Do you have any weird date stories? Or hilariously awkward romance stories?
Maybe you went on a blind date that went terribly wrong?
Or you were dating somebody that just didn’t get you, even though they were trying to be s*xy?
AskReddit users were nice enough to share their most cringeworthy experiences for your reading pleasure.
1. Two tales
“I will tell about both worst weird, and best weird because, I can’t really pick one
Worst weird was this guy that was an avid hiker like me, and suggested we do a quite easy, very known and travelled circuit by the coast. The weather was great ( sunny, windy, the very best for a hike) but.. The guy spend the three hours of the circuit reciting BY HEART all the people who offed themselves on the path and he knew.
Just. So. Many.
I mean, it was odd at first, creepy soon after and quickly descended into terrifying.
Needless to say no second date was had.
Weird cute one was with a guy I dated for some time after: we were just sipping coffee on a bench when his phone went off : his brother’s wife had gone into early labor and said brother was freaking out, and in his soon to be a dad way ahead of plan frenzy, shouted: ” the baby’s room isn’t even painted!”. Cue my date leaping in with a ” I got this, stay with your wife!” , pocketed his phone, turned to me and went ” I have a double of his keys.. wanna help me paint the room ?”
“What, like, now?”
And we spent half a day painting a kid’s room. That was fun, all things considered!”
2. Relationships are hard, but not every day.
This is morbid but I thought it was normal to argue every day. I thought ‘all couples have their bickering’ and it was just a regular thing.
I was astounded when I went into my next relationship and actually got on with the guy and went weeks and weeks without having any issues.
It always felt like the bubble was going to burst.
Goes to show – don’t stay in a relationship just because you’ve already invested a tonne of time.
You get one life, spend it with someone who makes you laugh every day.
3. That’s pretty gross.
“Had an ex who thought that it would be hot to surprise me by getting Hershey’s syrup, whipped cream, and a banana to make a sundae IN HERSELF.
Do you want yeast infections?…because that’s how you get yeast infections.
She got a yeast infection.”
4. Sounds a little unhinged
“So many adventures, so I’ll stick with the highlights. Dinner seemed to go all right, except that he drank most of a shared pitcher of margaritas by himself, then drank all the booze I had at home. I was kind of irked, so we go searching for more.
The first place was closing up (it’s Sunday), so he goes up and bangs on the windows, loudly demanding that they sell us some brews and calling them a**holes while I die of embarrassment. At the next place, after they served us, he casually said, “Oh yeah, I don’t have any money, so you’re going to have to get that.” (Not that I expected him to pay for my brews, but he expected me to pay for for his.)
In conversation, he mentioned that his favorite book was Ulysses and compared himself to Jack Kerouac. I asked him what kind of movies he liked, only for him to snottily retort that he watches “films.” He had me read a short story he wrote that, frankly, was pretty terrible, but when I offered polite criticism, he got angry and said I just didn’t understand. That was the problem with being a “natural writer,” he said. No one understands.
At one point during the evening he wanted to check on his dog. He said it wasn’t far, but it turned out to be a long drive to the middle of nowhere. Nothing was open, and I had to wizz really bad. It was the most resentful roadside pee imaginable.
After he snapped at me about not understanding his writing, I said I was tired and he should go. He asked me for $3.00 for gas. I wanted him gone so much I actually gave it to him.
I later found out that he had a huge coke problem, and he told the mutual friend who set us up that we had s*x that night but that I ghosted him after. The ghosting part was true, anyway.”
5. Still enjoyed it.
“My girlfriend when I was 16 tried to give me a lap dance while I was editing her English paper.
She threw her head back and broke my nose.
At 16 that was still kinda hot.”
6. That’s creepy.
“After a long week of exams, I came home to take a nap before we went out for the weekend.
My ex lied to my roommates to get a key to the place and proceeded to watch me sleep for 4 hours to make sure I wasn’t “disturbed.””
7. That is painful.
“There was this guy that I was making out with, but I was bent on not letting it get serious. He was handsome, but he was way too cringe.
So one night, he texts me to come up to his dorm, and I’m expecting the usual make out session.
When I arrive, he greets me at the door. Candles glittering like a godd*mn Toni Braxton video. We weren’t even allowed to have candles. He picks me up in bridegroom pose and whisks me over to his twin bed. All the while, his poor roommate is hunched over his computer in the corner with his headphones on, just pretending that this is all not happening.
