"Check, Please!": These Dates Turned Creepy In An Instant

February 10, 2021 | Scott Mazza

"Check, Please!": These Dates Turned Creepy In An Instant

We’ve all been there: the date is going well, or at least not horrifically. The person across from us seems kind, funny, or even normal—and then, all of a sudden, he or she says something incredibly creepy, and everything unravels with that one sentence. These Redditors have been in that nightmare and lived to tell the tale. 

1. Make Up Your Mind

We met at his house before he took me out to a "surprise" lunch that he planned. It turned out he just drove us to a McDonald’s. But it got so much worse from there. He turned to me and said, “By the way, I invited my ex to join us for lunch.” I would have left before she got there, but since he took me in his car and taking a taxi back to his house to get my car would have been expensive, I stayed.

The ex was actually really nice and tried to make things less awkward. She didn’t know it was a date; she thought she was just meeting with her ex for lunch. She was just as shocked as I was.  While my date was in the bathroom, the ex confided in me that she was hoping they would get back together. I told her that it was fine because I had no interest whatsoever at that point. 

After lunch, he took me back to his house and the ex came too. He tried to put a movie on but I insisted on leaving. His response was mind-boggling. Despite the fact that he clearly didn’t want me, he took my car keys off the bench and locked himself in his bedroom while he hid them from me. His housemate had to help me find my keys.

He later started the movie with his ex and I left without saying anything more. There was no second date and those two ended up back together a few weeks later.

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2. I Was Rooting For You

“Look, this has to go well. Both of my brothers’ wives are pregnant with their second children. Do not let me down.” He said that to me within three minutes of sitting down. I thought it was a joke at first and tried to awkwardly laugh it off, but the tone of his voice was something I’d never heard before. He also didn’t blink much and he had the most intense, intimidating stare.

It was like he was trying to make me break down and confess my darkest secrets right there at the table. Some other things were said, mainly pertaining to his occupation, that made the hairs on the back of my neck stand up. Looking back now, I feel like there’s a 99% chance he was doing unlawful stuff at his job, and whatever he was doing would have impacted a ton of people for life.

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3. Card-Carrying Monster

It was a horrible date. This guy was incredibly misogynistic, talking bad about his ex-wife and saying that most women are bad mothers. He was saying why he doesn't date within his old-school, Romanian gypsy community is because the women lay like fish during intimacy. He even went as far as to say that he thought American women were more fun in the sack.  

I know, I know…I clearly didn't vet him enough before hanging out with him. But then he outdid even himself. He took my credit card out of my purse when I wasn’t looking. Luckily, on the way home, I stopped for coffee and noticed it was missing. I froze the account that very second and searched everywhere for three days, hoping I was wrong. 

But I knew deep down that I had been played. I just got that gut feeling. I never did find that card. 

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4. A Song In The Key Of YIKES

I told this guy I played the piano, and half an hour into the date, he said: "If I wanted you to always remember me, I'd break your ring fingers. You know, 'cause they don't heal well and then you'd always think of me when playing." Suffice it to say, I left the restaurant fairly quickly after that and never returned his (numerous) calls from then on.

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5. Nightmare In Paris

I went on a rollercoaster of a date with a French guy in Paris. It was summer and we were meeting on the steps of Sacré Cœur. We arrived and he brought a bottle of red. I then jokingly said, “Oh you got red...in the summer!” He responded with, “Oh, I guess I’m trash for getting the wrong kind." After he said that, I immediately knew I had made a dire mistake. 

I reassured him and told him I was just teasing. During our conversation, he kept complimenting me incessantly. Like to the point where I got uncomfortable. After like 10 compliments, I didn't even know what to say anymore. At one point, I was telling him a story and he kept interrupting me to say, "Your eyes are so beautiful; I can't stop staring at them." 

I was like, "Thank you, that is so nice...Okay, back to my story." It was nonstop. After the 19th compliment, I heard him mumble in French "...And I'm waiting for you to say the same to me..." I spoke up and asked, "What was what?" And he replied, “Oh nothing.” Apparently, he didn't think I spoke French, but I am actually fluent. 

So THAT was uncomfortable...shoving compliments at me and pouting when I didn't give him one back. Like sir, if I wanted to compliment you I would—I love complimenting people, but I wasn't overly attracted to him. Red flag number two. He asked me if I'd been on many Bumble dates to which I said yes, many. 

I'd been single for a while and so I went on dates often. He didn't like this. He began asking me why I hadn't settled down with any of my past flings, and I explained that I'd met lots of really great guys but it just never clicked. He then got weirdly quiet for a few minutes before saying, "You know, not everyone is going to be as perfect as you...Life isn't a fairy tale...You have to give people chances, you know."

At that point, I realized I was seated next to a French incel or one in the making. I replied that I never thought I was perfect or better than anyone, and stressed the point once again that I hadn't settled down because there hadn't been a strong connection yet—NOT because I was not giving these guys chances. 

