Dating can be extremely difficult. After all, is there any greater task out there than trying to find the right person to spend your entire life with? While the rise of the internet and dating apps have made the search easier in some ways, this has also created a whole slew of new challenges. From adventures with weirdoes to conversations gone seriously wrong, there is truly no limit to how crazy things can get when one meets up with a stranger from the internet. Here are 50 stories about some of the worst online dating experiences that people have ever had.
1. A Change of Plans
I was really hitting it off with this guy I had met on Tinder. Or at least I thought I had been until a few dates later when he broke down crying in the middle of a heated makeout session telling me that he felt nothing and thought he might be gay…
2. Drinking and Diving
I once met up with a girl I had spoken to online. We went to a bar in Philadelphia on a Friday night at around 6 PM. It was fun and we drank a lot, but I noticed that she was pacing her drinks much faster than me. I had around four beers in the time it took her to drink seven martinis. The martinis were costing me $15 a glass.
We are getting along well and then she says that she needs to use the restroom. For some reason, she took her jacket and purse to the restroom with her. I didn’t think much of it at the time. But after an hour of sitting at the bar alone and waiting, I realized that she wasn’t coming back and that I had just gotten used for a heavy pregame.
The bartender kinda realized what had happened. When I asked him for the tab, he shrugged and was like, “Stuff happens, mate. I took two drinks off your tab.”
3. You Need a Better Opener, Buddy…
Oh man, the first time I ever contacted someone on a dating site, I made a huge fool of myself. It was via The Onion personals, which were really a thing back in 2005! Thinking I was being flirty, I just made fun of a band she said that she liked. I wrote something to her like, “My only problem with you is that you are into that band!” She replied, as she should have, “My only problem with you is that the only thing you offer is a criticism.”
I still cringe every time I remember this.
4. A Picture Is Worth a Thousand Words
One time, I was talking to a girl online who had mentioned that she was into photography. Naturally, I asked her to send me some pics. She thought I was asking her for naked photos, so she immediately deleted and blocked me. I quickly realized that I had worded the question poorly, and I wanted to try and explain myself, but she had already blocked me before I had the chance.
5. Duck and Cover
I have a pet duck, which I think is pretty cool and impressive. So, naturally, I wanted to have my online dating bio say “I have a duck.” Seems simple enough. Unfortunately, though, I accidentally put an “i” instead of a “u” in the word “duck.” I’m also a girl. Let’s just say I did not get too many matches…
6. There’s No Place Like Home
After a few OkCupid attempts, I finally ended up dating this one guy a few times. Eventually, he asked me if I’d like to come to see his apartment and I said yes. When we got there, he had loads of swords and machetes all over the walls. He also decided to hold one up to my throat to show me how incredibly strong it was. So yeah, there was that…
7. Bot or Not?
I once matched with a girl online who looked really cool. I complimented her hair. She responded with something along the lines of: “I’m so glad you messaged me! Most of the guys on here just match and never message.” I’ve seen almost the exact same line before from bots, so I assumed she was a bot and said something very snarky about it. She replied, upset, and then unmatched me. How could I have known?!
8. She’s Not Getting the Message…
I once tried using Plenty Of Fish, the free dating site. It was like the discount supermarket of dating sites. I chatted briefly with one woman before telling her that I was going out to grab a few drinks. The next day, I checked my messages and saw that she had sent a few while I was out. Let’s just say they changed my opinion of her pretty drastically…
They started out with “You’re getting drinks? Why don’t you come around to my place and get drunk with me!” From there, they progressed to “Why are you ignoring me?” Then to “I think you’re gorgeous, and we would be really good together!” Then, finally to “Don’t you ignore me, you little jerk!” I sent her a message bright and early the next day asking her to never contact me again.
9. Not a Good Time for Memory Loss
I once met up with this very attractive woman who I had found on the upper-middle-class version of Tinder. You probably know it as Bumble. She was way hotter than me and I kind of wondered in the back of my head what it was that she had seen in me. I decided to put the question out of my head though and just tried to enjoy the date.
