than two words in a row.
It was all one-sided—and that’s not even the worst part. She spent most of the time complaining about other people. That’s was the dealbreaker. When I saw her do that, I realized that looks are just looks and personality means a whole lot more.
2. Some Heroes Don’t Wear Capes—They Drive Taxis
I went on a first date a few years ago. He took me to an exclusive members-only club, bought the most expensive bottles of wine, handed me his wallet to pay for them, then excused himself to go to the bathroom. It was all so I could see how much money he had. Yup, he had well over £2,000 in there. I thought that was weird but I just chalked it up to him trying to impress me in a weird way. I wasn’t impressed—but I also wasn’t prepared for what came next.
After that, he took me to a strip club where the bar staff knew him by name. I was incredibly uncomfortable, but it got even worse when two of his friends just “coincidentally” bumped into him at the club, sat with us, then hired girls for private dances three feet away from us. I stayed for five minutes, then excused myself to go to the bathroom.
The plan was to come up with an excuse to leave. I returned, took another sip of my champagne, stayed another five minutes, then simply said I had to go. They tried everything they could to get me to stay, but I refused. As soon as I stood up, I felt lightheaded. That’s when I made a truly disturbing realization.
They’d spiked my drink. I panicked and walked off, with my date following me, desperately begging me to stay a little longer. He then offered to get in the taxi with me and escort me home. Even though I refused, he still tried to get into one with me. We had a heated conversation where he kept offering to escort me home and I just kept responding with: “I’m a big girl and can take care of myself.”
The taxi driver must have sensed that something was off because he intervened. He told him I’d said no, and that was that. He drove off, asked for my address, and got me home safe and sound. By then, I was passed out in the back of the taxi. I don’t remember how I got indoors, but I remember waking up on the bathroom floor the next morning feeling perfectly fine.
In the voice of Comic Book Guy: Worst. First date. Ever.
3. The Cell Block Tango
After chatting with a girl on an online dating app for a while, I went to her house for the first meeting. I felt this was a strange request on her part. We were in deep conversation when I noticed that she was wearing a tracker on her ankle. That’s when she was forced to tell me her twisted story. It turned out, she was under house arrest because she was awaiting trial.
When I found out the reason why…my blood ran ice cold. She had been accused of killing her husband. If I hadn’t noticed the tracker, I’m not sure whether or not she was ever going to say anything otherwise. I was told a very detailed story and it was apparently some sort of accident. I couldn’t get out of there fast enough.
4. Covert Operations
Once, I went on a first date with a guy from my school and we decided to head back to his apartment. On the way up to his floor, he was acting really sketchy. He kept looking around for people and peeking corners. When we finally got to his room, I found out the chilling reason why. He said: “Glad no one saw us. My ex has spies and she would come if she knew you were here.”
When the date was over, I also had to sneak out on my own, because apparently, one of his suitemates was a spy for the ex. He coached me to respond, “I’m just getting some calculus homework I missed during the week,” should anyone see me and ask why I was in his room. The guy was fine, but I was not about to deal with his psychotic ex.
From the absolute paranoia he had shown me, I knew that he’d been through some stuff with her.
5. If I Could Turn Back Time
I went on a first date about a year ago. We met for lunch on a workday but I have a flexible schedule. She was 30 minutes late and then for some reason, she parked three blocks away, even though the place had an empty parking lot. It took her another 15 minutes to walk to the restaurant, which I thought was kind of annoying. But then, during lunch, she mentioned the reason why she was late for the date.
It was because she just had to stop at Target and Starbucks. We still had a good time, but after two hours I told her that I had to get back to work. I asked her where she parked and she told me. I offered her a ride to her car and she said no. About an hour later, she texted me. I couldn’t believe what that message said.
She told me that it was rude that I didn’t walk her to her car. There was no second date.
6. Read The Fine Print
I met a girl online and our conversations were going well. We lived in the same state, but we were still two hours apart. We knew were aware of this—or at least I was since the info was in our dating profiles. After two weeks of chatting, we finally set up a date to meet. That’s when she realized where I lived and she flipped out, claiming that I was too far. We stopped talking after.
7. Empty Vessels Make The Most Noise
She showed up late because she was “getting all done up,” as she told me over text. But when she got there, she was in a ratty hoodie and her clothes smelled…musty. She was super shy, quiet, and barely spoke, even when asked innocuous questions. That is…until the movie started. Then she wouldn’t shut the heck up. She kept staring at me and asked the dumbest questions like, “How’d you get so tall?” and “Do you like movies?”
