First Dates Gone Wrong

May 8, 2023 | Rachelle Horne

First Dates Gone Wrong

Everyone has experienced at least one bad date in their lives. From cringe-inducing creeps to full-fledged psychopaths, you never know who the person sitting across from you will turn into by the end of the night. The following Redditors shared their stories of bad first dates and they're so horrible, they'll make you want to stay single. Read on for some messy tales:

1. 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.

first dates gone wrong

2. 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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3. 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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4. 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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5. Mutual Attraction

I went to pick up my blind date. She opened the door, looked at me, and said, "Ew". I'm not sure what prompted me to reply this way, but I just looked at her and said, "Yeah, I agree". I then turned on my heel and left. The entire date ran for less than five minutes.

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6. Dodged That One

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 detail, how he threw 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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7. 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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8. The Den

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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9. Judgmental

I had to pick him up and he complained about car, the way I drove, my music tastes, why I was being so quiet, etc. But the moment that definitely did it was when he said, “My friends really want to meet you. I need them to know you’re real". That’s when I bounced.

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10. Not A Family Guy

He 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.

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11. 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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12. My Crazy Ex-Boyfriend

To start our date, we 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.

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13. I Spy

We 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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14. 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.

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15. 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 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.

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16. Thanks But No Thanks

We started chatting online. At the time, I was a smoker and I told him this. He said it was no big deal because he smoked too. One day, we decided to meet up at Starbucks for coffee. The first thing he said was: "Hi. By the way, when I said I smoke, I was talking about the hard stuff". I said, "Oh. Bye!" then turned around and left.

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17. Double Date

She looked over my shoulder and said, “Oh, my other date is here".

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18. 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 chest. Even the people two tables over just stopped and looked at him.

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19. Pet Peeve

She brought her pet rat with her. It was hanging out in her bra and she fed it French fries. She also casually mentioned she had warrants, so I just faked an emergency and bailed.

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20. 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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21. Netflix And No Chill

She 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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22. Uncontrollable Urge

He 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.

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23. Stalker

It seemed to be going alright for a while. 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 truth—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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24. 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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25. Don’t Cross Streams

I went out on a blind date. She took me to a strange party and asked me if I wanted to go #1 on a guy with her. I told her, “No thanks, I’ll use the urinal this time,” then split.

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26. 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.

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27. Mute Date

He wouldn’t really talk. I tried asking him a couple of questions, but he just sat there staring at me. I finally gathered the courage to get up and leave after about 20 minutes. I’m glad we were just at a local Timmy’s, so it was easy to take off.

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28. Not In Your Future

She 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.

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29. 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.

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30. 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.

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31. 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.

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32. Stay Inside

I went on a first virtual date during the lockdown and this girl went off on a whole thing about how having an outdoor cat is bad for the environment. No matter how a topic began, it always wound up back right there, and that was the one that broke me.

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33. 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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34. Chivalry Is Gone

I drove us 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.

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35. 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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36. Merry Christmas Rusty

The first red flag 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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37. Don’t Be Stingy

She demanded free food when the kitchen didn't put ketchup on her burger at a sit-down restaurant. That's it. They just forgot the ketchup and she acted as if it was the end of the world.

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38. Your Insecurities Are Showing

She 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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39. 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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40. 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.

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41. 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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42. Won’t You Be My Neighbor

I didn't even realize it was a date. 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 huge revelation 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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43. 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.

Bottled-Up SecretsShutterstock

44. 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 immediately regretted 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".

Cheaters ExposedShutterstock

45. 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.

Horrific Blind DatesShutterstock

46. 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 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

47. 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.

Co-Worker KarensShutterstock

48. 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.

Weirdest Date FactsShutterstock

49. Beyond Inappropriate

I met a guy through an 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 most chilling 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

50. 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

Sources: Reddit


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