The guy proceeds to play me a song he wrote on his acoustic guitar and sings to me with tears in his eyes. I just kept glancing at the roommate for some intervention, but nah, he wasn’t having it.
When he finishes, he puffs his chest for courage and confidently declares his love for me. There was a long, cliffhanger of a silence before I said: “I’m sorry, but I don’t feel the same.” That was about the time he literally ripped off his button-up shirt in some display of brute strength and started banging his head on the wall, sobbing and murmuring about being pathetic. I actually walked over and used my hand as a cushion between his forehead and the wall to get him to stop.
Meanwhile, his roommate never acknowledged what was going on around him. Not even once.”
8. You’re going to love my mother.
“For Valentine’s Day one year my ex-husband got me a full body massage…with his massage therapist mother.
One hour of straight cringing.
The most unromantic time I’ve ever had.
But, yanno… at least it was cheap!
9. Ugh! No way!
“Bought me one praying mantis egg because she thought it would contain one praying mantis.
It hatched in my room and there were like 500 babies eating each other and crawling everywhere, since they were small enough to fit through the vents in the bug cage.
Now, I do like bugs. But I don’t like 500 bugs all trying to eat each other.
That was completely an absolutely disturbing.”
10. Totally hammered.
“My now-husband, after a night of drinking in college, decided he would sneak into my dorm room (I had to work the following morning) and kiss me awake and we’d have some s*xytime.
He completely overestimated the level of suaveness he could pull off while plastered. He makes it through the door without me hearing, but I wake up to a naked dude crawling up my body from the bottom of my twin bed. I screamed and shoved – as one should in such a scenario – and he ended up on the floor, where he very nearly passed out.
About this time, I realized who it was, got his naked butt up off the floor, closed the door after assuring my sleepy neighbor that he was fine, and shoved him into my bed. I got into bed, and he attempted to crawl on top of me, mumbling something about how s*xy I was in the middle of the night. It took two “Go to SLEEP, [VandyBoy]”s before he finally rolled over and passed out.
He had no idea the next day how he’d ended up in my bed.”
11. It took you two years?
“Went over every inch of my face like a blind man reading Braille. Something about being able to better remember me later….
And instead of kissing me on the cheek or forehead, he would kiss under my chin, like, directly beneath my tongue…because “it was a space no one else had ever kissed” or something.
Took me 2 years to realize how crazy he was.”
12. Very, very sensual.
“My ex girlfriend got turned on by the romance languages and heavy accents.
Luckily for her, I took 4 years of Latin in middle and high school.
Unfortunately it’s not really a speakable language, however I memorized a few things for class assignments.
I seductively whispered the pledge of allegiance and the opening paragraph of the Caesar’s Gallic w**s in her ears more times than I can remember.”
13. How truly touching…
“A guy I went out on a total of one date with.
We were at Burger King (yes, I know, how romantic to begin with), when he saw a fly on the window next to our table. In a display of his big strong manly man-ness, he used his bare hand and smashed it against the window.
Upon seeing me disgusted, he decided that, to make it better, he would just smear the guts into a heart shape on the window glass.
How truly touching.”
14. Wow. Bold move.
“Came into my house last night and found a stuffed elephant sitting on the table.
While I’m contemplating why the F there is a Babies-R-Us elephant on a plate, my now fiancee says from the doorway “I think it’s time we address the elephant in the room” and dropped to one knee with a ring box.
I’m still giggling over that one.”
15. A classy guy.
“I was dating my current girlfriend in high school. Senior year, prom season came around.
In order to ask her to prom, I wrote “Prom?” on my a** and mooned her. She cried, clearly expecting something more romantic.
I still feel bad about it to this day, but we laugh about it now.”
16. Not all expectations are bad ones.
I see so much horrible things on here, mine is quite tame but here goes.
My first boyfriend would always leave me small presents or notes underneath my pillow if I had to get up earlier than he did.
He was quite romantic and told me I love you quite a lot.
When I got a new boyfriend I caught myself looking underneath my pillow for at least a month/2 months in, just out of habit.
17. You can’t make anyone else happy.
My ex put her happiness on me making it my responsibility.