8. Crash And Burn
I went out on a first date with a guy who I had been talking to for a while. When we finally met, we went on a walk around the local zoo and then went to get some drinks. We were having a good time, though he brought up his ex-fiancée a few times. I don’t usually care, but eventually, it started raising red flags for me. I should’ve listened to them.
At some point, we decided to order another round of drinks. No big deal. About halfway through—boom. I could see him spacing out, repeating himself, slurring a bit. I hate being around people like that when I don’t know them, so I thought maybe I was just being a bit harsh. Cut to him being almost done with his glass—he stood up at the bar next to me, screaming about how his ex just bought a car.
Then, he yelled that she should be with HIM. He rambled on about how his sister always told him he’d never find love because he was so hung up on the ex. Eventually, I went to the bathroom and he paid the bill. I waited ‘til he walked out and ordered another drink for myself. It was the most awkward thing I had ever been through.
9. Dating Dr. Atkins
I went on a really bad date a few years ago. He took me to a restaurant and decided he would order for me. At first, I let it slide because I had never had Indian cuisine before, and thought that maybe he was just trying to show me a good dish. When the meal came, the waiter brought along some rice and naan. As I reached for the naan, he pulled the basket back and said something so rude, I’ve never forgotten it.
He told me, “Oh no, you have enough carbs on your plate.” I told him I wasn’t hungry anymore and asked for the check. As we left, he tried to force a hug on me, which I rejected. I swiftly got in my car. He sent me like 20 messages through Snapchat and called me five times, all within an hour after that. I was annoyed at the whole situation, but at least I still got my revenge.
I told my friend about it, and she completely blew up his phone with pictures of bread. I’m glad I’m not dating anymore.
10. Five-Star Uber Driver, One-Star Date
I remember this one guy I went on a date with. We literally just started talking that same day and he already wanted to meet up for lunch. I told him, “Sorry, I’m busy. I have an interview at 2 pm, so how about two days from now?” He replied, “Oh, it’s cold out, I can pick you up from the interview.” Um…no thanks. Then, he asked me: “What are you doing tomorrow that makes you so busy we can’t meet?” None of your business dude. This just kept going on and on.
From the start of our convo at 9 pm, it took me until 4 pm to just flat out tell him that I didn’t think we’d be compatible…which then warranted a hundred more questions as to why, as well as explanations on how much of good a man he swears he is. I was exhausted. I couldn’t even imagine that level of intrusiveness if someone actually WAS his girlfriend.
Imagine having to go to the bathroom. “Babe, where you off to?”
11. “Never Again” Doesn’t Quite Cover It
So I met this chick online. I was having car troubles, so this particular night, she was my ride. She picked me up and we went to a mall. She seemed really cool, and we were hitting it off. We went to the Sbarro’s at the food court and got a bit of lunch. We were sitting there eating, and all of a sudden, she said something completely out of the blue that threw me off-guard: “My ex beat me.”
I was literally mid-bite. I had a little moment where I stopped chewing for a moment and then started chewing again really slowly because I had already committed to the bite. I replied, “I’m…sorry, that sucks.” She replied, “Yeah, we just broke up a week ago.” Yikes. Not only was she damaged, but I guess I was also a rebound. Great. I did feel bad for her though. But she just kept talking, and talking, and talking about nothing but her relationship with him.
At that point, I was already thinking, wow, this is a really terrible date. But it just got worse from there. She went on to tell me a story about how she told him she was going on a date with me, and he grabbed her arm and yelled at her. In my head, I was like, “What in the heavens have I gotten myself into?” I just wanted to nope out of there, but she was my ride. I had no choice but to stick around.
As walked around the mall, she stopped us and said, “Hey, let’s go into Hot Topic. I LOVE this store.” Sigh. While we were in there, she just lunged at me and kissed me. It was weird, but I just shook it off. Sometime later, I eventually told her, “Okay, well I had a really good time!” What she said next was…chilling, to say the least. She said, “Me too! You’re so great. I can’t wait for my family to meet you.”
I didn’t know how to respond to that, so I just defaulted with a smile and a nod. Obviously, I would never let it get to the point where I would meet her family. But then the worst happened. As we left the mall, she started to go onto a highway that I never, ever went on. I asked her: “Where are we going?” She replied: “To my house, duh!” Apparently, she meant “I can’t wait until you meet my family right now.”
At that point, I almost wanted to call a friend for a ride, but my friends would have loved the fact that I was in this situation. I decided to stick it out. I figured, okay, just survive a couple of hours, and then she’ll take me home. Nope. We got to her house, and almost immediately, her mom asked me to help her move a pile of six or seven heavy boxes out to the shed in the back yard.
