Dating isn’t easy. We all want to find true love, but people we have high hopes for often turn out to be very different than the way we envision them. But not all bad dates are created equal. Sometimes, two personalities just happen not to click. Other times, one of the people turns out to be legitimately crazy. Those crazy people might not make for good relationships, but they definitely make for good stories! Here are 50 unbelievable tales about some of the worst dates ever.
1. Double Whammy
I once took a girl out for sushi as a first date. About ten minutes into it, I got a call from my boss. Ordinarily, I wouldn't have taken the call, but this is not the kind of guy that you can ignore without some major consequences. I went outside to take the call where the guy berated me throughout the entire conversation. Great—but it gets worse.
He ended it by saying he's sorry he interrupted my dinner but he's not sure I understood what it takes to be his assistant. I walk back in, my confidence utterly destroyed, and proceed to be completely in my own head for the rest of the date. As I dropped her off outside her house, she says, "You might be the most awkward person ever".
The next day, I was fired.
2. The More You Know!
I met this girl and hit it off pretty well with her. I hang out at her place one night, get home, and decide to look her up and add her on Facebook. As soon as I look her up, I discover that she has an eight-month-old kid and a husband in Iraq. Both details she decided to leave out. When I confronted her about it, her response was unbelievable. She just said, "Well, I didn't think that would bother you".
3. Law and Order
I once went on a date with a law enforcement officer. My mom set it up but it seemed like he was an alright guy, so I agreed. We went out to lunch. He proceeded to tell me about his kids and talk about his hobbies. Afterward, he offered to show me around the town since I had just moved here. Turns out he was actually driving over to his ex-wife's house to introduce me to his kids.
They seemed to not be home, so he went to the windows and peered inside to make sure. At this point, I just wanted to be out of there. When he got back in the car, I politely asked him to take me home. He did, and I told him I'd call him sometime that week. I never called him, and for about a month I was completely paranoid that I'd get pulled over by one of his buddies.
4. Pick a Partner
My prom date was pretty bad. It was a double date with some girl I'd never met. Turned out we had both just been dumped. I tried to make conversation about random topics, but she just wanted to talk about how annoying her ex was. We get to prom and it turns out that her ex, who I'd also never met, was there—but that’s not the worst part.
He was there as my ex's date. My date then spent the rest of the evening trying to get her ex to come back to her.
5. Memory Loss
This is not the worst thing that ever happened, but it’s still kind of funny. I once took this girl out for a first date. We went to a play and then out for drinks at a bar afterward. While we were enjoying our drinks, she suddenly stopped me in the middle of our conversation and said: "You don't remember, do you?" Turns out we had slept together like five years earlier…
6. Dinner and a Show
I would have to say that the worst date I ever went on was the one with the girl who came to my house to "make me dinner". She showed up with a bottle, popcorn, and a movie. We consumed it, and she decided it would be fun to run around our neighborhood, screaming and doing cartwheels in the streets. I said sure. Out we went.
She climbed a tree. I climbed the tree after her. We slept together in the tree. What was so bad about this date, you ask? One of my annoying, silly sperms decided to go and fertilize one of her eggs. She had a miscarriage when she was about three months along. I was not looking forward to having a child with this crazy girl...
7. Viewer Discretion Advised
About a month ago, I took this girl out to dinner and, on the way back to her house, she said, "So what now?" I was like "Hmmm, I don’t know". Then she said, "How about a movie?" So then I responded, "Sure. Do you want to go see one or just watch one on (insert accidental reference to an adult site here)?" She looked at me in shock, at which point I realized my mistake and became super embarrassed.
8. Constructive Criticism
My worst date ever was with the girl who, for no apparent reason, picked a fight with a construction worker on our train ride home and then pushed me into the guy to defend herself. Yea, being used as a human shield is not exactly my idea of a good time.
9. Food, Glorious Food
I once went out on a date with this guy who ordered a ton of food to our table and then refused to eat any of it because he was apparently on a diet. That probably would have been a good thing to mention earlier on. He just sat there and watched me eating on my own the whole night as he told me a whole slew of extremely detailed stories about his gambling problem.
10. Pop Goes the Weasel
I once went out on an eHarmony date to a high-end bar with a huge beer selection. The girl shows up and she doesn’t look anything like her photos. She proceeded to drink seven Miller Lights, then proceeded to tell me some very weird things. For example, she told me that the reason she didn't want to be single anymore was that she missed having someone to pop the zits on her back.
At the end of the date, she asked if I wanted some gum. I politely declined. She went in for a kiss and I turned it into a hug instead. Needless to say, this was the first and last date that we had together. No zit-popping for me.