Would demand I stay around and cut my work hours back and then be upset when we wouldn’t have money to go out. Every time I would try and leave I was coerced with s*x to stay, because I was young and stupid. After 8 years I had enough I moved 5 states away.
Had a chain of bad relationships that ended, took some time to work on myself and I’m now engaged to an amazing woman I can communicate with share feelings about issues and who values a healthy relationship.
18. I guess it’s how garbage men are.
I have a physical reaction now when my current partners are nice to me when I do something he would have berated me for hours and locked me in my room for. Like, I get a panic attack because my partners are nice to me when I drop a glass, or got laid off, or forgot to unload the dishwasher. And then they don’t bring it up every time they’re irritated with me. My ex was still yelling at me 14 years later for s**t I did when we first started dating – s**t like I forgot to pick up his laundry from the floor or bought the wrong brand of bacon. At the end there, the lectures lasted hours as he recounted 14 years of offenses.
My current partners? They don’t throw s**t in my face that I did the day before. The dissonance is crazy.
I knew the other victimization wasn’t normal, but my step dad is the same way with my mom, so I had no idea, I just thought it’s how men are.
19. Not everyone’s love language is physical touch.
That some girls, in a relationship, don’t like to kiss as often as others.
I’m just talking about pecks when I/gf gets home etc.
I always enjoyed a hello kiss but I guess some girls don’t?
20. I’m emotionally spent just reading this.
Being cowed into an “open arrangement” = normal.
Him introducing me to “friends” while hanging out or going to parties and then him telling me later in the evening after the ice had broken that they were actually the girl(s) he was Fing. Capitulating to his insistence that we continue to hang out even though I was uncomfortable with knowing this new information. = Normal.
Him making unwelcome and uncomfortable comments to other women I was friends with in front of me to attempt to orchestrate threesomes that I was not ok with.= Normal
If you love me, you’ll chase after me = Normal
If you love me you’ll leave face time up at all times so I can see whats going on in your dorm = Normal
If you love me you will not show any sad or mad emotion because it ruins my mood = Normal.
21. Everyone’s libido is different so she probably wasn’t rolling you.
She made me believe the old TV tropes of women NEVER wanting s*x.
I had to work my a** off to get her to give me some action.
The next girl I had was just Fing amazed that I didn’t just ask for it when I wanted it.
The bewildered look on her face when she finally asked “You realize I’m wet too right?”
22. When they can make you believe anything they want.
My ex basically taught me that it wasn’t okay for me to be upset about things.
Every time I would get my feelings hurt (even when I was upset about something completely unrelated to him) it was somehow flipped around so I ended up reassuring and comforting him. That s**t really messed me up, and I basically had to relearn how to be vulnerable with my SO.
He also had a very solid plan of how he expected me to live my life, basically his main goal for me was to have kids and be a good housewife.
On the bright side, nowadays I’m happily engaged and my fiance treats me with so much love and respect.
He’s supportive of my dreams and we are able to lean on each other in times of hardship.
23. What a fantastic moment.
I texted my then new girlfriend about where I was and who I was with about every 30 minutes.
After the 3rd time, she told me that she didn’t need to get updates on what I was doing, and to just let her know when I got home safe. I remember feeling almost a physical weight being lifted off my chest because I didn’t have to worry about my girlfriend freaking out if I didn’t update her.
I learned what trust felt like that night.
24. I know this isn’t funny, but maybe it will be someday.
That every time was essentially a quickie.
Almost a whole decade of nothing but 5 thrusts and then blast off.
After that relationship ended I felt like Jasmine on a magic carpet ride….a whole new world.
25. This sounds like it’s going to work out.
It wasn’t super long term, only about a year but when you’re in high school that’s fairly long term.
My ex was a very clingy dude, sweet but would follow me around every social gathering and get jealous of me spending time with my friends. When I started dating the guy who is now my husband I remember looking around at a party early on of mostly my friends that he hadn’t met before and I couldn’t find him. I asked someone where he was and he was out by the fire with a group of people chatting and hanging out.
I was astonished that we could just go our separate ways in a social setting and that was totally fine, we didn’t have to be attached at the hip the whole time.
26. This is so depressing.
Pr0n is not a documentary.
Being used as a s*x doll, contorted into uncomfortable positions, and pounded until you bleed, can’t stand up, or just break down crying from the pain isn’t normal.