I was too polite to say no, so I did it. I came back in, covered in sweat, muscles aching, and she said, “Thanks, sweetheart.” The girl’s brother then walked into the room and she introduced me to him. “Hey, this is my brother. He’s really autistic, so don’t pay any attention to him.” I said, “What do you mean?” She replied: “Well, everything he says is weird, so you just take it with a grain of salt.”
I really felt bad for the kid. He was interesting. He showed me his lizard and tarantula. He changed subjects all over the place and it was really hard for me to follow, but he eventually left to go do something else. After spending an hour watching TV and doing nothing with the girl, she asked me, “So are you ready to go eat?”
I should have told her I just wanted to go home, but I chickened out. We got ready to leave for Chili’s and her mom walked into the living room with her purse. “So, where we going??” I laughed. Seriously, I thought she was joking, because what mom would just invite herself to dinner on her 23-year-old daughter’s first date with a guy? I should never have underestimated this family.
She looked at me weirdly, and then back to her daughter. “Chilli’s. Is Terrance ready?” So she already knew where we were going…I guess they’d conspired about it. We go to Chili’s, and I felt like I was the big brother in the family. There was constant bickering between the brother and sister, with her egging him on, making fun of him for being autistic, and the mom only jumping in when they started kicking each other under the table.
After about an hour, we left. We got back to their house, and it was about 10 pm. I figured we were dropping off the mom and brother so she could take me home. “So, you about to take me home?” The mom suddenly jumped in. What she said was so disturbing, it’s unforgettable. “No, she’s not allowed to drive after dark. You’ll have to spend the night. It’s okay, though. Her bed’s a queen, and I don’t care what you guys do in there. I’m not the strict type.”
I was ready to call a friend because I was seriously about to panic. Not that I feared for my safety, but I was just at a 12 on a scale of 1-10 of discomfort. I pulled out my phone and it was dead. My phone was dead. Why was it dead? OH YEAH, I’D BEEN ON A TEN-HOUR DATE. I figured I would just…have to deal with this. We went back into her room and watched TV.
She kept putting moves on me; moves that were honestly incredibly hard to resist. I ended up pretending to fall asleep, and she fell asleep. I turned the TV on and watched Comedy Central until the infomercials started, and then I got up. It was way too uncomfortable for me to sleep in that situation. So I went into the living room and no one was there.
I started digging through their drawers and cupboards, looking for a charger that would fit my phone. There was only a USB cable, so I had to turn on their computer to charge my phone. I then called a friend. It was about 3 am at that point, so no one was going to pick me up, but I just needed to rant. I talked to her for a couple of hours about my night. I then eventually fell asleep on the couch.
The next morning, after watching like three hours of the Disney Channel, she was finally willing to take me home. I said nothing to her the entire way home. I wanted to just go off on her, but I sensed a lot of crazy in that family, so this was one of those situations where I found it okay to just never answer the phone calls or texts again.
After I ignored her, she ended up convincing a friend to contact me on the dating site. After we swapped numbers, she called me and the girl who I’d been on the date with was there. She yelled, in the background: “NOW ASK HIM WHY HE WON’T TALK TO ME!” I hung up and deleted my profile on that website.
12. A Two-Horse Race
I met this guy at a party. I’m pretty shy, so I ended up kind of hanging out in a corner by myself. At some point, I ran into a guy who was also a friend of a friend. He was pretty cute and funny, so we spent most of the night talking and the next few days texting and calling each other on and off.
Finally, he invited me out on a date to go horseback riding. Cool, I love horses. I’m down. We lived in a bigger city so we had to drive for about 1.5 hours to get to the place where he boarded his horses. On the way there, we chatted and seemed to be hitting it off. Bu then, about 15 minutes away, then he got really quiet. When I looked back, I knew that was the moment I should’ve run.
We got to the place and he literally hopped out of the truck before he even put the car in park. He RAN towards the stable, calling his horse’s name. I put the car in park, thinking that it’d probably been forever since he’d seen her.
I followed him to the stable where he fed her carrots and lovingly stroked her nose. He gave me a carrot and showed me how to position my hand to feed her. The horse then eyeballed me, turned her head, and walked away. Whatever. Afterward, he loaned me a horse to ride, and we went on a mini ride and picnic.
Anytime he got close enough to touch me or hold my hand, his horse would “mysteriously” veer away from me. After we were done, we piled into the truck and made the drive home. About a mile and a half from my exit, he asked me what I thought of his horse. I said I thought she was beautiful. Then he dropped a bomb on me.
He said that he and his horse were in love. The only reason he was dating was that he knew he was going to die before her. He told me that if we were to date, I was not to make him choose because he would always choose her first as she was his priority. In other words, I would be second fiddle to a horse.
I’ve had some pretty awful dates, but if I ever top that one I’m joining a convent.