11. Waiting for a Friend
I once had a date show up late the first time that we ever met up. Apparently, she had decided that she wanted to go out for a few drinks with her friends after work. So, I was the lucky guy who got to sit around waiting like an idiot while she was doing that. I then had the pleasure of waiting outside of a locked door for about 20 minutes when we stopped at her place for her to get something on the way to dinner.
12. Thems’ Marryin’ Words
I picked up my girlfriend one evening, planning on proposing to her. I took her to one of our favorite parks and surprised her with a picnic, which we both enjoyed. When we were done, I sat on the ground next to her, looked into her beautiful green eyes, and said "I love you so much. Will you marry me?" She replied with a shocked look and said something like, "Oh sure, whatever".
My proposal had caught her off guard and went completely over her head. So now, in my mind, I am thinking, "Oh, you idiot. You screwed this up bad". And then, out of my mouth, came the stupid words: "No you idiot, I'm proposing to you!" Chalk that up to an extreme case of nerves. On the bright side, despite her confused expression, she said yes and we've been married for 11 years now. Our first child is due in a few days.
13. A Shot in the Dark
A guy I was dating turned out to be a seller of illicit substances. While we were out for one of our first dates, he stopped in the middle of a bad neighborhood and left me in an abandoned parking lot alone for a good half hour so he could, "get something". He came back with a jar full of every illicit substance you can possibly imagine.
During our kiss goodnight, let's just say my hands "wandered". What I thought was his belt buckle turned out to be a weapon. Naturally, my instinct was to say, "Hey, so why are you armed right now?" To this, he replied, "I just want you to know that when you’re with me, you're safe. Hey, wanna go into the woods and shoot stuff?"
As soon as he said that, I lost all interest in hanging out with him. I began to worry that by "shoot stuff" he might have meant shoot me. So I politely turned down his offer to go and shoot stuff. However, I still agreed to see him again and I, unfortunately, continued to date him until he wound up behind bars. Not the best decision I’ve ever made.
14. Baby It’s Cold Inside
I once met up with this young woman for dinner. She was never married and had no kids. She got super weird and ended up saying a lot of crazy stuff. I could write an entire story about the evening, but here's the kicker. At one point, I saw her eyes light up as she apparently remembered that she hadn't told me something important".
OMG, I haven't shown you my daughter!" she shouts out. "Hmmm, what's this all about?" I wonder. I thought she said she didn't have any kids. The woman then reaches into her purse, pulls out an old Polaroid photograph, and hands it across the table for me to have a look at. I was not at all expecting to see what I saw next.
It was a picture of her sitting in a hospital room chair with some guy’s arm over her shoulder, both smiling at the camera. They were holding a stillborn baby! At this point, I had no reaction. It had been three hours into the night and an ever-increasing string of surreal events had broken my level of interest. I just handed the photo back and said, "I've got nothing to say about that".
15. The More the Merrier
Here are some of the highlights of the night that I went on my worst date ever. First of all, the guy showed up two hours late. Normally, I would have just left, but we were meeting at a festival in a big city. I took the train for an hour. As I was getting off my train, he called to tell me that he missed his and had to wait another hour for the next one. We missed the festival as a result.
He had also lost his phone that day. So, not only was he calling me from a friend's phone, but he also brought three friends with him. He and his friends brought a case of drinks and consumed all of them as we wandered the city and its parks. He made fun of me when I didn't want to use some illicit substances with them on the same street my school was on.
Since I was starving, we went to a place that I ate at all the time in college. After ordering three drinks and dinner, he realized he forgot to mention that he didn't have any money on him. At the end of the night, he shoved his tongue down my throat and grabbed my chest. In front of a large group of people, he exclaimed "You have an awesome body, it feels great!"
16. Four’s Company, Six Is a Crowd
My friend and I took these two girls in our class to our senior prom. We were all meeting up at a restaurant for dinner beforehand. We show up and the girls are sitting with two guys that graduated a few years ahead of us. At the time, we were just basically confused. We sat down and the six of us ate dinner. When we got to prom, the girls went in with us and the guys snuck in the back.
Turns out the girls just used us to get free dinner and prom tickets but brought their own dates.
17. An Unholy Alliance
I'm an atheist, and I mentioned that fact on my online dating profile. In my bio, I stated that I'm fine with religion but that it just isn't for me. Nevertheless, I go on a date with a girl from the site and she asks me what church I go to. I say, "Actually, I'm an atheist". And she flips her lid. "How the heck could you waste my time like this?? It clearly says I only want a religious man in my profile!"
From there, she goes into a rant about how terrible atheists are and how I'm going to burn in you-know-where. She was bad enough that the manager came over and asked us to leave. So when I got home, I started thinking that maybe I had her confused with another girl I was talking to. I pulled up her profile and there was literally no mention of religion anywhere. For her match's religion, she put "no preference". For her religion, it was "I'll tell you later".