At some point during the evening, she suddenly leans forward on her barstool, narrows her eyes, stares at me intensely for a few seconds, and then goes, “Now I know there was some reason that I swiped right on you, but I just can’t quite remember what it was!” Well gee, that was exactly what I needed to hear!
10. Not Exactly Child’s Play…
I once went on a date with a girl from Tinder who told me pretty bluntly that she found children very attractive. After hearing that comment, I stopped mentioning that I had a child on my profile. I also took down the pic of me and my daughter. From then on, I only brought this fact up with the girls that I felt were likely to stick around after meeting me in person.
11. This Is How She Rolls
I messaged a cute blonde girl on a dating app one day. I got a response from her and, after a while of back and forth making each other laugh and getting along, I mention that I’m in a wheelchair. As soon as I said that, she suddenly lost her entire mind. I have literally never seen anything as petty and offensive as what she said next.
She started ranting at me and whining about how my disability would ruin our future. She complained about how she wanted to explore places like Australia, and that I wouldn’t be able to do that with her because of my wheelchair. I let her go on for a while to see if she’d ever bring it back around to a normal person’s thought process. But that never happened. She totally lost her mind.
12. A Tall Tale
I matched with a girl on a dating site one time. She had a very pretty face. All of her pictures were mostly only showing her face and upper body, but I didn’t really notice. She initiated the conversation and wanted to come over, so of course, I said sure. She arrives and I answer the door. I was not expecting to see what I saw next.
It turned out that she was about 6’5″ tall. I am 5’8″ tall at best, on a good day. I let out an audible “Holy cow!” when I noticed the difference in our sizes. That was when I realized why she had hidden her body in all of the pictures on her profile. Nevertheless, she walked through the door, picked me up, and carried me up to the bedroom like a baby. No regrets.
13. It’s All in the Game
I tried Tinder for a while. After a month or so, I contacted and was talking with this girl and things seemed to be going well. We had similar interests in music and movies, similar senses of humor, etc. Eventually, we were talking about hobbies and I casually mentioned that I played this one video game. She immediately unmatched me. Like, she took the time to receive the message, think about it, choose not to respond, click the menu, and hit unlike. Just because of my video game preference.
14. A One-Track Mind
This cute girl on Tinder sent me a one-word message: “Hi.” Okay, it’s not easy starting a conversation, so no problem. I replied with a medium-length message. I commented on some interesting hobbies that she mentioned in her profile and asked for more details. I also told her about my day, and some other random stuff.
Overall, it felt like a good effort. Yet I got no response. I was pretty disappointed. Then, out of nowhere, I received a new message from her the next day. It said: “Hi, how are you?” I literally didn’t know how to react. I didn’t reply and I’m assuming she’s either a bot, someone with zero social skills, or someone who just isn’t serious about dating.
She was pretty, though.
15. One Thing Led to Another
On a dating app, I once talked to a girl who lived in a town 25 km away. She was nice and pretty so I asked her if she wanted to meet up. She said yes, so we met up at her farm. I soon discovered that she was a terrible conversationalist. I couldn’t get her to talk about anything and, when I talked about myself, she seemed really bored.
I was halfway through a sentence before she interrupted me to suggest going to the town’s local takeaway shop for some food. We went there and were still having a terrible conversation, so I decided to talk about my trip to London. Somehow, that actually got her going. She talked for five minutes straight at that point.
She told me all about how she had always wanted to go to Canada as a little kid, and that the next year she was finally going…to get married!! Honestly, I thought she was joking at first, but I later realized that she was completely serious about it. As you might have guessed, the rest of the date went pretty lousy from that point on.
We also didn’t watch a movie like we had planned to. Instead, we watched the end of a movie that she had started watching the night before. Also, when we were at the takeaway shop, she took one bite of her hamburger and threw up in the toilet for ten minutes because apparently it was too greasy or something.