13. Mamma Mia!
I met a guy online. A little older than I would have liked, but I didn’t think anything of it. I figured hey, it’s just coffee, if anything goes badly I always have a bail. I got there, and the dude was a guido. An older guido. He had a fake tan that made him look like a leather-wrapped mummy. He was balding, wore obnoxious bling, and had his shirt open to show off his chest hair, the works.
I thought it would be rude to stand him up, so I gave him a chance. Well, it turned out, the guy had a child he’d never mentioned to me before. He insisted on buying me more coffee drinks. I watched those like a hawk, but he never slipped anything into them. He went about how he was retired—even though he initially told me he was employed full time—and how he wanted ten more children. Um, nope.
I started hedging out of there, claiming that I needed to go meet a friend somewhere. At that point, I was about to claim my cat was on fire just to escape. That’s when he grabbed my arm and tried to convince me to go home with him. I dropped his arm on the table fairly hard, apologized when he let go in pain, and then dashed.
That was the creepiest guy I’d ever met. Thankfully, I gave him a Google number, not my real number, so I just disabled that number and never heard from him again.
14. Stage Five Clinger
I went out with a guy who bought me a toothbrush after a third date so I could use it when I stayed over at his house. Sweet, right? Well, it quickly spun out of control. He wanted to see me every day of the week after the first date and he’d get insulted if I denied him.
Then, he would demand every little detail regarding what I did when I was not seeing him. “I’m just not that social person and I don’t want to see anyone 24/7 for four days in a row” wasn’t a good enough reason for him.
15. How To Lose A Guy In One Date
The worst date I ever had was actually my first date ever. It was super awkward asking her out, but I told her I’d never asked a girl out before. We made plans to meet up for lunch at a burger place. I paid for the meal ahead of time and we sat down to eat. I began to eat my food, but she barely touched anything, telling me she ate beforehand.
You know…because when you’re meeting someone for lunch, you don’t want to eat with them. She then talked about her job at Starbucks and how she spit in drinks and gave rude people who asked for decaf regular caffeinated coffee. She also told me about other gross things like how she picked her nose and put it in the food, etc.
She also had the audacity to remind me that we would not be getting physical. I remind you, this was my first date with a girl ever. She knew this, yet she still felt the need to warn me…as if somehow I was giving her the signals that I needed to do it with her right then and there.
She checked her phone multiple times, texted people periodically, and seemed to be having a more interesting conversation with someone else. She went on about how ugly and fat she was, which she wasn’t. I tried to tell her different, but she just got offended. She then went on and on about how badly she wanted to date her celebrity crush.
I felt like I was not talking to a real person. It all seemed like the plot of a Kate Hudson movie or something. I was pretty well convinced that it was not going to work. Eventually, the date ended—I think it was only an hour or so, but it felt like so much longer. After that, she was still texting me, trying to make plans to go out again, but I just couldn’t.
Since it was my first date ever, I didn’t realize how bad it was until I went on more dates. Then I realized what a horrible date she was being.
16. The Pre-Screening
This all happened before the first date. He kept asking unnecessary, almost invasive questions about my dating history, but wouldn’t answer the same questions when I threw them back at him. Instead, I got some passive-aggressive statements like, “I don’t go on dates with multiple people just to keep my options open,” as if he wanted me to clarify that I also don’t do that.
When I realized the questioning was only going to be one-sided, I started giving vague answers. He then commented that I seemed disinterested in him because of this. At some point, he started talking about how he wanted a long-term relationship. He blocked me when I didn’t respond for a while, but good riddance—it was taking up way too much of my mental energy anyway.
Of course, he unblocked me the next morning. This was met with a swift block from me. This was all before we had a conversation about literally anything else. If the level of mind games was that strong at that point, then I couldn’t even imagine what a first date would look like.
17. Firework Or Grenade?
Once, I met an Irish girl. She was super nice—we went to an open jam, back when humans convened in indoor spaces without fear. She wanted me to play “Firework” by Katy Perry, as I’d mentioned that I do a pretty decent version. Sadly, the band didn’t know it, and she assumed that I had purposefully not played it—all for the most bizarre reason.
She thought that I didn’t want to do it because I was in love with the married bass player, whom I’d just met. Did I mention that her husband was also playing with us? That argument was thrown at me mere weeks after we’d met, and it was only the second time we’d hung out. Sometimes, it takes several poor choices to see one clearly.
18. Hands Off
I had a guy who tried to constantly grab my hand. It felt like he was trying to maintain some kind of power over me. No matter how much I shifted my hands or tried to make my hands busy by holding a drink or something, he kept grabbing them. So then I put my bag on my lap… That’s when he took it to a whole other level. He tried to grab my leg and work his way up my thigh. Not romantic at all, and very off-putting.