18. He Shoots, He Doesn’t Score!
I went on a double date back in high school. It was me and my friend with two girls. We stopped by the local bowling alley and reserved a spot. The expected wait time was thirty minutes, so we wandered around and stopped by the two air hockey tables. For some reason, they were only about three inches apart from each other.
We decided to play. The girls played on their table and we played on ours. Theirs was a display of low-level motor skills that culminated in synchronized giggles. On the other hand, my friend and I were hosting an unofficial air hockey final. As we were going back and forth in full force, I accidentally chipped the puck.
The puck conveniently went flying to my right, nailing my friend's date square in the forehead. Annoying giggles quickly turned into annoying cries, and the girls ran off to the bathroom. My friend and I looked back at each other and instantly knew two things: 1) the date was over, 2) we had to finish the match. And so we did.
19. Scarred for Life
I once rode my bike for 17 miles on New Year’s Eve for a date, only to discover that my girlfriend already had other plans. I turned around. On the ride back home, I crashed and left a few large holes in my face from which I still have scars, five years later. I think it’s pretty safe to say that this was my worst date ever.
20. From Weird to Weirder
I had met this girl online. She was a friend of a friend of mine. We got to talking for a bit and we eventually decided to hang out. She lived about 30 minutes away from me in the middle of absolute nowhere, so I had to drive up to meet her. Since I was not familiar with the area, I asked her where she would like to eat.
She says, "Oh, well my favorite restaurant is not too far from here. We can go there. It's really fancy and expensive, though". I told her that I didn't really mind and that I was willing to go wherever. I asked her what the restaurant was called. She says, "Oh, it's Red Lobster". Now, I'm not one to care about how much money people have, but I was quite shocked that she thought Red Lobster was a high-class establishment.
However, I let it slide, because maybe to her Red Lobster is the epitome of fine dining. Turns out, Red Lobster is another 30 minutes away. On the way there, we passed a handful of other restaurants. Olive Garden being one of them. This is one of those details that gets dropped in stories very nonchalantly, like hmmm I wonder if this will be important later.
Anyway, we get to Red Lobster and the hostess is walking us to our table. She seats us, hands us our menus, and begins telling us about the specials. Before she is even able to finish, my date blurts out, "I already know what want!" It was so awkward. She didn't say it in a rude way, she more said it in a more excited way.
She said it as if it was totally awesome that she already knew what she wanted and everyone needed to know. Anyway, the hostess is stunned and just kind of walks away. Eventually, the waiter comes to our table, and she orders. She gets, "Shrimp Alfredo with no shrimp". At this point, I'm completely stunned and wondering what her deal is.
She made us drive 30 minutes, which is a long time to spend in a car on a first date, just for some fettuccine alfredo. Clearly, this was the best restaurant choice for that and not the Olive Garden. I still let all of this slide, because at this point she just seemed extremely eccentric and I thought that maybe if I got to know her better than her behavior would seem less odd.
After dinner, we are closer to my place than to hers and she wants to go back to my place to watch a movie. I oblige, obviously. We get back there and I ask her what movie she wants to watch. She picks Happy Feet. Yes, freakin’' Happy Feet. I guess at this point it's my own fault for even asking. So we start watching Happy Feet.
She wastes no time in starting to kiss me, so I don't make too much of a fuss. Now, the clothes are coming off to the soundtrack of Happy Feet. Really awkward. She starts talking about how great she is in bed. This was surprisingly not as awkward as it could have been, Happy Feet aside, and it was effective in keeping me interested.
Then she insists...no, demands that she remove my pants using only her mouth. Now, I can see how some people would be into this, but not me. I tried to talk her out of it, but she was convinced that she was going to be able to do it. And bless her heart, she did. Button, zipper, and all. It was still just a really odd thing to do. Especially on a first date.
Then, right when we were about to sleep together, she stops, looks up at me, and says, "I don't mess around with guys that are not my boyfriend. So ask me to be your girlfriend". So I did. We dated for about three weeks after that and she only got more crazy and weird from that point on. She actually got married a little while back, but before doing that she contacted me on Facebook to see if I wanted to have one more try with her.
I politely informed her that I would not be interested, to say the least.
21. Looking Out for Number One
I once had a guy tell me that he wanted to take me out to dinner and a movie for our first date. Before the movie, he said he was hungry and he went through a drive-thru. He ordered himself some food. He never asked me if I wanted anything. After we pulled out of the drive-thru, we sat in a parking space while he ate his food.
After he finished eating, he said, "Oh, sorry, did you want something?" Then, we went to the movie theater. We went to the concession stand. He again didn't even bother to ask if I wanted anything. He got himself a large drink. As we were walking away from the concession stand, he said "You can have some of mine". Gee, thanks!