Nor is a**l s*x a necessity. We were both virgins and he had major pr0n brain.
I thought I was bad at s*x and would never be able to have a positive experience with intimacy until I finally left him and was with my second boyfriend.
I’m ok now, but wow was that a horrible person to lose my virginity to.
27. He knew she was a keeper
“Probably the 2nd date with my now wife.
Some guy paid me to get revenge on a buddy of his and wanted me to scatter a few hundred pounds of potatoes into his buddies front yard.
It was near where I was planning on taking my now wife and she said she would be cool with helping.
So we drove to this guys house, made sure he was not home, filled his yard and driveway with potatoes together then went on our date.”
“Met with a girl in a dark university bar. Everything is going well. We eventually go outside because there is a mechanical bull we are goin to try. As soon as she gets on the bull, I realize she is at least 10 years older than she claimed and has a rotten m**h tooth. After asking her a few questions, she admits that she has two kids outside of the state and has no interest in them.
She also admits to having a girlfriend with whom she is not s*xual. She is physical with her though. She starts showing me pictures of her girlfriend with bound breasts…like ropes around them bonding them. This girlfriend of hers is white, but her breasts are black from being beaten in while bound. I was young and completely unprepared for this. We ended the night early and I even got the courage to tell her I wasn’t interested instead of ghosting her like I truly wanted to do.”
29. Meet my father
“I went on a date with a guy named Dan when I was in my late teens. Dan said “I’d like you to meet my father, he’s going to love you”
So I got in the car and as we started heading out of town I asked where we were going and Dan said “you’ll see, we’re almost there”
15 minutes later we pull I to a cemetery and he says come with me, I was nervous as I followed him down a little hill and he kneeled down in front of a tombstone and said “dad, she’s going to be my wife someday”.
That was the first and last date Dan and I ever had.”
30. Don’t tell anyone you’re a mechanic
“I have a bad habit of telling people I’m a mechanic too early into knowing them because I really enjoy it and I like talking about it. The last date I had involved about 20 minutes of us actually talking to each other about things like school, what books we’re reading, and video games. When we get to the part about what we do for a living, I tell her I’m a mechanic. She immediately drops all conversation and begs me to go fix her car right then and there.
I’m a little too nice of a person and couldn’t say no at that moment, so we pay for our drinks and leave. As soon as I see her car I know I made a mistake, it’s been recently wrecked and should not have been on the road. She then starts to tell me about how a friend of hers says it only needs a few repairs and it should be good to go, when in reality it probably should have been totaled with how bad the front end was caved in.
I tell her this and she starts yelling at me saying I must not know what I’m doing, then says I need to fix it anyway and that she needs to borrow my car to go run some errands at 10:30 at night. I tell her no, and that I’ll call her a tow truck since I have AAA, and that I don’t think we’re going to work out. It’s been 3 weeks since then and I still get calls from her asking her what’s wrong with her car.”
“I essentially got cat-fished by a coworker. There had been some mutual attraction months before but I decided it wasn’t a good idea and told her we should just be friends. Then she made a fake online dating profile, used her knowledge of my likes/dislikes to attract me to this profile, carried on extensive communication pretending to be someone else, and then showed up to our date expecting me to suddenly fall head over heels in love with her.
She showed up at the date and I asked her what she was doing there, she replied “I think you know why I’m here” and I got in my car and left without saying anything. Eight years later and her cubicle is still 15 feet away from mine.”
32. A whole series of them
“Mine is a series of dates that led to the weirdest one.
I was a student at a big state school and it was very possible to meet someone at a party and never see them again. I chatted with a woman a few times who was always interesting and engaging. She was a Christian and outspoken about her faith. I’m cool with that, but I’m not all that outspoken myself.
I asked her out to dinner and a movie after the second or third time of running into her and chatting and she said yes. I wanted to keep it traditional and do the whole date thing, so I cleaned up and picked her up to go to a restaurant and a movie. It went well. We hugged, said our goodbyes, and that was it.
We wound up going out again for a drink or something and things seemed to go okay a second time. It was sort of platonic, but we never had a conversation where we said that we were just going to be friends or something else. In either case, we were definitely going on dates.