19. Warning Bells Are Ring-ing
I met a girl at a party and noticed a ring on her finger right away. We were flirting, so I asked about the ring and she told me: “Oh yeah. I’m holding it for my friend because she just wants to feel single for a night and have fun.” In my dumb little overeager brain, I was like, oh, okay, that makes sense. So I kept talking to her. We messed around and she gives me her number.
The next day, my Snapchat automatically synced her number and I discovered her dirty little secret. I saw that she was at a BBQ with her husband and kids.
20. Modus Operandi
I had a guy take my hand, look deeply into my eyes, and loud-whisper: “I think I’m falling for you.” It wasn’t a date and he had a girlfriend. He was initially shocked when I immediately wanted to go home, but he later kept trying with me. He was being weird to the point where his girlfriend thought he was officially cheating on her.
She and I talked, and what she told me broke my heart. Apparently, he’d won her over with the same “romantic” tactics. I guess that works for some people.
21. If It Quacks Like A Duck…
A classmate set me up with her sister. I saw a picture and she was a really hot blonde girl. After talking for a bit, we decided to meet for coffee. She showed up in Docs, a Chelsea haircut, suspenders…you know, a look that signifies a certain kind of person. I gave her the benefit of the doubt and assumed she was just into punk or the ‘rude girl’ style. I was wrong.
Ten minutes into our conversation, she told me, “I’m really glad you’re white. From your picture, I thought you might be part beaner or something.” I put down two dollars for my coffee, said “Screw you,” and left. My classmate went out of her way to avoid me the following week, but then later apologized. She said she had no idea that her sister was that messed up.
22. Just A Hop, Skip, And An International Flight Away
Once, I was talking to this girl online. Things were going pretty well, so we decided to go out for dinner. I showed up at the place five minutes early and waited for her to arrive. Then I waited some more…and some more. I texted her 15 minutes after we were scheduled to meet, but didn’t get a response. I waited for another 45 minutes, then left. She messaged me later and told me the reason she hadn’t shown up.
My jaw dropped to the floor. She said that she wasn’t there because she lived in Indonesia. I live in New Jersey.
23. Fools Rush In
I had a blind date with a woman and everything went amazingly well. We were on the same wavelength and it was turning out to be one of the greatest nights of my life. A couple of days later, we went out on a second date. As dinner ended, she looked at me and said she was having a great time and that she really liked me. She then asked me how serious I was about our relationship.
I was stunned at first, but then looked at her and reminded her that we were just on our second date. She said that at our ages—we were both mid-30s at the time—we knew enough to know what we were getting into. She wanted to have a family and have kids, and she did not want to wait. She said that I was the one she wanted to have her kids with.
I sat there dumbstruck. When I didn’t answer immediately, she pushed again. I just said that we should take it slowly and see what happens. She erupted, saying that she didn’t have time for that and that we needed to move quickly. When I was still too dumbstruck to speak, she lost her lid. She stormed out, screaming at me.
I got a call from the woman that set us up asking what happened and why the woman was “heartbroken.” I tried to explain, but I’m not sure she really believed me.
24. About As Deep As A Puddle
I had a prom date back in high school that irked me. We were set up by our friends. We met up at a Starbucks before prom to get to know each other. He only ever asked me questions about myself as a formality. No follow-ups. Stuff like: “So what do you like to do?” I’d reply, “Oh I do a lot of theater,” and all he would have to say back in “Cool, anyway…”
He was clearly not interested in knowing more about me or my interests. Prom went well enough though, and I ended up going out with him a few more times. I was 18, kind of desperate, and he was hot—what can I say? So yeah, it worked out…until I realized I literally couldn’t stand it anymore.
25. Back To The Pond
I met a girl on Plenty of Fish over a decade ago. The first time we talked on the phone, she called me while she was drunk from her ex’s house. She went on and on complaining about him and the fact that he talked to other girls. Somehow, I overlooked this red flag. I shouldn’t have. We agreed to get a drink the following day, but when I told her that I was running late getting home from work, she told me to just delete her number. I responded with: “You got it, Miss Cleo.”
26. Getting Ahead Of Yourself
This guy would hound me if I didn’t answer his calls. He’d be like: “Why didn’t you answer? What were you doing?” Dude, I don’t know! Working? Maybe doing literally nothing and I just didn’t want to talk to you?? One time, after not answering his messages, he demanded to FaceTime me. I should have ignored him, but sadly, I didn’t. On the call, he told me that he didn’t like my scarf and that I probably shouldn’t wear it anymore.