I explained that dating is a two-person thing and sometimes the guy didn't want to meet again also. That was red flag number three. At one point on the steps, he started asking me where I lived and I said, "Oh, just down there like two streets down." He then kept asking me to be more specific, insisting that I tell him which street... Jesus Christ. 

Oh, and there were a lot more self-deprecating sentences sprinkled throughout his conversation. At that point, I was just trying to get out of there as soon as possible. As we walked up the steps to the top, I started planning my exit. As I was about to leave, he looked at me and said: "You HAVE to give me another chance." 

I replied, “Listen, thank you for the bottle of red, but I am not going to see you again, I'm sorry.” He then got very upset. His eyes got huge and he started yelling. "I'm educated, I have a CDI... you must give me a second chance." In France, a CDI is a permanent contract and it's a big deal because you can't be fired. Then again, every person I know has a CDI. 

And since when does having a permanent contract equate to women owing you something? By now, people were starting to look at us. I kept calmly telling him that no, and at some point, he lost it. He GRABBED my arm while continuing to rant about his CDI. When he noticed that people were looking, he let go.

There was one moment where he got so mad I really thought he was going to hit me. I could see him thinking about how to keep me there without causing a scene, and I just took my chances and ran down the stairs as fast as I could. I was obviously terrified because he now knew the general area where I lived...Thankfully, he didn't follow me. I never blocked someone so fast in my life.

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6. The Boy Is Mine

While she was driving us back home from the restaurant, she started saying things like, "You know, you're in my car now, so I technically can take you wherever I want. You're like my captive.” I laughed the first time she mentioned it because I'm into dark humor, but when she kept going on with it, it started to really give me the creeps.

Little did she know that once I got out of the car, that would be the last time she'd ever see me.

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7. Mother Knows Best

It wasn’t my date who was creepy, but his mom. It was 1992, I’d barely turned 17, and I just had my first “kiss” that summer during a game of spin the bottle. At school, I noticed we had a new student in the class. He went up to me and said he thought I was cute. He gave me a ride home from school and then asked me out to a movie that weekend.

During the whole movie, he was all over me—lots of attempted kissing. After the movie, he wanted to park at a secluded section of the highway to “talk”. I quickly vetoed that idea. I may have been inexperienced, but I wasn’t dumb or naive. Instead, I suggested heading to the local family restaurant that my mom worked at; though she wasn’t working there that day.

Well, we ended up running into his parents while we were there. We chatted for a few minutes and then his mom leaned forward, took my hand, and said, “You know dear, we’re not going to be home for several hours if you want to go back to our house for some private time.” At that point, I developed my first migraine and had the boy take me right home. I did not date again for the rest of my senior year.

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8. Oh, Baby

On our very first date, she showed me a long list on her phone of at least 60 to 70 baby names for her future children. She joked about having baby fever constantly…but it was obviously not a joke. Weirdest and maybe worst of all, they were all really country-bumpkin names like "Brekken" and "Gatlin", which somehow made it more unpalatable for me. We were both 21 years old. 

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9. More Than A Little Off

One of my co-workers went on a date with a guy who worked with us. We had all been friendly with each other, so she told me that they were planning a date that night. To be honest, the guy creeped me out. She was 16, and he told everyone that he was 27 although he was actually 32 or so. But the creepy age gap was not the only thing on my mind.

He would say crazy things at random times. For the first month or so, it was mundane but normal. Toward the middle of the second month or so, he would just slip random thoughts into the conversation. He would say stuff like how he wished leprechauns were real so he could skin one, or that you could freeze a banana, stab someone with it and then just eat the weapon. That’s what we were dealing with.

We worked in a grocery store, so we'd often make conversation with each other. At one point, he'd be telling me about something mundane like the weather, his plans for the weekend, etc. Then, mid-sentence, he would pick up a box of Trix cereal and say, “I’d drown that rabbit in the milk and crunch his bones with that cereal” before putting it back on the shelf. 

He once had to change the receipt roll, and in the middle of doing so, he told me that he could probably crush a cat’s skull with it. Honestly, the complete switch in what he was saying and how he was saying it was significantly more disconcerting than what he was actually saying. I had talked to the store managers about my concerns, but this was quite a while ago and nobody cared.

Anyway, I tried telling the girl who was going to go on a date with him that he was crazy dangerous. She told me later that she thought I was making things up because I wanted to date him myself. A few days or so later, she showed up and my jaw dropped. There were bruises on her hands, a couple of her fingers were taped together, and she was very obviously wearing heavy makeup.

Apparently, he had experienced some sort of episode. After picking her up, he proceeded to head straight out of town instead of to the center of town where they were supposed to be going. When she asked where they were going, he told her, “We’re going to the bridge because I need to finish you.” She tried getting out and he began beating her, screaming that they needed to get to the bridge.