22. Cat’s the Way I Like It
This happened to a lesbian friend of mine. It was a blind date that she had met through a personal ad in the local paper. This was before internet dating was a thing. My friend shows up at the woman's house. It's cluttered with all kinds of garbage and the woman talks nonstop like a speed freak, mostly about herself and her neuroses.
So they decide to go rowing on the nearby lake, and the woman insists on bringing her cat along on the boat. Yes, a furry, live house cat. Turns out she never went anywhere without schlepping the poor cat along. As weird as that seemed, my friend went along with it. She got through the date and never contacted this woman again.
Funny epilogue, though. Many years later, that same friend met her current partner. It turns out that her partner also once went on a blind date with the cat lady! We couldn’t believe it when we first realized this. Discovering that fact made us wonder just how many first dates this woman has been on. It really is a small world after all!
23. Down Under and Dirty
I'm Australian. My online dating profile said that I was Australian. I very clearly have an Australian accent. There is literally no way for my date to have not realized that I was Australian. Nevertheless, the very first thing that came out of my date’s mouth when we met up was, "I hate Australians". That date didn’t last very long...
24. Not What She Was Expecting
Ugh, I'll never forget this one. So a couple of weeks after my girlfriend had broken up with me and moved out, I was hanging out at the local handball courts when I met this young cutie. We set up a date and I picked her up in my fancy date pants and shirt. I took her back to my pad to watch some movies and we really hit it off.
She was admiring the pictures of me around my room and my mom was hardly intrusive at all. We got to know each other pretty well, so I did what any rational mammal would do: I presented my johnson and proposed we hook up. But get this: the girl just gets up and BOLTS! I guess we were not on the same page at all, and I just didn't catch on early enough.
25. A Previous Engagement
I once met up with a woman for a blind date and a little bit into our conversation, she suddenly got excited and asked me to congratulate her. When I asked why, her response made my blood run cold. She said, "I just got engaged last weekend!" Ummm, what??? Then what on earth are you here with me for?? I swear, there are some people whose brains I will just never understand…
26. Photo Finish
I was at my new boyfriend's house for the first time when I noticed a certain photo on the wall. I said "What? We have that same photo at home! Why do you have a photo of my great-grandmother on your wall?" Looking at me confused, he said "Because she is my great-grandmother!" I will never forget the shudder I felt when we realized what this meant...
27. He Has a Lot to Say
I once went on a dinner date with a guy who had dined at that restaurant before and complained about the food to me and the waitress before we had even ordered anything. He also interrupted me. A lot. Once, he interrupted me to improvise a commercial he'd been thinking about. His exact words: "I may not be a tenured professor, but I do love grapefruit".
Umm, what?? I’m sorry, but I have no idea what you’re talking about, buddy. We also shared no interests. So, naturally, he just talked about himself for the entire date. Awesome. Everyone knows that there’s nothing a girl wants more in this world than to spend an evening hearing about grapefruits and how great someone is…
28. All in a Day’s Work
I once went out with a guy I had met at a Christian youth group in high school. He took me to the movies, complained about how in love with my best friend he was, and then awkwardly tried to kiss me. He was a total weirdo. He stopped talking to me after that but started creepily hanging near my friends all the time until he graduated. So that was fun!
29. Going Out of Her Head
A dude who I randomly started a convo with at a cafe once asked me to go with him to an indie film screening the next day. Halfway into the movie, I developed a huge migraine and promptly puked into my soda cup. The poor guy had no idea how to react. Meanwhile, the old couple behind us started audibly laughing at us. Not exactly a pleasant experience.
30. Brotherly Love
I once met a girl on Facebook and went out with her on a double date. I brought my best friend along, and she brought her best friend too. Her brother was there when we met up to go see the movie. This seemed okay, as I thought he would just be there to check out if everything was okay. Then, it turned out he was staying to watch the movie with us.
None of this had been mentioned to me beforehand. I'm a very shy person and I find it hard to talk to girls at the best of times. Him being there made it nearly impossible for me to talk to her. My friend hardly said anything the whole night either. In fact, at the movie, he sat in between me and the girl. She apologized after the date about it, but we gradually stopped talking.
Not long after, my friend started talking to her on Facebook. They've now been dating for three years. Lucky me!
31. Putting on a Show
The worst date that I ever went on was the one where my ex-boyfriend took me to see a play about the women's liberation movement. Afterward, he informs me that the purpose of this outing was to give me confidence because he was planning on breaking up with me. I literally had no idea how to react. I had never experienced anything as ridiculous as that in my life.
32. Sushi Doesn’t Pay for Itself
I met a guy during college through some friends. He was good-looking, charismatic, and funny. After chatting the night away at a party, he asked me out on a real date. He picks me up in his nice car, but then immediately proceeds to take a phone call. He apologizes profusely, but says he "has to take care of something real quick".