Did I mention that we’d only been on one or two dates? He lived out of town and he said he wanted to see me. I said we could meet at a hotel, which we did. It was a pretty nice place…but our hookup was utterly disastrous. When I was in the bathroom, he looked on my phone’s lock screen and read my texts.
My friend had texted me Merry Christmas, and my date wanted to know who it was and why we were talking. I felt so violated. I still get mad thinking about it, four years later.
27. Beauty Is In The Eye Of The Beholder
This is before I knew what a dating site was. Random girls would message me from my area on ICQ back in the day. I was probably 17 or 18. I met a girl on there who was very straightforward about wanting to get freaky. Now, I had retinoblastoma as a child and lost my left eye. I have a prosthetic, but nobody at my school really made a big deal about it, at least to my face.
I was treated like any other kid. I was naive to the fact that this could be seen as undesirable to a female. So, we talked quite a bit on there and she proposed we go for a drive; I assume so she could see if I looked attractive enough to hook up with later. It went okay, but because I was driving, she never really saw the left side of my face.
The next time, she proposed that I pick her up to go to my parents’ house and “watch a movie.” So, I picked her up and took her down to my room. I walked in and she stopped behind me in the doorway. I turned around and look at her. She was looking at me weirdly. “Your eyes aren’t the same color,” she told me. I said, “Yeah, I lost an eye as a kid, so one of them is fake.”
She thought I was joking and made fun of me. I forget what she said, but I wasn’t offended and I actually laughed. Then she said, “Oh my God, you’re serious…I’m so sorry!” She wouldn’t look me in the eyes and she said she was so embarrassed that I had to take her home right away. So I dropped her off and I never heard from her again.
28. I Remember You
This guy I was on a date with was going on and on about his ex, saying how she was the one that got away—but that’s not even the worst part. When he mentioned her name, my stomach dropped. She was my high school bully.
29. A Happy Accident
One time, I met a girl online, and for our first date, we went bowling after a cheap dinner. Well, as we were bowling, my dinner began to not sit well with me. I had to run to the bathroom. Before I could get my best first date jeans off, disaster struck. I proceed to poop myself a little bit. I was able to make a save for most of it, but I certainly got some on my pants and leg.
I was able to make a hasty cleanup operation in that bowling alley bathroom—enough so that I could proceed with the date without too much suspicion. I didn’t tell her this until more than a year after this date. Three months ago, we got married.
30. Moving At Light Speed
I had a girl tell me she thought she loved me about halfway through our first date. I brushed it off as flirty banter—but she wasn’t done with me. Toward the end of our meal, she said: “You know how I know you love me? You didn’t say that you didn’t love me when I said I loved you.”
31. Hiding In Plain Sight
I was out with my friends at a bar one evening. One friend in our group was particularly gorgeous and she got LOTS of attention while we were out. Three of the four of us went to get drinks, and our gorgeous friend was left by herself for a few minutes. This guy sidled up to her and started chatting her up. She was kind of giving him the side-eye, but he still prattled on.
We got our drinks and kept our distance to see what happens. At some point, there was a lull in the conversation. She looked at him, then at his hand, and delivered the most legendary line of all time. She told him: “Listen, the next time you try to pick someone up at a bar, at least take off your wedding ring first.” He felt his hand, felt the ring there, turned about ten shades of red, and just walked out of the bar.
What an idiot.
32. What’s My Line?
I dated a guy who, when we hit a lull in the conversation, would visibly think hard to see if there was another anecdote he could tell. Dude, just ask a question! I love hearing your stories but I am not just a repository for them!
33. Less Than Semi-Charmed Life
I messaged a girl online. She seemed a bit odd, but I thought I’d see where it would go. I picked her up to go to a movie or something—we hadn’t really planned what we were going to do—and when I got to her house, she was with her mother at the door, waiting. Her mother was bouncing up and down with excitement. It was obvious that she’d Photoshopped her pictures. Not necessarily a deal-breaker, but the dishonesty was greatly concerning.
She got in my car, which, at the time, was a banged-up five-year-old Mitsubishi Lancer…hardly a Ferrari. She said it was the nicest car she’d ever been in. Okay, again, not a dealbreaker, but a bit odd. As we drove to the city to grab a bite to eat, she started talking about Charmed, the TV show. I had never seen it and after 40 minutes of her talking about it, I decided I would never plan to. That was all she talked about.
I ended up bailing on the bite to eat and just took her on a walk around the city before driving her home. It was horribly awkward as there was absolutely no chemistry, plus she had a questionable body odor. I dropped her at her house, assumed she thought it went as badly as I did, and thought nothing more of it. Boy, was I wrong.