So, I invited her out on my signature move- a canoe trip on a local river. It’s spring-fed, crystal-clear, and there are a number of deep springs with floating docks. It’s a great time. We both worked retail and had a day off in the middle of the week so that was the plan.
When she got in the truck, she was surprised to hear that she would be needing a bathing suit to go canoeing (?) and so we stopped at Target for her to buy one. I received specific instructions to stay in the truck while she shopped. No big deal.
When she got back to the truck, she let me know that she bought a two piece because all of the one piece bathing suits didn’t work. Awesome. Things are going swimmingly. Except she followed up with “it doesn’t matter. You will never see me in a bathing suit anyway.” That was weird, but okay.
The canoeing was fun. We swam. She swam in a T shirt. That was weird. But, overall, we had fun. On the way back to town, I asked if she wanted to order a pizza and watch a movie. She said she couldn’t, because she and her roommate had a policy that boys were not allowed over alone. Then she backed up and said that well, since these weren’t dates and we weren’t dating, that it would be okay for me to come over, but I had to leave by 9:00.
Hold up, I said. These are dates. She got all weird about how these weren’t dates, that we were just friends, and that she was not going to date. God would provide her with a husband on his accord. Right, I said. And these are dates. I’m not sure how you missed that.
She went on to talk about dating and marriage and then dropped that she knew I wasn’t the one because God told her that her husband was a baseball player. She knew that her husband was going to be a baseball player and she would consider going on a date with a baseball player, but it would be a stretch.
I rescinded my offer to watch a movie and order a pizza, and that I didn’t think I was interested in going down this road. Shortly after, she called my phone about a dozen times in a row because she had a flat tire and wanted me to come change it. I told her to check with the baseball team.
Epilogue- Some time later I was at a party, standing around a keg, and doing normal college student stuff when one bro asked another bro if he remembered to invite his girlfriend to the party. People in the know laughed and eventually the story came out that this random girl would come to every baseball practice and every baseball game by herself, stare, and pray. She’d try and interject herself in awkward and creepy ways and she would randomly show up wherever they were. This was pre-social media, so it had to have taken a lot of effort to make this happen.
So, there you go. Don’t not date crazy religious women who are betrothed to collegiate athletes.”
“Once had a girl get up and go to the bathroom during a make-out session. Came back with her head shaved.
I asked why she did that, she told me her “head was too hot” and she “had been thinking about doing it for a while”
Made out for a little while longer until I could think of an excuse and got the heck out of there.”
34. Oh my
“I’ve got a weird one
met a girl at a bar
went back to her place
she did the whole whipped cream bikini thing
the whipped cream was spoiled
I muscle through sour whipped cream
30 minutes into fun time her daughter walks in on us that I didn’t even know was there or that she even had kids
another 15 minutes and her Aunt & Uncle walk in on us… yeah- wasn’t even her house but her Aunts.
She then breaks down in tears and starts telling me about being brutalized and her old h-train addiction.
then proceeded to tell me about her 2 other kids
I nope right the F out of there
a week or so later I see in the newspaper that she was in a car accident and passed.
surviving family members in the obituary included her current husband.”
35. Getting back out there
“First date after a broken engagement for me.
This girl kept telling me how much she wanted to go on a date with me off tinder. I was hesitant but she was persistent. Well, we got to the coffee shop and had some really nice conversation. Then she said she had some coworkers down the street that were at the Arcade Bar playing in a Mario Kart competition and if I would like to join in? Yes! We went down, got some brews and met the coworkers, super cool dudes.
She spent the rest of the night dodging around the bar trying to avoid them. Kept telling me how weird it was that they were here… uhh yeah but this was YOUR idea girl. Then she went to the bathroom and as she was getting up looked and me and said,
“can I bring my brews or are you going to drug me?”
Me “Uhh, what?”
“Are you going to drug me?”
“No, why the heck would I do that?”
“Ok.” Gets up to leave… “Actually, i’m going to bring my brews.”
Then when she gets back..
“My mom isn’t going to like YOU.”
Me “Uhh, ok why not?”
“You have me drinking on a Thursday, I never do this. I can’t believe you made me.”
me “All of this was your idea, every single thing about it!”
Then when I walked her back to her car, she sprinted the last block to her car, got in and drove off. Then texted me telling me what a great time she had and if we could set up a time to meet again.