She then suddenly remembered that she had to go pick something up from a mate’s place, 70 km away. She told me that I needed to leave immediately, so I did. I obviously had no interest in dating her after that, but the next day I still decided to text her and ask how she was. She had mentioned going through depression recently, and I didn’t feel right just ignoring her after that. It’s been almost two years since that date and I’m still waiting on the reply…
16. Two Birds with One Stone
One time, I chatted with a guy who said he worked as an actuary. For those who don’t know, an actuary is essentially a company’s risk manager. Being the idiot that I am, I thought he said an aviary. An aviary is a giant birdcage. I assumed he worked with birds and kept repeatedly asking him bird-related questions. After a while, he blocked me. He must have thought I was insane.
17. Here Today, Gone Tomorrow
I once went on a date with a girl I had met online and thought things had gone pretty well. Then, just two weeks later, I got some shocking news. I was told that she had passed due to the sudden development of an extremely rare disease. I was suspicious that the story might just be an extreme excuse to keep me away, but to my surprise, it turned out to be true.
To this day, I’m convinced her passing was because she went on a date with me.
18. All Taco, No Action
One time, a girl on a dating app posted “Buy me Taco Bell” in her About Me section. Being the ridiculous person that I am, I jokingly messaged her and said that I’d take a taco and slap it across her behind. I knew that this was a silly and ridiculous thing to say, but I thought it was funny and did it for my own intrinsic kicks and giggles. A few weeks later, I deleted my profile.
Then, many years later at some art show, there’s a girl who’s sharing a book she’s published about the disgusting things men have said to her via online dating. I open the book and immediately spot the words “I’d take a taco and slap it across your behind.” I look the author in the eyes and tell her that men are disgusting and that whoever said that is a piece of trash.
19. Alright Then…
I once chatted with a guy online for a few weeks. He seemed normal and nice and we had a lot in common. We flirted quite a bit and then eventually met up. This is when he tells me he’s married. He also informs me that he used to be a teacher and wants to humiliate me by making me spell words while he spanks me. I just…
20. Horrible First Impression
I met this girl online. We hit it off and agreed to go out. I picked her up and immediately got mauled by her dog while she and her roommate just watched. Then, on the way to dinner in my car, she revealed that she had very strong feelings against vaccinations. I should have just stopped right there and said this wasn’t going to work out. I could have saved myself the cost of dinner.
21. Don’t Drink and Text
I once spent an entire evening chatting up an attractive young blonde on a dating app, while drinking copious amounts of whiskey. I eventually got some courage up and invited her to go for a walk with me sometime. That was the last thing that I remembered. I woke up in the morning assuming that I had a date with her that evening.
Nope. I looked at my phone and read through the previous night’s messages to see what had gone wrong. I must have gotten a little annoyed when she declined my offer for a walk because I apparently badgered her about it for a while. Well, that’s when I realized my biggest mistake. It turned out she was in a wheelchair. And somehow I didn’t notice that in the pictures.
22. Losing to the Competition
My fourth date on a dating site went horribly, much like most of my others did. I thought this girl was perfect and we actually spent the whole day together. When I got home, we still kept talking and I thought this was a sure thing. Two days later, she stopped messaging me altogether and then told me a few days later that we needed to break things off because she had recently started seeing someone else and felt bad just abandoning him like that. It broke my heart.
23. Guess Who’s Coming to Dinner
I’m currently serving overseas in the Navy and I got very bored one day. So, I thought what the heck and decided to give online dating a shot. So, I’m on the site just messaging a few random girls and I start talking to this one girl who seems pretty nice. We realize that we have a lot in common and agree to grab dinner one day.
When the big day comes, we finally meet up and grab dinner. Over the course of the meal, I not only found out that she lied about her age, but also that she was the daughter of one of the chiefs on my ship. Yea, that was a pretty important detail for me to know about. There was not a chance I was gonna be down for that.
24. Maybe Second Time’s the Charm?
I recently gave in and signed up for my first-ever online dating profile after years of avoiding it. My first message came from a man who was quite a bit older than me. It read: “Hey there. Do you wanna come over and use the toilet while I tweak your nipples?” Umm, no thank you. I promptly deleted my account and never looked back.