The next day, she called me while I was working…six whole times. I realized she was crazy, and after a couple of days of this, I messaged her to say that I didn’t think we’d really clicked. She messaged back and said it was the best date she’d ever been on and that she couldn’t believe I didn’t feel the same.
I apologized to her, saying I just didn’t feel it. I foolishly thought that would be the end of it. Wrong again. Over the next couple of months, she called almost every day. Fortunately, it eventually stopped. We didn’t go on a second date.
34. No Means Yes
I had a guy call me 20 minutes after a first date because he “just wanted to hear my voice” and he “missed me already.” This was already terrible—but it’s far more twisted than you think. This was after I had told him that I didn’t think it would work out and there wouldn’t be a second date.
35. My Resemblance Precedes Me
I attended freshman year at UNO. I had a relatively normal year, except most girls I encountered seemed to actively avoid me. I finally asked a classmate if it was all in my head. He said I looked a lot like some guy that crept on a lot of girls. He told me some rumors about what the guy did, blah blah blah. The next year, I transferred to another school.
I thought my ordeal was over, but it was just beginning. In the first week of classes, nearly everyone on the campus gave me a “doe in headlights” look. I find out the creeper attended the school too and he had a much worse reputation here. How do I find out? Campus security kept on getting calls about me “roaming the campus again.”
36. 20 Questions Minus 18
I had a guy ask about my exes and why we broke up so he could figure out what my “issues” were. He then asked if I was good at communicating and I said yes, I think I am…to which he replied, “Yeah, but that’s what my ex said too.” I never saw him again.
37. Loathe At First Sight
I met a girl online. We’d talked quite a bit via chat and telephone and things seemed to be going great. We had a lot in common, our senses of humor were pretty similar, she seemed really nice…I was pumped. For our first in-person date, we met at a Kaladi Bros coffee shop. She was already there waiting for me, so I walked over to her table and introduced myself. She looked me up and down and said: “Haha…no,” and walked out shaking her head.
38. Left Holding The Baby
I went to see a movie with a girl who I’d been talking to for a few weeks. During the flick, she started sucking her thumb like a baby. I was thinking, “It’s probably just a weird tic, but okay.” Halfway through, she got really emotional, dropped to the floor, and started rolling around like a toddler.
Then she got up and acted as nothing happened. I was 17 at the time and it’s the strangest date I’ve ever been on to this day.
39. Father Knows Worst
A girl from school had her friends tell me she liked me, so I made plans to go to the movies with her that weekend. My sister and her boyfriend were going to the movies as well and he had a truck, so he offered us to squeeze in and give us a ride. He took me to her house and her father answered the door. He was a jerk off the bat and started asking me a bunch of questions.
We went outside to get in the truck, and his reaction was terrifying. He came running out, screaming, “NO WAY! THERE’S NO WAY YOU’RE RIDING IN THERE!” It was really awkward. My sister said, “Well, we will go home, get my dad’s car, and then we’ll go.” He said okay, so we went back to my house and my dad offered us a ride.
We finally got to the movies and stood in line at our theater. Then I heard someone yelling her name. We turned around and it was her dad gesturing for her to go to him. She went over there and he started yelling at her, saying that he knew we didn’t go back and get the other car. After explaining for 15 minutes that my dad ended up giving us a ride, he still stood there.
He even watched us buy the tickets and walk inside before he left. I never asked her out again.
40. Not For The Faint Of Heart
I met her on OkCupid. She was really cool—she had short, dyed hair, and she worked as a fashion photographer. She was older than me—30 years old to my 20. We sent some messages to each other back and forth and eventually had our first date without any red flags. That said, she did seem to have the attention span of a goldfish. Turns out, she had chronic Lyme disease.
On the second date, she invited me to her house to watch a documentary about Lyme disease. Lots of things happened. I soon realized that she was actually a red flags wholesaler and I was on the warehouse tour. When I tried to leave at midnight, she had a panic attack and somehow guilt-tripped me into staying. I agreed to stay, hoping the night would come to a natural ending. It didn’t.
When I tried to leave again, she had another panic attack. She abused some painkillers in front of me and then tried to give me trinkets for about an hour. A couple of other uncomfortable things happened before I managed to leave the house. By that time, it was already noon the next day. There was another panic attack, but this time I was determined.
I started my drive home. I had gotten about 20 minutes of sleep in total. I was so exhausted I started crying while I was driving and I even had to pull over into a park to call some friends who talked me through it.
41. Do As I Say, Not As I Do
I dated a girl for about six months and she constantly talked about her ex. Apparently, they only broke up because he had to work in another part of the country. Occasionally she would be saying something about him that was relatable to my ex, and I’d be like oh yeah, my ex did that too. Her reaction was utterly ridiculous.