“I was on an exchange program with a French school and matched with one of the girls in my class on tinder. We didn’t speak before but we made an appointment via messages to meet at her place to watch a movie.
We then realized that I didn’t speak French at all and that she could only communicate with me because she put everything I wrote and everything she wanted to say into google translator but she didn’t speak a single word in English.
So we watched a Movie and tried not to be awkward. I wanted to make a move but not being able to speak with her made it very weird for me I don’t exactly know why.
So I didn’t do anything and when the movie ended there was a long uncomfortable silence…
That was probably the most awkward moment in my life.”
37. Good ol’ Joe
Had a friend in college named Joe. He disappeared overseas for a year after we graduated. I stayed here to study and teach. One day, I got a text from a number I didn’t recognize saying “Hey, it’s Joe from business school, want to catch up for a coffee?”
I hadn’t seen him in ages, so I said yes very enthusiastically. I walked into the coffeeshop at the right time, look around for Joe, and there’s Joe from business school. A different Joe from business school. A guy I barely knew.
I couldn’t walk out because he’d already seen me, so we chatted politely for an hour and we’ve never talked since.
38. No kiss for this one
While I was rebounding from a 5-year relationship, I went on a sort-of date with this weird dude from my community college who kinda stalked me, but was pretty much harmless. We went to a wing joint, and he ordered two dozen wings with tons of crazy sauce.
Picture the spiciest thing you’ve ever eaten, and multiply that by 1,000. I sat and stared in horror as he began eating. He had tears, snot, and sweat rolling down his face and dripping onto the table. But (I guess) in some attempt to impress me, he finished every single wing.
He immediately excused himself to the bathroom and vomited everything up. He came back out crying, and took me home. He did pay for dinner though, which was nice. Once we got to my house, he tried to kiss me. Noooooope.
39. VHS and Chill
It was 2001, so I was VHS & chilling at this girl’s dorm room.
It was my first time over there, and there was this giant bear on the bed. Like a ‘got the softball in the milk jug at the carnival first try’ bear. It occupied 50% of the surface area of her bed.
I say, “Whoa, how’d you score that bear?”
Her: “I don’t know…”
Her: “I don’t know.”
Me: “You don’t know?”
Me: “Okay, look…”
Me: “It’s okay if it’s from an ex. I don’t care if you nabbed it. I’ll believe almost anything you tell me at this point. But there is no way you’re going to tell me you don’t know where that giant bear is from.”
Her: “But I don’t know how I got it. Are you going to be able to let this go?”
Me: (looks at bear, bear stares back, eyes full of secrets) “I don’t think I can.”
I got out of there and never looked back.
40. Waste of time
This cute girl from class randomly walked into my dorm room. The door was normally open during the day.
She was in the building visiting a friend and saw me playing guitar so she came in and started flirting. She asked me to meet her at a nearby bar that night at 10 so I agreed. I get there at 10 and she introduces me to her boyfriend. I finished my brew and made my escape.
No idea what that was about.
Glad I didn’t stick around to find out.
41. Online dating is fun
Met a girl online, decided that we should meet for a date. (I’m female BTW – this sort of matters). I arrived in her strange hometown. I didn’t know my way around, so I relied on her to show me around. She took me to a youth LGBT group. I didn’t mind – it’s a bit odd, but I was newly “out.”
Turns out it was just a chance for this girl to show off that she did, in fact, have a date (they didn’t believe her apparently) and that I existed. It was really awkward. When the youth group leader came in, she stood up, grabbed my hand and said “later idiots” and we walked out.
We went to a bar for a drink, and then on for some food. It wasn’t going well. She was very full of herself, but I was new to all this, and in a town I didn’t know.
Once we’d eaten she said, “oh I just need to see a mate who’s staying at a hotel” – fine. Only it turns out there was no friend. She’d booked a hotel room for us for the night! Yeah – I left pretty quickly after that. I may have been inexperienced, but I wasn’t about to be tricked into a night in a rough hotel with someone I didn’t like.
I was a waitress and I had a table of two guys. One was very cute and flirting with me and we exchanged numbers. He asked me out and I said yes. I didn’t really go out much and he didn’t tell me where we were going or what we were doing. Me being young and dumb at the time thought that would be exciting.
So he drives me a pretty good way from my house and we go to an elementary school. I was really confused. Apparently he was a basketball coach and they had a game that night.