After a couple of rounds of this, she escaped his car and he took off. The authorities were called, reports were filed, but the guy just vanished. When I lost contact with her a year or so later and she went off to college, he still hadn’t been found.

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10. Do You Want To Play A Game?

I went out with a girl one night and after dinner, she drove me up into the mountains. Since I was new to the area, she wanted to show me around town. After a while, when there were no more lights, she started talking about…serial killers. I still remember her saying, “I used to think about getting away with stuff like that sometimes.” Uh…yeah, I didn’t go out with her again. 

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11. Fate Works In Mysterious Ways

I was living in Germany and had a date lined up with a German woman. We met at a restaurant, and within five minutes of sitting down, she said, "We really need to work on your German, but that's okay, we've got our whole lives together for that." First red flag. A few minutes after that, she started talking about her son, explaining that he lived with her parents because the court ordered it. 

We hadn't even discussed the restaurant menu yet, and this gal was dropping this kind of information. Second red flag. On the topic of her son, she decided to dive into the colorful history of the father. Basically, he knocked her up six years prior and rolled out. Mind you, I'd spoken about five sentences by that point because she was not giving me a chance to speak.

Suddenly, her phone rang and she answered it...at the table...in a really nice restaurant, less than 10 minutes into the date. She pulled the phone down and said to me, "I really need to take this call." We still hadn't ordered our food and I was just sitting there, by myself. Five minutes passed....10......20.....and then I finally ordered my food.

I got my food, ate it, and prepared to pay the bill. I assumed the girl wasn't interested and just ghosted me—NOPE! After an hour, she came walking back to the table, crying her eyes out, saying that the call was from her baby daddy. He allegedly wanted to get back with her. She was upset because it was a tough decision. She really loved him but was also excited about a future with me.

At that point, I finally had enough and said it would probably be best if we didn't talk again. I paid the bill, then left. After leaving the restaurant, she texted me at least every five minutes. It ranged from saying sorry to things like, "How could you do this to us? We were supposed to have such a good life together!" I ended up having to change my number because this went on for a week.

Here's the good news: I swore that I was done dating for a while after this incident, but then I ran into a girl who was interested in dating me two weeks later and I gave it another shot. That was my last first date—we've been married for nine years now.

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12. What A Catch

I went on a Tinder date to the movies when I was 18. He picked me up in his truck and played terribly loud, depressing music. In the theater, he was on his phone swiping on Tinder the whole time, then, at some point, he leaned over and told me that I was lucky to be out with him because all these other girls wanted to be with him. YIKES. My roommate picked me up when I excused myself to the bathroom.

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13. A Surprise In-Store

We went on an early evening coffee date and it was going pretty well, so we grabbed dinner together afterward. Towards the end of it, he said, "You know, I could break your heart so easily. I could absolutely destroy you. I could make you fall in love with me and then just...Disappear." I laughed uncomfortably, but the conversation basically petered out after that. 

When we finished eating, he asked if he could see me again. I said, "Uh, you know... Maybe...." And then got my butt outta there. Also, at one point, he asked me for some "sugar" (a kiss) while we were chatting in his car, to which I firmly said no. He then replied, "I guess some girls are pretty and like to be called smart, and some are smart and like to be called pretty. Which are you?"

There were so many things wrong with his attitude. Looking back, I can't believe I stayed out so long, but I guess the weirdness didn't start until after we got dinner. I kept just thinking maybe he had an odd sense of humor until he dropped the "destroy you" line. After that, I was out.

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14. Daddy Issues

“My son is gonna love having you around.” Lady, we talked twice on Tinder and I’ve only known you for five minutes. Ease up on the step-daddy talk. Full disclosure, not long after this ill-fated date, I met a nice woman on Tinder who also happened to have three children. I adopted all three not long after we married. So, yeah. 

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15. Pillow Talk

This guy wasn't talking at all. I only brought a few talking points with me because normally guys tend to talk the whole time. I didn't have anything else to say, so I asked him to start talking. He replied, “What I want to talk about can't be said in public." When I ended the date, he thought we were going to go to my place to "talk" some more, but I told him no.

I got in my car, noted what car he got into, and took a few breaths to calm down. I looked around and his car was still there. I waited 30 minutes before he left the parking lot and stayed another 15 minutes before I left, just to be sure he was really gone.

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16. Mrs. Dressup

On our first date, we went back to her place. While giving me the tour, she pulled a beautiful wedding dress out of a closet and said, “When we get married, I can wear this dress,” while holding it up to her body. To be completely honest, I didn’t react that well...I just said, “Aww, put it on and I can take it off.” Then I never called her again. But that’s not the end of the story. 