25. Oh, There’s Just One Little Thing…
Me and this guy met each other online. He seemed cool and funny at first, and we went out a few times. I was enjoying myself. But then, a few weeks in, he told me that I was almost perfect, except for the fact that my upper arms were fat. I think he meant it as a compliment, but the second part was all I could think about. It was the specificity of his complaint that made it seem exceptionally cruel.
26. A Case of Mistaken Identity
I once tried online dating and agreed to meet up with a girl who had described herself as a 24-year-old student with long, blonde hair. I arrived on the date all happy, but then realized that the woman who was joining me was actually a 40-year-old lady with two children who was just trying to find an excuse to leave her house.
27. More Proof That People Suck
This girl I knew had an online dating profile but was a bit overweight. She had something like only two responses in more than two months on the site. As an experiment, she made another profile and used word for word the same exact description of herself, but with no photograph. This time, she got over 50 responses in the first week. That fact made me very sad. I can only imagine how it made her feel.
28. Stuck in the Past…and the Future
I once met up with a girl from a dating app over coffee. She was a couple of years older than me but she seemed sane and normal. She was also very attractive. Two minutes into our casual warmup conversation, she starts talking about her multiple exes and how she would stalk them at random times at their places of work.
By the time I managed to get her off of this topic, she had moved on to talking about me. Specifically, she was talking about what our perfect life together would be like and how she’d secure our love. Then, she started demanding the passwords to my Facebook and email accounts. I walked out shortly into this, and she made a grab for my car keys.
29. Mixed Messages Is an Understatement…
I was messaged one time by a girl on Plenty of Fish. Let’s call her “Ashley.” One of those conversations we had immediately took off and we were talking for at least four hours straight. We decided to go out and get dinner. She was even better in person. Beautiful, witty, laughed at my stupid jokes, and the whole bit.
At the end of the date, we exchanged goodbyes and that was the conclusion of our evening. We continued texting until about midnight, at which point she abruptly said: “You’re going to hate me, but I think we should just be friends.” So I’m like okay, whatever. Disappointing, but there was not much I could do about it.
But it got weirder. The next day, she calls me and apologizes, saying that she changed her mind. So, I give her a second chance. At the end of our second date, we start making out like we’re in middle school. A few minutes into this, she stops us before we get too far and says she’s not ready for anything like that yet.
Okay, cool. I can respect that. Then, I get home and she texts me, saying that I was just going to use her for her body and calling me a pig. Um, okay? I let it slide and just put the whole thing out of my mind. Then, the next day, I get a text from Ashley’s phone asking if I know where she is, as I was the last person who had talked to her before she “disappeared.”
Apparently, her “friend” had shown up at her house, where Ashley had apparently left her phone and her car and the front door was wide open. So, I told this mystery person to call the authorities. When she refused, I said that I would. Right then, lo and behold, Ashley showed up. “I had just gone for a walk. Didn’t know you cared about me so much!”
Yeah okay, at this point I’m totally done with this situation. The next day, I go to work. I usually leave my phone in my truck until lunch. When I went out for lunch at noon, I had 115 new texts and 48 missed calls. All from her. Yup that’s it. I’m officially done. So I block her number and assume that I can finally move on with my life.
Wrong again. She knew where I worked and roughly what time I got off at. She showed up outside my work the next day as I was leaving. My workplace is almost an hour and a half away from where she lived. She tried following me home. I took a roundabout way of getting home and even ran a few red lights until I eventually managed to lose her. It’s been almost a year now, and I haven’t heard from her again since.
30. On Their Ninth Life
I thought I was getting lonely, so I signed up for Plenty of Fish. This is what I got: a man with kids, even though I specified “no kids;” a man about 25 years older than me who wanted “no strings attached;” several illiterate rednecks; and a guy who was more into Star Wars then Star Trek, even though I specified Star Trek!