He drives back to his house, runs inside, and then tells me he needs to swing by a friend's place. We pull up to this run-down house in a crummy part of town. He pulls out a baggie and a stiff magazine. He then begins weighing out an illicit substance on his lap. He then asks if I want to come in with him. I say no. He runs inside, comes back out, and then apologizes again.
We then proceed to get sushi.
33. Picture Perfect
I chatted, exchanged photos, and agreed to a first date with this girl I had met online. After seeing how different she looked in real life, most of the dinner was then spent in an active discussion over what a "recent photo" meant. We had to agree to disagree with her opinion that "any photo will do," and my opinion that "any photo more than ten years old will not do".
34. Sleep Tight
My worst date was with a guy who had recently been broken up with. We were already friends, so we just went to his house to watch a movie and play some video games. Right off the bat, he lays on the couch and goes on his phone. I have nowhere to sit and end up on the floor. He then opens his ex’s Facebook page and proceeds to show me pictures of her.
When he was done doing that, he fell asleep. I didn't have a car at the time, so I called a ride and played his video games while I waited. We did not have a second date.
35. Grunting and Groaning
I once had a blind date with this just painfully shy, rude, and aloof young Russian girl. I mean, I guess we just didn't click or whatever, but man she made it so darn awkward! She'd literally grunt in disapproval at everything I said, and she kept on complaining that she was so bored. When the waitress came back for the check, I blurted out "SEPARATE!" before she even asked.
36. Happy Birthday?
The worst date that I have ever been on would have to be the time when my date got completely intoxicated at my good friend's birthday party and then left with another girl. Yep, you always know you’ve chosen well when they can’t even make it through the first date without letting their attention wander off to other people...
37. Break a Leg!
My mother once went out with a 22-year-old when she was only 17. He took her to Burger King, then accidentally pushed her down the stairs to the subway. As a result, she broke her ankle and he had her walk home. Nine months later, I was born. I guess not every terrible date is just a giant waste of time!
38. Store-y Time
Years ago, I went on a first date with a guy during the daytime. We decided to go over to his parent's house to swim. On the way, we stopped at a 7-11 to buy some sunscreen. After I buy a bottle, we get in the car and this guy pulls a candy bar and a magazine out of his pants. He shoplifted from the store while we were on our date!
39. Sounds Like Someone Is Chicken!
I went out with a girl on one date and it wasn’t too bad. On the second date, we got chicken wings. She got really messy into them, sucking on the bones and slurping the juices off her fingers really loudly. When we were done, she did not wash her hands. Not even a little lemony hand wipe. Nevertheless, throughout the night, she kept reaching out to touch my face—but that’s not even the worst part.
Not in a gentle caress or anything like that. Her hand would just shoot out and pinch my cheek or grab my nose. Her hands left little sticky marks all over my face. I started to flinch whenever she moved. Finally, later in the night, she went to the bathroom at some place we were at. I thought she would finally wash her hands, but when she came out she grabbed my hand and hers was still sticky.
40. Leaving So Soon?
I once went on a date that seemed pretty decent in and of itself. Then, after I went home, she continuously hung out in my parking lot for over two hours after she dropped me off "in case I changed my mind about doing something after dinner". Umm, if the answer to that wasn’t a definite no before, it certainly is now...
41. Pay to Play
My worst date was the one with the girl who openly told me that the only reason she was dating was to find someone who would pay her rent and pay for her kids as well. She even directly asked if I was up for the challenge. Needless to say, it didn't work out for her. You gotta give her some credit for her honesty, though!
42. Home Sweet Home
Many years back, I met a really cute guy at the local handball courts. We exchanged information and decided to hang out the next day. I got all gussied up and he picked me up in the same clothing he had been wearing at the park. That was a red flag right there, but I decided to give him the benefit of the doubt. Maybe he had many pairs of the same sweats? Guys always have lots of white tee shirts, right?
So, we started driving and I asked him what the plan was. You know, like where we were going to go. He tells me that he is kind of low on cash right now, but thought it would be fun if we went back to his place and watched some movies. See, now I know what that means, but as a 16, 17, or 18-year-old—which I was, I can’t quite remember—I thought, "Oh alright, he is older. Maybe he just had to pay rent or something".
As I looked into his big green eyes. I half-heartedly agreed with his suggestion and we headed over to his place. I walk in and he begins to tell me that he lives with his mom and that his ex-girlfriend had moved out a while back. He takes me up to his room, and I am immediately taken aback. He has pictures all over his bedroom of himself and his ex-girlfriend.