Three weeks later, she called me at midnight to tell me; “I know you have people watching me. I can't go to work or school with your people sitting across the street all day and night.” It actually made me feel worse about my decision to sleep with her since she clearly needed help, but it also confirmed my suspicions about her overall vibe. 

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17. True Romantic

This dude and I kept randomly being on the same bus. We would never talk, but sometimes we'd make eye contact. After a few months in this cycle, we got off at the main bus hub. He approached me and asked me to dinner. There was a teriyaki place right across the street, so we went there and had a good conversation. I had a good time…until it came to the end of the date.

When the time came to separate ways, he brought up his hand and cupped my cheek. He just sort of left it there in silence...then slowly grazed his fingers down along my face as he pulled away. I did not call him. 

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18. Photo Finish

This was in the early '00s when I agreed to go on a date with a persistent co-worker at Target. He showed up at my house with a giant bouquet of flowers. My parents invited him in to check him out and they spoke with him for a bit. It started to get strange at that point. Everything he was saying about his background didn’t really check out—he said he was a volunteer firefighter in a year when he would’ve been like 10 years old. 

Then, all of a sudden, he pulled out a disposable camera. When my mom asked him what it was for, he said, “Your daughter is going on vacation for a week and I want a picture to remember her by.” Then, like from a dark comedy, we heard the click of the shutter. I faked being suddenly sick and my mom told him I wasn’t feeling well. Luckily, it was only a summer job, so I didn't have to see him after that.

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19. Straight Out Of A Movie

He insisted he drive me to the movie theater, which meant he would have to drive to my town 45 minutes away, then back to his town to go to the cinema, then back to my town to drop me off. I told him I was fully capable of driving myself to save the multiple trips. When I adamantly refused a ride, he still drove to my town, bought me a coffee, and insisted I go in his car. 

I still said no, citing the fact that it would be dangerous for me to get into a vehicle with a person I didn’t know, and I drove myself to the cinema where I had a friend meet me for the movie. The guy still came with us and even paid for me despite me telling him that I didn’t think it was a good idea. I never spoke to him again and blocked his number.

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20. Animal Instincts 

He described at length how men were all naturally as violent as the men in the movie A Clockwork Orange. He explained that they actively suppress their rages in order to fit in with society...He also invited me to a pub and proceeded to drink water while buying me seemingly bottomless G&Ts. Needless to say, I yeeted out of there real quick.

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21. Mr. Big

My mom was an online dating pioneer. She was really interested in finding “someone special." She agreed to meet this one guy for dinner (first mistake) and she went in to be seated prior to him arriving. When he came in, the waitress brought the menus. He set down his menu, and the first words he spoke to my mom were horrific.

He asked her if she knew anyone who had an enlargement surgery, uh, down there. He then went on to explain that he had flown cross-country for this operation and that it had “gone wrong.” He went into great specifics about just how wrong, too. My mother excused herself to the ladies' room and went out the back door. We still laugh out loud when she tells us that story.

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22. No Means No

It wasn’t a date, but he’d convinced himself it was. It was just a mutual commiseration over the two of us not getting to go on a company trip. We were at a bar near the shop and coincidently, it was near his house too, so I parked there to avoid paid parking. When I got out of my car, he asked me to come inside to “pre-game” and I got weird vibes.

I’d turned him down twice before and something about the scenario flicked on a switch. I lied and said I’d rather have only one drink at the bar as I was going to drive home later. He then said, “Oh! I’ve got sealed drinks in the fridge and my roommates are home, don’t worry.” After he said that, I got EXTRA worried. Now, I’ll admit to being a pretty paranoid person. I went to school to be an officer and am an insufferable party mom. 

I don’t drink booze out of open spirit bottles. I also don’t go into other people’s homes without at least one other close friend with me. Both are rules that were born out of necessity from experience. I’ll admit the odds were stacked against him on that one.

The thing that first set me off, though, was the offer to come inside. I’d already turned down his advances twice before and he was proving himself to be disrespectful of my boundaries. He was super awkward, however, so I was willing to give friendship a chance. That's why I even considered going to the bar with him in the first place. 

I had no idea at the time that anyone else was home, and it was too intimate an offer to be sure he’d be respectful of my space in his own home. The nail in the coffin was when told him I just wanted one drink at the bar—he simply responded with another push about the “sealed drinks.” It just affirmed to me that yeah, he couldn’t take no for an answer, and I was pretty sure he didn’t intend to leave after we went inside.

One day after this incident, we were all on a bus heading to a meeting and he sat next to me even though I told him there were plenty of other seats. I stared out the window and ignored him the whole time. When we arrived, he asked me how my nap was. I said I wasn’t sleeping and he said, “No, I can tell when you’re sleeping.”

For what it’s worth, he was attractive. Probably an 8/10. I just wasn’t interested like that. Before I turned him down the second time, I actually liked him a lot. The first time I was clear and said no, but we just carried on as we were. The second rejection was a “Dude I already said no, this time listen to me because I mean it.” Apparently, that wasn’t good enough.