Oh, and how can I forget the guy who boldly stated that he wanted his woman “barefoot, pregnant, and in the kitchen.” After that last one, I said screw it, and I have never gone back to the site since. Not even one single time. If I ever get lonely, my cat will cuddle with me. I would rather have that than have to deal with any of these crazy people…
31. In Close Proximity
I don’t use dating apps. However, my roommate loves them, and she’s brought back numerous visitors as a result. Which is fine, except for the fact that our apartment is tiny and we share a room. And also the fact that my roommate doesn’t really care what I end up seeing. And, believe me, I end up seeing a lot…
On top of that, as it turns out, most guys on these apps don’t seem to care about having another girl in the room while they’re over! Some even take it as a potential opportunity for a threesome. If they knew me at all, they would know that I am not even remotely interested in that, but they can still dream. I guess what I’m saying is that my dating app horror story is knowing my roommate!
32. Parental Guidance
I once went on a date with a girl that I had met on Tinder. When I arrived to pick her up, I learned that she had already told her whole family about me. Again, this was before we had even met. Then she told me that she wanted me to come inside and meet them in person. This was the first date. Am I missing something? No thanks.
33. Does the End Justify the Means?
This was back when Tinder first came out and wasn’t quite as sketchy as it is today. Me and this girl met up and had a great first date. The second date was even better. Things kept going well for about two months, when she told me that our whole relationship was just a social experiment gone wrong. I had no idea what she meant.
Apparently, she had created an account on Tinder just to see who she would meet and to show her friends that she could get any guy she wanted to buy her dinner. She also was competing with them to see who could come back with the craziest story about their worst Tinder date. In the end, we both really liked each other, but I was shocked to learn the truth about how we started.
34. Car Trouble
My buddy isn’t the smartest man around. He once met a girl on a dating app, picked her up, and drove with her to a motel. They were walking into the room when she suddenly said, “Oh wait, I forgot my purse in the car! Do you mind if I go grab it?” He says, “Yeah, that’s fine,” and tosses her the keys. Five minutes later, he walks outside wondering where she is. His car is gone.
35. Appearance Versus Reality
This woman I had met online seemed really cool. We were both 25 years old. She had just finished her Masters and was job hunting. She was fit, witty, and had piercings. I was a fan. After some time talking online, we finally met up. Well, the photos in which she was fit were apparently from five years prior, and she looked very different in person.
She insisted that those photos were on there because she was “trying to get back to her normal weight,” and so she thought it was totally appropriate to use photos showing how she will look in the near future. I’m talking about a 70 to 85-pound difference between photo and reality. At the same time, I figured we could still be friends. She had always been very witty in our online conversations, which I liked.
So, I strike up a lighthearted conversation. But where’s all the wit? I toss her a couple of verbal jousts to try and get a funny reaction out of her. Nothing. Turns out her roommate had been helping her reply to my messages. That’s cool, I can still be friends with nice people that aren’t witty, right? Okay, well then it turned out that her nose ring was actually just a weirdly shiny wart that she intentionally tries to pass off as a nose ring because she’s embarrassed by it. Kind of off-putting, but I probably shouldn’t judge someone by something they can’t control, right?
All of this I could live with. But it still wasn’t the worst part. We were out for dinner and went to a decent gourmet pizza joint. Low lights, thin crusts, and fancy drinks. Then, out of nowhere, without asking me, she reaches over and starts picking toppings off of my pizza. Pardon me, missy, but keep your darn hands off my prosciutto! It was unforgivable.
36. Raising Some Red Flags
I went on a date with a guy and, the entire time, he was talking about how men are superior and how there have been scientific studies to show that “women have an emotional reaction to the color red whenever they see it.” I wonder why he was still single…
37. A Story with Substance
At one point in my life, I dated someone I had met on Tinder for an entire month. She seemed totally perfect on paper. She was a Master’s student, a yoga teacher, highly cultured, etc. Then I found out that she had been using illicit substances on a daily basis and didn’t even consider it to be a big problem.
I actually had to sit her down one day and explain the definition of a high-functioning addict to her. She had never heard of this concept before and essentially felt that having a job and going to school meant that her substance use was not a problem. We broke up soon after that and she immediately went back to her sketchy ex-boyfriend. Bullet dodged!