She’d tell me I need to let go of the past. In the end, we broke up and during that conversation, she said that I needed to move on from my ex.
42. A Lot To Unpack
I met this girl online and after texting for a few weeks, we decided to meet in person. We met at a museum in the city. The first thing I noticed was that he was wearing a fanny pack. In the front. Umm, okay. Then, he told me he was a federal agent…and he carried his weapon in the freaking fanny pack.
After the museum, we went back to his place where he seemed very awkward being in the same room with me. I tried to make him more comfortable, and that’s when he decided to blurt out that his mother had hung herself. Apparently, that’s why he wasn’t so comfortable with women.
43. Hit And Run
One time, a girl came to my place after a date. She went to the bathroom and spent a good amount of time in there. Then I heard three flushes. She left in a huge hurry, leaving me with the overflowing toilet after her giant dump. So awkward.
44. Let Them Eat Crab Cake
I went on a blind date with a man who started crying while he was ordering appetizers. He tried hiding behind the menu, but the waiter signaled to me that he was weeping. I pulled down the menu to reveal his tears. It turns out this was the first date after his divorce was finalized. I told him that I understood (I didn’t) and I sent him home with crab cakes (that I paid for).
He has since remarried and is happy. I haven’t returned to that restaurant.
45. Detective Dealbreaker On The Case
My first clue: he’s late. Second? He has alcohol on his breath and orders a drink as soon as we get to the restaurant—but he does this all the while scoping out other women and not looking at me. The first might be excused, but the second is a definite date dealbreaker.
46. Mutualism In Action
I dated a girl when I was in my early 20s. She had gotten married but for citizenship reasons. At some point, I met her husband and he approached me with a stink face. For a moment, I really thought that she’d lied and that I was in huge trouble. Then, he said, “I hear you’re the guy who’s been screwing my wife!” He threw his arms up and hugged me, yelling: “GLAD TO FINALLY MEET YOU! I’ve heard so much.” He was the friendliest guy and I’m still friends with both of those people to this day.
47. Time Is Money
This reminds me of a girl that I went on one date with. One day, around a week after our date, I mentioned that I’d forgotten my wallet, which was a bummer because I had to pay for parking. She offered to drive from her work to mine (which was a 45-minute drive) and she said she’d spot me $20. I said it was okay, I would just borrow from a colleague. She seemed to agree…but when I was done work, I was greeted by a chilling sight.
Guess who was waiting outside my office when I finished, several hours later? Apparently, she’d “only” been there for 90 minutes.
48. Table For Two—Plus One
I went to a restaurant with a guy I met online. He seemed like a really good guy and we actually hit it off really well. We were sharing a dessert and having a nice time…until some girl came over and dumped a drink all over him. At first, I was furious at her, but then she started screaming and the shocking truth about him came out. She went on about how she loved him and how she couldn’t believe he’d gone behind her back.
She was out to dinner with her mother at the same restaurant. Apparently, their plans had changed and he had no clue she would even be in town. He left me at the table, running out after her and her mother, who was screaming profanities at me from across the restaurant. I was nearly in tears trying to explain to the waiter—and really anyone who would listen—they had made quite a scene. I had NO idea that he was engaged.
Then, because he had left, I got stuck with the bill—but there was a twist. After the whole incident, he tried to go out with me again.
49. The Worst Of The Worst
I dated a girl I met online. She was a CNA (certified nursing assistant) who provided home healthcare for terminal cancer patients, She would go to people’s houses and help them eat, bathe, pay their bills, and so on. She would also help those who were nearing the end of their lives to be as comfortable as possible during their last moments. Based on her job, she seemed like a formidable woman…but then I started dating her.
That’s when I learned her absolutely horrific secret. I found out that she was stealing from her clients; dying people. She’d literally watch them die and then take what was theirs. She would help them pay bills and try to comfort them in their financial distress; all while stealing their money from under their noses.
I asked her why she would do this. I gave her money all the time and she lived with her dad, so she really only had her phone bill to worry about. She said she wanted to be a strong person, and I guess preying on the weak somehow made her feel strong. I dropped her and reported her to her employer. They did nothing and local law enforcement wasn’t interested in an ex-boyfriend’s words.
Last I heard, she’s still a CNA; though now she looks like garbage.
50. Chef’s Special
I met a guy who said he wanted to make me dinner. 19-year-old me thought this was a sweet idea. When we got to his house, I had to pee. I used his bathroom and when I came out, he was naked on the couch. I’ll never forget what happened next. He looked at me and said: “Dinner’s served!” I told him I wasn’t hungry anymore and left.