I quit shortly after the bus incident because my boss refused to separate us or do anything about it. 

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23. Constant Vigilance 

This was a distinctly creepy date I had. My first Tinder match got me to sneak out of my house at midnight. He led us into the hills and at one point he said, “What would you do if something attacked us?” He just stared right at me. Keep in mind it was a cold October night and I was in a sweater, sandals, and I had no weapon to defend myself. 

I can’t remember what I said back, but he then laughed and started talking more about different scenarios like running out of gas or getting attacked by different animals along the way. He then mentioned he had a katana in his trunk, and at that point, I really wanted to go the heck home. Needless to say, I never went out with him again.

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24. What Lies Beneath

This was 17 years ago and I’ll never forget it. I was 18 and worked with this guy who was 22. We worked at a big home loan company, and he asked me out for dinner after work one night. We were both working overtime that night until about 7 pm and I was hungry, so I agreed. I had interacted with him enough at work to feel comfortable getting into his car. I regretted it almost instantly. 

Instead of driving to the restaurant, he said he wanted his mom to meet me. He drove to his house on a farm that was 45 minutes away. We got there and he introduced me to his mom, but guess what—she could care less. Then, he gave me a tour of his place in the dark, showing me where they kept the pigs, the horses, and the rest of the animals.

I was uncomfortable at this point, but also naive and 18, so I made some small talk: “It must have been so cool to grow up out here. I would have loved this as a kid!” He then said something like, “Yeah it was, but I had a problem.” He then folded his arms and refused to make eye contact with me. Me being young and still naive, I asked him what he meant. 

That's when he told me a terrifying confession. He said he was a very angry teenager and that he used to kill the rats and mice on the farm. I then replied, “Oh, you mean like with a BB gun? That’s not a big deal.” Nope, not that. He told me that he used to trap them and then stab them while they were in the traps with his pocketknife.

Then he said his “problem” progressed and that he “ended up” stabbing the neighbors’ cat. Apparently, it got so bad that he did it to one of his own pigs. His mom found the pig and that’s when he knew he had to stop the behavior. At that point, I was majorly disturbed and wanted to leave. I was starting to realize that everything he was telling me was a “psycho in the making” kind of behavior. 

I reassured him that his problem wasn’t that weir” and that I wouldn’t tell anyone about what he had said. I started to get really hungry and wanted to get back to my car at work before they closed the gates. It was a big office building complex that shut its gates at 9 pm. So he drove us back and we ate dinner at a popular burger place as per my request. 

Afterward, he took me to my car in the empty parking lot at work. As soon as he pulled up, I thanked him for dinner and quickly got out of his car. I rushed into my car before he could even get out a goodbye. I never went out with him again. I tried my best to avoid him at work without being rude or making him angry, and luckily he got promoted to a different department in another building a couple of weeks later.

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25. Baby Mama Drama

He told me I was getting old and needed to get married so I could have kids and my grandparents could meet them. At that point, I was 25 and he was 24. The entire conversation was him waving a lot of red flags about wanting a baby mama and partner who “hadn’t gotten around.” Needless to say, there was no second date. Gross.

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26. The High Life

I once agreed to go on a date with one of my stepdad's clients, who was the son of a very rich luxury yacht builder in the country. The company is known for its extremely strict rules, particularly for women, some of which border on human rights violations. He took me bowling and rented out the alleys on either side of us as well so we'd have some privacy.

He was telling me about the lessons he'd learned from someone who'd coached several world champions in bowling. Afterward, he showed me pictures of his house—his bedroom alone was the size of a swimming pool, and his garden was a literal zoo with several monkey species as pets. He then started telling me a bit about his family.

He gave me a few little interesting details about each of them, and then it took a dark turn. He got to his older brother's wife, and it was pretty clear she was the main subject of the conversation. He told me his brother had studied in the UK as he did, met a nice English girl like me (even though I'm Irish, not English), and fallen in love. 

His brother had taken her back to his home and asked her to marry him, but with the condition that she move into his parents' house with him and live by their strict rules. She was reluctant at first but eventually agreed to it. Then he went on to say: "And her life there is so good that she never even wants to leave the house! She stays home and has babies and wears Prada and looks at the horses. She's so happy.”

He ended with, “Who would ever even want to leave a house like my family's house?" He started asking me if I'd ever like to go there and meet his family. Alarm bells were going off at a rapid rate in my head. When I got home and told my stepdad, he immediately took the guy off his client list and we haven't seen him since.

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27. The Eye Of The Beholder 

I was about 17 or 18 years old when this happened. We watched a movie together at the cinema. Afterward, in the parking lot, he licked my eye. LICKED MY EYE! Then he became all weird and possessive because he couldn’t get the hint that I didn’t like him. He kept texting me at 2 am to ask if I was at work (I worked in a small rest stop area in the middle of nowhere and had to be at work around 3 am on most days). He also kept demanding that I tell him where I was at all times. 