38. Carrying a Heavy Burden
I’m a chick of the heavier variety, and I always post a current body shot because I don’t like people wasting my time if they’re not going to actually be interested in me. I honestly never understood why people post misleading photos. Like you don’t think that people are going to notice the difference when you meet up?
Anyway, I was talking to this guy online one time. He seemed nice enough and he eventually asked to buy me dinner. I said sure. He had only posted a face shot on his profile. When we met up, he was easily clearing over 450 pounds. I was not really into that, but I stuck it out anyway because he seemed like a nice person.
We grabbed some coffee first, and then we walked over to a nearby restaurant. Now, I’m no athlete, but I do like to hike and do other outdoor activities. I may not be winning any marathons any time soon, but I can walk for miles. This poor dude was wheezing within 20 feet of walking. Clearly it was a major effort for him.
I felt bad for the guy. Even though I try to be open-minded, I just can’t date someone who is that unhealthy. We get to the restaurant, which was really good, and he tells me about himself and his life. He told me all about his roommate who was dating a heavy substance user. Apparently the couple was not very pleasant to be around.
They would sleep together all over the place, even with the doors open, and would do all kinds of inappropriate substances. According to his account, they were just jerks in every way you can imagine. He also told me he was into some weird and pretty extreme stuff in the bedroom and implied that he wanted to try some of it with me after dinner.
I said I had to leave right after dinner and scooted away from there as soon as it was polite to do so. Then, six or seven months later, I decided to try my luck on the app again. This time, I was going out with a guy who said he was a photographer. We got along alright and he seemed pretty cool. I had nothing to complain about at first.
The conversation went well and, over the course of the date, he asked me about bad dates I had been on in the past. I brought up the larger guy from before and mentioned the wheezing and his weird requests. My new date asked if the guy was named so and so. My jaw dropped. Turns out I was currently on a date with the first guy’s roommate.
Let’s just say I don’t use dating sites anymore…
39. Your Number One Fan!
I once showed up at a restaurant to meet a guy I had been speaking to online. I waited about 30 minutes for him but he never showed up. Finally, I ordered myself some food and was about to leave when he texted me, saying: “Sorry I didn’t make it. Also, there’s a liquor store across the street from the restaurant. Can you pick me up two six-packs?”
I told him I wouldn’t. He explained that he had decided to play frisbee with his dog instead of keeping our plans. I immediately deleted the app, went to said liquor store for myself, picked up some drinks, and went home. Believe it or not, the guy still continued to text me for a month or so after this! And it got so much creepier…
On one occasion, he texted me to let me know that he had just bought tickets to see me dance. I’m a retired ballerina and haven’t been in anything for a few years. I have no idea how he found out that I was going to be doing a show. Then, he texts me an hour after my performance and tells me how great I was on stage. I never responded.
Dating is too confusing. I’m all done.
40. You Don’t Belong Here!
My online dating nightmare was when my friend spotted my then-girlfriend, now ex, on Tinder with an active profile. He was a bro and immediately told me about it. I couldn’t believe what I was hearing, but he had the evidence to prove it. I broke up with her the next day. This felt like a nightmare at the time, but I’m glad I found out.
41. Paper Trail
I started talking to this really sweet guy online for about two weeks and things were going well. Then, I started getting calls from this girl who he claimed was his crazy roommate that was in love with him. Apparently, she was constantly trying to get him fired from jobs. Turned out she was actually his live-in girlfriend. Apparently, he wasn’t a citizen and was hoping to secretly obtain papers through courting and marrying me.
42. Sounds Like the Whole Enchilada
En route to the date, this guy I had met online texted me from the burrito place we were meeting at to tell me that he had already ordered me the salad. I repeat: the salad. At a burrito place. Also, was I a little child or something? Was I now incapable of placing my own food order or deciding what I wanted on my own?