I understand that this is like the third red flag, but I begin to rationalize this by saying to myself, "Aww, he is so heartbroken about his ex-girlfriend that he can’t bear to take the old pictures down! I will heal his heart!" Yeah, I know I’m stupid. Anyway, we start talking as he puts some movie on. He then asks me three questions about myself.
As I begin to answer question number three, he stops me and says, "I have heard and learned enough about you. I really like you and I think it's time for us to sleep together". He proceeds to take out his private part, flops it out in front of me, and casually points at it. I immediately get up, grab my bag, and run out of there as fast as I can.
As I look back now and reflect on the whole bizarre experience, I know that it was a stupid move for me to have gone back to this sketchy guy’s place right after meeting him for the first time. I also realize that many terrible things could have happened to me, but teenagers are stupid. I'm just glad that I am alive to tell the tale and share it as a warning to others.
43. That’s a Pass (Out)
I once had a girl beg me to take her out. I can't drive, so she had to pick me up and we went to this restaurant on the other side of town. Everything seemed to be going fine. I had her laughing and was telling her a bunch of interesting stories. She had my attention the entire time as well. She was far from boring. Then, just when I finished eating, I suddenly had a terrible feeling.
I started to get light-headed. This is very rare for me, but it had happened before on occasion and I knew what was going to happen next. Before I could warn her, I passed out at the table. I fell to the floor. When I came to, she was gone and the owner of the restaurant was hassling me to pay the bill. I paid the bill and walked the 11 miles home alone.
I tried calling everyone I knew, but no one was answering their phones. There's no public transportation in our area either. I ran into her a week later. Curious as to what her excuse would be, I asked where she got off to that night. She called me a freak and asked me to go crawl under a rock and disappear. That was pretty much the last straw for me. I gave up on finding someone to be with.
44. Falling Behind
A few years back, there was this guy who I knew and liked. He was handsome, a little older, and fun to be around. Let's call him "D". So one day, "D" calls me up and asks if I want to come and hang out at his place. I agree, and "D" says "Cool! Just so you know, I have a few friends over and we're smoking right now, but they're leaving soon so come on over and we'll see where the night goes".
"Not a problem," I say. I've partaken in that activity from time to time in the past, so it certainly wasn't a deal-breaker. Well, I show up and his friends are still there. Again, not a problem. When it comes to just hanging out, the more the merrier! So as I sit down, I find it odd that I don't smell anything like I was expecting to smell. When I realized what it was, my blood ran cold.
Sure enough, it turned out that when they said "smoking," they didn't mean the light stuff. They were using extremely dangerous substances. So, I politely declined to participate and began to contemplate my escape. "D" and I started to chit chat and I noticed that he was not participating either. So, I thought to myself, "Great, maybe his friends are users, but it seems like he's not into it".
A small time passes, and it stops feeling awkward that people are doing this around me, especially because the host and I aren't partaking. "D" then calls me into the other room and closes the door. He proceeds to start kissing me. Given that we had made out in the past, it wasn't that unexpected or a big deal. "Finally!" I think to myself, "The night is going somewhere!"
Well, as soon as I get that thought out, he pulls down his pants. Ooookay? Forward, but not necessarily unwelcome. He pulls away from me and reaches into his dresser drawer. From there, he proceeds to pull out a piece of tin foil filled with a huge sample of the hard substance. "Hold this," he says, before grabbing some lotion. He then shouts: "Shove this up my butt! That’s the best way to use it!"
I don't remember exactly what my reaction was or what exactly went down next. All I remember is being sure that I was not interested in following that instruction. I seem to remember saying that I was allergic to the lotion. Smooth, I know. Then, I remember pretty much running out of there like a sprinter after saying my abrupt goodbyes.
45. Standing on the Corner
I asked a girl out in late spring, so we decided to walk around outside. It was nice out and she went to a different school than I did, so she showed me around campus for a while. It was pretty interesting. She was probably slightly out of my league, but I thought things were going well. We decided to grab a bite to eat at a place in the nearby bar district and sat outside.
Halfway into the meal, a local wanders down the street playing a harmonica and just rocking out. We barely even noticed him because things were going pretty smoothly. We had just discovered that we enjoyed the same kind of music and were deep into a conversation about that. Then, all of a sudden, we hear a lot of shouting and swear words.
We look over to see that another local man had appeared on the scene, angry at the first guy about who owned that particular spot of the street corner. The fight got pretty heated. We tried to ignore it, but it was slightly impossible as they were only about ten feet away from us. I still can’t believe what happened next. All of a sudden, the second guy pulls out a knife and stabs the first guy in the neck.
He passed really quickly and blood was everywhere. It was horrific to witness. We were then questioned by the authorities and had to make statements and everything. It basically ruined the entire evening. Somehow, I got one more date out of this girl, but we just struggled to make conversation at that point. After witnessing a murder, things were just really anticlimactic.