I eventually told him to go screw himself. I quit responding to him entirely.

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28. Take A Hint, Buddy

A few months ago, I matched with a guy on Tinder. Things seemed to be going well over chat so we ended up meeting for a date. As soon as we met, I had a bad feeling about him. I just had a vibe we weren't going to progress any further. He seemed a bit off and not as friendly as he appeared online. Still, I thought I might as well have a meal and chalk it down to experience if it didn’t pan out.

During the course of the meal, alarm bells began to go off. He started referring to women as "stupid and pointless" and "only good for one thing." I began to get really uncomfortable and was trying to think of a good excuse to leave. Of course, I got naturally defensive and said talking about women like that was derogatory.

He then started to complain that there were vegetables in his burger—referring to the lettuce—and he proceeded to pick it out. He called the waitress who took our order a “dumb witch” because he specifically said no vegetables in his meal. I finally said that I had to go because, honestly, at that point, I felt like shoving the lettuce in his fat misogynist face. 

To say I ran as fast I could to my car is an understatement. As soon as I got in my car, I ended up un-matching from him and I blocked his cell phone number. Later on, I still received a chilling text from another number. He said, "Hey, it's Brad from Tinder. I know pretty much all I need to know about you, so let’s sleep together, okay?"

Like, what the heck. It sounded so creepy; like he was analyzing me to see if I was suitable to sleep with. Also, he obviously knew I blocked him, so why bother sending anything at all? I didn't reply to him, obviously, and I blocked that number.

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29. Come Over To The Dark Side

My mom, who is a practicing Protestant, went on a blind date once sometime before she met my dad. The guy she was set up with claimed to be a Satanist. Not an edgy atheist with extra steps, but ultimately a harmless Satanist...I’m talking about someone who legitimately worships the devil. Yeah, that date went about as well as could be expected.

Oh, and the best part? The guy was faking being a devil-worshipper. Apparently, he thought it would somehow impress her.

Creepy DatesShutterstock

30. Just My Type

She told me that she was not desperate and did not necessarily want a boyfriend. She then listed a bunch of people who she had dated. At some point, she started to tell me that she has now lowered her standards and that she didn't care if her next boyfriend was tall, short, fat, thin, or even red-haired. I am short, fat, and red-haired. 

Creepy DatesShutterstock

31. Won’t Somebody Think Of The Children?

I got catfished by the craziest woman I've ever met. I don’t mean like, “Ohh, that woman is crazy,” I mean, every time she reached into her bag, I thought she was about to pull a weapon out by the way she was frantically rummaging through it. She seemed off from the jump from the moment we met. At one point, she looked at me and said, "Do you ever wonder what your kids will look like?" 

I replied, "I already know. My daughter is right there and she's perfect." The crazy lady continued, "No, I meant our kids, since we are going to get married and have a house in Texas." I had literally just matched with her on Tinder the day prior. We never once spoke of anything more than normal conversation topics on the app. Nothing in the slightest related to either topic. 

I faked a phone call from work, got in uniform, and told her she needed to leave. I waited for her to leave, then drove around the block.

Creepy DatesShutterstock

32. Jekyll And Hyde 

A guy I went on a date with had super scary road rage when he was driving us to a restaurant. I mean veins bulging in his neck, spittle flying; the works. He kept RAGE screaming as I clung to the door handle to get as far away from him as I could get. I kept wondering if he was going to pull out a gun and shoot someone, while also mentally debating if I should jump out of the car at the speed we were going. 

Then, at the restaurant, he was pure Mr. Charming; all concerned about why I was suddenly so quiet.

Creepy DatesShutterstock

33. I Put A Spell On You

"Gerard Butler mustn't find out about this. He gets very angry about my affairs." Not exactly a date, but she told me this while we were hitting it off at a party. She then explained to me how she married him (Gerard Butler) through witchcraft and showed me her "Book of Shadows," which was actually just a purple file folder with some badly drawn runes on it.

Creepy DatesShutterstock

34. Kiss Kiss, Bang Bang

He showed me pictures of his kids. "Here is Tommy, and the other one is my fat kid." I thought I misunderstood and made him repeat. Indeed, he called the other boy "his fat kid"...after I heard that, I told him I had to go. He insisted on taking me to my car, and while walking, he asked me, "How are you in bed?" I stopped in my tracks and had a good look at him.

I was 45 then, which is the prime age for a lady. To be honest, I felt like a million dollars. I felt beautiful. He was much older than what he had told me beforehand, and his prime happened 30 years ago. He was weathered with a bad haircut and he smelled bad. He was also so, so bitter with life. I simply replied that he would never find out.