Anyway, after arriving, with my salad ready beside his delicious-looking plate of tacos, he spent the next half an hour telling me all about his model ex-girlfriend and how passionate their habits in the bedroom had been. Apparently, they had just broken up the previous weekend and it seemed to still be on his mind. Awkward…
43. Looks Can Be Deceiving
I met my Tinder girl at the train station. She wasn’t the most talkative of sorts, but I maintained conversation all the way up to the bar that we’d agreed on earlier. Only when we got there, she refused to go in, saying she didn’t like “the look of it.” We carried on down the road with me maintaining most of the conversation.
We passed nine more bars that she also didn’t like the looks of. By now, we were walking in near silence. So, I steered our walk back towards the train station, ready to call it a day and head home. But suddenly, my Tinder lady stopped me and pointed at something, saying “That’s what I want! I want to go there!” It was a van selling frozen yogurt.
44. Strangers on a Train
My first and only ever Tinder date lasted a total of about 30 seconds. I met the girl at a nearby subway station. She walked out of the station, looked at me, said “Sorry, I don’t like you,” and left. I was in utter shock. I couldn’t believe that someone would do something that outrageous. It was literally a real-life swipe left!
45. Maybe She’s Just a Workaholic?
I once met a girl from a dating site at her workplace on a moment’s notice. She was a waitress and there was literally nobody else in the entire place, so she asked me to stop by and hang out with her for a bit. We talked for a few hours, and I thought we were really hitting it off. Then, things took a very weird turn.
As we’re sitting there and talking, another dude suddenly shows up to meet her. He says he’s from Tinder. Yes, she accidentally double booked herself with two guys to keep her entertained at work. As if that wasn’t bad enough, she later blogged about the experience and described me as “dull and unattractive.”
46. The Mad Hatter
My first ever online date showed up in a white suit and a white fedora. He later asked me if my menstrual cycle lined up with the cycles of the moon. He ended up talking for the entire date and I, being too polite to do anything about it, let this go on for several hours. He told me at the end of the date that he had never felt such a strong connection with anyone before.
47. A Nasty Hobby
I am a girl who likes to date other girls. Most girls who like to date other girls are fairly liberal since most conservatives aren’t so into ladies loving ladies unless they get to watch. Anyway, I’m meeting this one girl from a dating app for coffee in DC. She seems cute and sweet and funny. She told me that she works for a think tank in Dupont, which is true of like 70% of the non-hetero girls that I know.
We are having a great conversation about weird stuff that our families do, and I mention that my mom is trying to learn how to use Twitter. She then mentions that she, in her spare time, runs a Twitter account where she sends hate tweets and angry memes to Democratic politicians and their supporters. Ya know, just for fun! She couldn’t understand why I didn’t think this was funny.
There was no second date.
48. In Real Life
There was this one person I matched with on a dating app and really thought I had hit it off with. The two of us chatted regularly for about a year, even by phone. Then we finally met up in person when we found an opportunity. Once we actually met, we had nothing to talk about and it was the most awkward encounter of my life.
49. Too Much, Too Soon
I once matched with someone on a dating website back in the days before Tinder. We got to talking and he seemed like a chill dude, even though there were a few red flags. For example, he insisted that we were a couple before we had even met and that I wasn’t allowed to talk to anyone else. In spite of this, I agreed to meet up with him at a cafe by my work.
I organized with my receptionist that she would call me at a certain allotted time and tell me that I had to come back to work. That way, I had an out. I met with the guy for coffee. It seemed well enough. Then, my girl rang me, so I told him I had to get back. His response was: “I’ve got my work van here, do you want to jump in the back and have a quickie?”
I got the heck out of there and went back to work—but the story didn’t end there. A couple of months later, he ended up coming into my office to see my boss. I made polite small talk with him. Then when he left, my boss called me into her office to ask how I knew him. Turned out he was married to my boss’ niece and I had dodged a huge freaking bullet!
Thankfully, my boss believed me when I told her what had happened and we never spoke of the matter again. I was too embarrassed to ever raise the subject again, anyway, because I generally prefer to keep my private life private. I assume she never raised it again because she probably wanted to keep it between her and her niece.