46. Fourth Quarter
In high school, I took this girl out to dinner and a movie as a first date. It was mostly as a courtesy to a friend, because this girl would always be the third wheel on all of their dates. We finish up the movie and I am driving her home when she says to take a turn here and there to make it back to her house. Turns out, she had decided that it would be prudent for me to meet her grandparents.
This is fine enough with me, as I tend to have an easy time mingling with the golden oldies. However, it is about 10 minutes before her curfew when we arrive at her grandparents’ house. Before we even walk in, I tell her to call her parents and let them know why we are running late. She puts up a fuss and says they won't care and that I shouldn’t worry.
Time goes by, and we end up at her grandparents’ place for an uncomfortable 30 to 40 minutes. All the while, I am telling her that it is past her curfew and that her parents don't know we are there and she should let them know. We eventually make the 15-minute drive back to her house and I am feeling completely uncomfortable the whole way there.
The moment we arrive, her mother rushes her into the next room and some mumbled yelling occurs. I'm sitting at a table when the father comes into the house and gives me an angry look before yelling some more. This is all a bit much for me, but I handle it okay and go home. At this point, I’m just glad to be leaving and not even thinking about what could be coming next.
As soon as I walk into my house, within my curfew mind you, my mom starts yelling at me, "WHERE THE HECK HAVE YOU BEEN??!!" I'm immediately wondering what in the world is going on. Well, it turns out that, while he was waiting for us to return, the girl’s father drove to my house and started banging on the door and yelling at the top of his lungs.
Apparently, he was shouting that I have his daughter and that he wanted her back. My mom doesn't know who this man is and, in the panic from beyond the locked door, she heard his shouts as, "YOUR SON HAS GOT MY QUARTER! YOUR SON HAS MY QUARTER AND I WANT IT BACK!"
My mom freaks out, thinking there is a psycho at the door. She grabbed a weapon and called my uncle from across the street. My uncle also grabbed a weapon and yelled at the guy from across the road to either leave or that he was going to get shot. Meanwhile, my mom is politely yelling back through the door, "IF MY SON HAS YOUR QUARTER, HE WILL GIVE IT BACK TO YOU TOMORROW!" to try to appease him.
The guy eventually leaves, but not before my mom becomes completely terrified and confused about what she had just witnessed. I finally explain the situation to my mom and convince her that the girl’s family is crazy. She breathes a sigh of relief and we both have a good laugh about it later. However, this has to be the WORST DATE EVER!
47. Father’s Day
It was grade 11, and I had just moved to a new town. I quickly became attracted to this one girl and would've given anything for a date with her. We got paired up to be partners in our "Food and Fabrics" class, and I totally pulled out all the stops. I was doing whatever it took to get a date with this girl. It was all I cared about.
In the class, there were a couple of projects where you would have to sew a pillowcase or a pair of pajamas. My family didn't have a sewing machine, so we would do the projects at her house. Upon these visits, I began to question how badly I wanted this girl. She lived in what appeared to be a wood cabin, and her father seemed legitimately insane.
The walls were lined with animal skulls, the guy was a devoted hunter. He had bear-skin rugs and antlers all over the place. He would always walk around with his shirt off, drinking a Budweiser, chewing snuff, carrying a deadly weapon. He never spoke a word to me. The whole experience of being in that house just felt extremely weird.
By this time, I was starting to gain some friendships in the school, and one of the guys I met named Neil noticed that I'd taken a liking to her. He then asked me if I'd heard about her parents—and let me know the jaw-dropping truth about them. He proceeded to tell me that her father had taken her mother’s life and gotten away with it. Her body was found in the middle of town, pumped by a couple of rounds from a weapon exactly like his.
He got off on the charges due to a lack of proof, and the girl had to live with him because he was her last living relative. At this point, I was like "What in the world???" The story made no sense, and I wasn't about to believe it. It definitely kinda rattled me, though. But there was no way that I was going to bring it up to her.
Anyways, a little time passes, and I ask her out. I go to her place to grab her, and she's gorgeous. Her dad makes a comment about, "You know what'll happen to you if you touch her," and suddenly the story is the only thing I can think about. We went skating, then to a movie, but I was terrified the whole time. I just couldn't get the thought out of my head that her dad was going to attack me when we got back to her place.
So, after a sub-par date, I start the long drive back to her place. We get to the end of her driveway and she gets me to park and turn off the lights. She wants a kiss. At this point, I forget all about her dad. I lean over, and put some moves on. After a few minutes, we stop and I turn the lights back on. There's blood in the snow at the end of the driveway.
I wanted to say something when I noticed this, but I didn't want to sound like a scaredy-cat. Her dad was a hunter, right? I'm sure there's a logical explanation. I put the car in drive, and start the winding trek down her driveway. The trail of blood seems to be getting thicker, and I'm getting more freaked out with every passing second. She still says nothing, as she's fixing her hair in her mirror.