As I was opening the door of my car, he tried to kiss me, but since I was taller than him, he kissed my shoulder. I closed the door on him and started the car—which is when the cherry on top happened. He put his lips on my windshield to kiss it. Imagine a grown man doing this, with a big smack sound. I was sitting in my car watching this happen, and his eyes were trying so desperately to be sexy.

My hands were on the steering wheel, touching the wipers/washer thing, and I played with the idea of splashing him for few seconds. I remember my finger touching the control...but I ended up not doing it. I actually felt pity for him. In the end, I had a funny story to tell, but he had a very embarrassing one to take home with him.

Creepy DatesShutterstock

35. Stirring Things Up

One time, I was the creep. I went out for drinks and tacos with a sweet guy from Tinder. It was going pretty well, so when he asked if I wanted to walk home and hang with his roommates, I happily obliged. When we arrived, his roomies were drinking screwdrivers. They asked if I wanted a glass—I said sure, but the thing is, I have a strange compulsion to stir any mixed drink thoroughly every time.

I couldn't drink from the cup until it was stirred. I walked into the dimly-lit kitchen and grabbed the first utensil I saw on the drying rack, which happened to be a steak knife. Walking back to the living room, everyone was looking at me like I had turned into a ghost. They straight-up thought I was going to slay everyone in the house with a steak knife until I started stirring my drink. 

Creepy DatesShutterstock

36. Poking Holes In That Dream

I went out with a girl I met through OkCupid once. She was a student in a nearby city, so I drove out there and we went on a very lackluster date. At the end, she invited me back to her place, and I accepted. When we got there, we ran into her roommate as she was leaving. The roomie told us to have fun and that she wouldn’t be back for a while. 

I went into the girl’s room and we chatted a bit. Then, things quickly turned intimate. Somehow, she segued into her telling me how she and her friend once went into the campus’ physical wellness center and used a needle to poke holes in all the rubbers they had set out when no one was looking. She told the incident to me like it was supposed to be a funny story. 

Afterward, she said she was going to run to the bathroom to get some condoms so we could get to business. Needless to say, we did not get it on that day. I told her something came up while she was on the toilet and left. Obviously, I never saw her again.

Creepy DatesShutterstock

37. Easy There, Rider

This is a Tinder first date story: I knew early on from the conversation that this guy wasn't going to be "the one," but he was safe and the sushi was good. At some point, he got into how he loved going on road trips on his motorcycle. I mentioned that I liked road trips too, just to keep up with the conversation.

Date: We should get you a motorcycle soon then!

Me: Uh-huh.

Date: Yeah, and we can get those helmet radios so we can talk while we ride...say cute stuff like "I love you" and whatever.

Me: Uh...Okay...

Weirdly enough, the conversation fizzled after that, and I had to go—I had purposefully made it a lunch date so that I'd have an out. Dating tip: Always go Dutch, and always drive yourself on the first date.

Creepy DatesShutterstock

38. Full Of Hot Air

I ran into a guy from high school years after graduation and he invited me to meet up with some of our other friends. Well, when I got to the restaurant, there was nobody else there, just him. Yup. I was ambushed into an unwanted date. To make it worse, he had told the wait staff we were on a date and to take their time. 

TWO HOURS LATER, I was finally able to leave. He walked me to my car, even though I asked him not to. When I went to get in my car, he blocked me and he leaned in for a kiss, which I was not down with at all. It was a dark parking lot and there was nobody around. Super sketchy. I wish I could say that was the worst of it, but it all unraveled from there.

Apparently, something at dinner did not agree with him. I turned my head to the side and went for a friendly hug to dodge his attempted kiss. That's when his bowels UNLOADED. It was the loudest and gnarliest fart I have ever heard. It happened the second the hug commenced and he didn’t let go until it was done. THEN he tried to kiss me again.

I deflected into another awkward hug AND HE DID IT AGAIN. All in all, it went on for at least 30 to 45 seconds. In the end, he made eye contact and said, “let’s do this again.” Hard pass.

Creepy DatesShutterstock

39. Bottoming Out

Oh, I've got a good one. Once, I was on a first date with a guy I met on Tinder. He picked me up for dinner and then we went bar hopping afterward. He grabbed my butt while we were walking down the street. I told him to kindly NOT grab my butt, and he said, "It's my butt now.” I Ubered home so fast and vowed to always take my own car on a first date.

Creepy DatesShutterstock

40. Home Is Where The Creeps Aren’t

He told me, “I know you’re trying to get sober, but I still got you a drink. One more won’t hurt.” Then, when I got up and grabbed my bag, he said, “Why are you leaving? I paid for that, you need to drink it. I’ll walk you home too—I want to know where you live for next time.” Thank God for the security team at the student halls. They stopped him at the gate when I said he was following me.