My boss was also a black belt in jujitsu, so not exactly a person I was looking to get into drama with. Yes, I should have known better and ended things when the guy got possessive straight out the gate, but I was young, insecure, and lonely. It’s not a crime to want to be wanted, even though I was definitely a naive fool.
50. A Lot of Reverse Psychology Here
Someone, without a profile pic, messaged me out of nowhere saying that she didn’t like typing on her phone but wanted to meet up with me for a breakfast date someday. I generally only go out with people that I’ve talked to for a bit beforehand, but her profile said she worked in psychology and I’ve usually gotten along well with psychologists on previous dates.
So, I just decided what the heck and went for it. What did I have to lose, right? We scheduled a time to meet up at a nearby restaurant and, of course, she just didn’t show up. Fortunately, I just gave up after 20 minutes. She apologized later in the day, mentioned that she had accidentally overslept her alarm, and offered to make it up to me by going out for coffee that same evening.
For whatever reason, I agreed. I get to the cafe and, sure enough, I’m waiting for yet another 20 minutes past the time we were supposed to have been there. Thankfully, though, this time she had texted me to let me know that she was on her way just as I was leaving. So, after the 20-minute delay, she finally showed up.
Surprisingly, she was pretty physically attractive. But that’s kind of where the attraction ended. Over the course of the date, she did just about everything wrong that you can possibly imagine. She continuously gave me negative feedback about everything that I was saying. She said that she didn’t believe in the opioid epidemic and that I was an idiot for thinking it was real.
She said she didn’t believe that mental illnesses were real and that you could just get over them if you tried hard enough. After some questioning, she eventually revealed that she wasn’t actually a practicing psychologist. She just had an undergraduate psychology degree and was currently working as an Uber driver and a grocery store cashier.
She later revealed that she had two kids, but said I didn’t need to worry about them. The reason I didn’t need to worry about the kids was that the courts took away her custody of them and gave them to her parents. I also apparently didn’t need to worry about the fact that she was still married, because her husband was incarcerated.
She also assured me that they were in the process of divorce. Then, as if I hadn’t heard enough already, she spent a significant amount of time complaining about how messed up the court system is for thinking that she’s unfit to be a mother. Now, as bad as this all sounds, none of it was the worst part. That came at the end.
My actual mistake came when she mentioned that she would really love to meet my dog and play with him. I’m a bit naive sometimes in dating situations. So, I thought that, since my dog loves people, it would be a nice opportunity for him to get to play with someone new. I figured at least something good might come out of this trainwreck of a night.
Needless to say, she was not actually interested in playing with my dog. When we got back to my place, she pretty much completely ignored my dog and instead kept trying to pull me onto the bed. I use a giant beanbag for a bed and it’s in the living room, so this wasn’t hard for her to do. I’m weird, I know. But that’s beside the point.
I was not interested in sleeping with her. I’ve been in relationships with unstable people before, and it’s just not worth it. But she wouldn’t stop. She kept undressing more and more was getting frustrated at me for just standing near the door and not getting into it. I kept politely mentioning that I was tired and needed to work in the morning so it was probably best if she left.
But she refused. She kept saying that she was too tired to drive back home and that she needed to take a nap here. Given that she seemed unstable and that I was now realizing the gravity of my mistake, I said that this was fine and I set an alarm for her. Though, of course, when the alarm went off, she still refused to leave.
So, I ended up with a clothingless, mentally unstable woman passed out on my beanbag while I sat in a chair hunched over my laptop working all night so that she couldn’t try anything. Fortunately, when the morning came, she did finally leave. The whole experience was really unpleasant and I was happy to be done with it.
Then, a few days later, I got a really angry text from her because my dating profile was still up on the dating site. Apparently, she had thought we were in love now. I told her that I didn’t feel the same way. Fortunately, she didn’t remember what apartment I was in. A few weeks later, the building’s security guard mentioned to me that someone fitting her description had asked which apartment I lived in. Luckily, he didn’t give an answer.