I keep driving. More blood. I turn the last corner of her driveway, and see my headlights shift from the trees to her father. Standing in the middle of the driveway. Covered in blood. Blood all around him. Huge knife in his hand. And what appeared to be an undressed human body lying at his feet. I start hyperventilating. Suddenly, I'm crying, and don't know why.
I pee my pants right in front of her. Her dad takes me to the hospital. Turns out I have had mild-asthma for my entire life and had a panic attack that triggered it. Apparently, the dad had found a bear at the end of the driveway, shot it, dragged it down the driveway, and skinned it before we got back. But that’s not even the craziest part—the girl’s mother was still alive and lived just a few blocks away! That guy Neil totally wound me up.
Once we cleared everything up, everything somehow turned out okay. This happened a little over three years ago and I’m still with the girl. Her dad makes fun of me all the time, except we've gone on hunting trips together and I'm pretty sure he's secretly a fan. Neil was just a jealous ex with a wild imagination. Her parents had simply split up. And her mom turned out to be pretty awesome too.
48. This One Gets Bad Real Fast...
In 2005, I was on OkCupid and met this guy who seemed smart, interesting, and funny. So we chatted a bit online for a few days and then met at a coffee shop. All seemed normal and well, and he seemed like a nice enough guy. A week later, he invited me out for dinner. We had dinner, and it was all normal and fine. Nothing to complain about.
Again, there weren't exactly fireworks, but I wasn't put off by him or anything, either. There were some things that now I know are warning signs. He made strange comments that, looking back, were really kinda crazy and woman-hating. For example, he kept making insulting remarks about women in the restaurant. Things like, "She's dressed like a loser," "I bet those knockers are fake," etc.
Anyhow, he sent me a message a few nights later and asked me if I wanted to come over and hang out. I didn't have any other plans that night and I was bored. He lived about a mile from my apartment, so I walked over to his house. I didn't have plans to sleep with him and the extent of the physicality of our relationship up to that point had just been a couple of hugs.
When I arrived, it was clear to me that he had been drinking. He wasn’t fully intoxicated, but he was certainly on his way there. He offered me a drink and I declined. We hung out, listened to music, and even played some music together since he was a musician and I like to tinker. We also talked a whole lot and everything was generally going okay.
Then, he starts telling me crazy stories about his life. He told me a bunch of personal stuff about how he had been mistreated by a relative as a child, how his best friend in high school had lost his life in a car accident with him in the car, how his mother was schizophrenic, etc. Then, he starts talking about how lonely and sad he was and how long it had been since he had met a woman he liked.
He told me how much he liked me, how attractive he thought I was, and how much he wanted to sleep with me. We had cuddled and kissed a bit earlier in the night, but I was not interested in going all the way with this dude right then, especially knowing that he was intoxicated and acting a bit strange. Nevertheless, he started coming on to me really strongly and grabbing at me.
I moved away and tried to tell him I wasn't interested when he literally started begging me to sleep with him. He was whining and pleading and begging, telling me he'd do anything I wanted. I really had no idea how to react. This had never happened to me before. I felt really uncomfortable and should have left right then, but I felt bad for him.
He was clearly damaged and intoxicated. I tried to tell him that I liked him but didn't want to sleep together right then. I made some comment about how I needed to leave soon, when he suddenly grabbed me by the waist and pushed me down on the ground. I had been sitting on a couch up till that point. He reached down and tried to pull off my pants.
I ran out of his house as fast as I could and sprinted all the way back home. It was the weirdest experience of my life, man. He never contacted me again; but a couple of years later, I ran into him at a bookstore. He looked at me and started walking towards me, like he was going to talk to me. I immediately power walked out of there.
49. The Cards Were Stacked Against You
I once took a girl out for lunch at a small little Chinese place. The food was pretty mediocre, so I didn't really think much of it. I take out my card so I can pay, and the waitress informs me that they don't take cards. I froze up. "Holy cow, what do I do??" Well, being the brilliant guy that I am, I asked my date to go get money from an ATM to pay.
As she was out, I thought I really just blew it. There was no way she was going to respect me again after I failed to pay for her meal. But to my surprise, it turned out she was laughing the entire time she was at the ATM and thought the whole thing was adorable. I got a second date. That time, we went to a REAL Chinese place that took cards. We ended up dating for almost four years.
50. Fire and Ice
First date. We went ice skating. She fell. I accidentally skated over the back of her hand. The blood on the ice was a sight to behold. She wouldn't speak to me as they put her onto the stretcher and took her away. The last I ever saw of her was as the ambulance doors closed. Needless to say, I did not get a second date.
Sources: Reddit,