He knew the halls, but there were 500+ rooms that he would have to get entry to in order to find me. Thankfully, I never saw him again, but he regularly texted me angry messages about not going on another date with him...

Creepy DatesShutterstock

41. Giving “Ghosting” A Whole New Meaning

I went out on a date with a guy whose real name was, I kid you not, the same name as a beloved children's book character. Midway through the evening, he told me he had an ex and she was terrified of his ghost when she slept over. He then told me that eventually, I'd sleep with him, and when I did, he'd sit up in a chair watching me all night so the ghost wouldn't get me.

Creepy DatesShutterstock

42. Did I Get The Gig?

About 10 minutes before we were due to meet, she called and said she had spotted a few friends at the bar. She said she would probably be with them when I got there. That sounded both fine and normal; if a bit intimidating for a first date. But that’s not what happened at all. Instead, it was her and four other strangers crammed into one side of a booth. They all asked me to sit on the other side. 

They proceeded to give me an interview-like panel discussion about dating their friend. I could have maybe gone along with it if my date at least seemed embarrassed, but no, she was fully into it. After a grueling few minutes, I excused myself to get a drink but just went home instead.

Creepy DatesShutterstock

43. No Such Thing As A Free Meal

When I first moved to a new city, I managed to catch a Tinder date. The date itself was just fine and we hit it off. Near the end, though, she made a show about wanting to pay Dutch. Then, when I insisted I was paying, she proceeded to order an extra $40 worth of stuff to go. I immediately told the waiter that the stuff she ordered was going on her tab, and she made a huge stink about me going back on my word.

Creepy DatesShutterstock

44. Baring His Soul

I lost my virginity to a one-night stand when I was 19. We were in my bedroom which faced the apartment next door, so I could see the windows of the people in the opposite apartment. After we had slept together, we were chatting about my view and how I kept my blinds closed most of the time.

Then with a straight face, he said, “At least you can watch people change.” I waited for him to eventually laugh or something to suggest he was joking, but it never happened...

Creepy DatesShutterstock

45. Honesty Is The Best Policy

He told me about all the misdemeanors he committed in his past, about his alcoholism and substance use, and his estrangement from his family. He got everything out for me to hear on the first date, while we sat across from each other sipping coffees. I was actually very impressed with his honesty and openness.

It struck me after being with many different guys who had lied about important things that even though this wasn't the typical kind of guy I would've continued dating, I still really felt he was a good person at heart. He had gotten through a twelve-step rehab program and also made his societal amends while working in a job he liked. 

We went on a second date and it was then that I realized I could really fall for him. Two years after that, we got engaged.

Creepy DatesShutterstock

46. Nice Gams

On our first date, he complimented me in a very intimate setting: “Your legs are so pretty.” I was like “Aww,” and he followed with, “Can I have them?” It turned out, it was just bad humor and an anxious line. He was a complete dork. We dated for a year or so, and he’s a good guy; all things told. Plus, I still have my legs. I call it a win.

Creepy DatesShutterstock

47. Cabin Girl

This girl basically interviewed me while she kept ordering more drinks for me. Then, in the end, she asked if I wanted to be her “winter boyfriend” and spend time with her and her parents at a cabin in Vermont. The catch was that I had to commit to the whole season. "Oh, but we will have our own separate cabin and we will sleep together,” she assured me.

I hadn't even kissed her yet and she still casually dropped that we'd be friends with benefits for a few months. As most red-blooded men would do, though, I took her up on her offer. Her parents were really cool, she was super hot, and I got a free stay in an awesome cabin plus snowboarding for the whole season. She definitely had some form of social disorder, though—she couldn't make any connections with people, and she didn't have a single friend.

Creepy DatesShutterstock

48. Read The Room

He drove me out to the desert for stargazing and a bonfire thing. Yes, I know it was a dangerous first date, but I was stupid and young. Once we found a good spot, he turned the car off and told me, "Now this is where I kill you." He said it with a smile and started laughing. I'm just glad he was just joking but it doesn't make it less creepy.

Creepy DatesShutterstock

49. A Key Moment

He freaking took my keys while I was out of the room and took off into the night. We had an hours-long standoff where he wouldn't answer my calls or texts. I stood by his truck which was parked a few blocks away, just to make sure that he didn't leave with them. Eventually, he dropped them off in my car and I got a ride home from the authorities. Honestly one of the scariest episodes of my life.

Creepy DatesShutterstock

50. To Serve And Defect

He was in the Canadian forces. I asked him if he ever did any volunteer work overseas with his organization and he immediately spat out, "NO! I joined up to kill people, not help people." I chugged my drink and got out of there as fast as I could.

Unreasonable workPikrepo

51. Sowing The Seeds Of Discord

Mid-date, he placed his hand on my stomach and said, "My son will grow here."

Creepy DatesShutterstock

Sources: Reddit,


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