At this point I noticed I had no reception on my phone and I really wanted to leave. But I thought maybe we were going somewhere fun afterward so I gave up trying to call someone to rescue me. I sat and watched this game right next to this dude’s mom. Yeah this was going well.
Finally the game ended. We went to get in the car and his friend from the restaurant gets in the front seat making me sit in the back. I am super uncomfortable with this and I ask what’s going on. They tell me they want to “share” me. Nope. Take me home now.
I got lucky. They moped and took me home. I was terrified. That was horrible.
43. Mobbed up
We had just moved to a new area, and we wanted to check out the local shops and restaurants. While we were wandering, we stumbled into a tiny Italian place. Back home, the small hole-in-the-wall restaurants always have the best food, so we were excited to give it a shot. Big curtains were covering the entry windows, so we had no idea what was inside until we trudged through the door.
Inside, we were met with emptiness and silence. We both immediately thought the store was closed, and I spun around and searched for the store hours posted somewhere on the door. While I was looking, we heard a heavy thud.
A woman’s voice barked “I’ll be right with you!”
She appeared, greeted us, and asked “what she could do for us.” Which, looking back, was probably a red flag. But we were naive and hungry, so we said we were there for dinner. She looked puzzled, but motioned us to follow her to a booth right by the entrance.
She then disappeared into the back, and we heard a muffled conversation between our hostess and a man. I asked my date if she wanted to split, but she insisted we stay until we figured out what exactly was going on.
Suddenly, a square-shaped balding man burst through the kitchen door with two glasses of water for us. In a very deep voice he explained that it was his birthday, and we would eat what he felt like making us. We whole-heartedly agreed.
We waited around thirty minutes, and he again returned with three large bowls of spaghetti and meat sauce. He placed two bowls in front of us, and one next to me for himself. He sat with us and ate. We made light and awkward conversation with him throughout, and he kept asking us jokingly if we were the fuzz or with the health board. He was incredibly nervous about us, so my date kept cracking corny jokes because the man would forcibly laugh at anything he took for humor.
He decided we were good people, and didn’t change us for the meal. We wished him a happy birthday, he hugged us, and we went on our way. Easily the best spaghetti I’ve ever had in my life. The restaurant, unfortunately, no longer exists. Also… it was definitely a mob front.
Got set up on a date with this pretty awkward guy.
He picked me up in his car (which was sort of cool considering we were in high school). But oh my god he was a nervous driver. So nervous in fact that he accidentally ran a red light, lost his mind and ducked into a residential area to sit at the end of a cul-de-sac freaking out, thinking the fuzz were coming.
I tried to explain that if a cop had seen him we’d have already have been pulled over, but this dude was too panicked to listen. I don’t remember anything else about the date, just that.
It was uneventful and I never really talked to him again because we had nothing in common.
45. Tinder time
We met on Tinder, hadn’t talked for too long but I thought what the heck? I need to get out more. The first thing he said was, “Oh wow, you’re so pretty!”
Two drinks in, we’re having an awkward conversation, and he’s buying me double G&Ts instead of the singles I’m asking for. Mid-sentence, he grabs my face and says, “Sorry – I just need to get this out of the way.”
Then he forcefully sticks his tongue down my throat. I didn’t really know what to do because I didn’t want to cause a scene.
I said I needed to look up the time for the last train. He said, “no it’s fine you can stay at my place!” He begs, saying he’ll sleep on the couch, he just wants to get to know me better. I said no. He huffs, very briefly, and then cheers up and tells me he’ll look up the train time for me “like a gentleman.”
He says it’s at 1 AM. I said that’s late, is he sure? He gets all tense and says, “What? Don’t you believe me!?” I smiled and said, “of course not.” I excused myself to the toilet and checked the times on my phone. (The last train was actually at 12: 15. Lovely.)
I went back to my seat, told him I’m getting an uber, goodbye. He tried to beg me to stay, loudly and embarrassingly, so others could hear (hoping I’d get so embarrassed I’d go home with him I guess?) and even pretended it was his birthday and yelled to the bar that he was protecting me by taking me home because “taxi drivers can be rapists.”
I told him that I was going home; he loudly asked for a hug and tried to grab my bewbs.
46. A great guy
This guy I met online was half an hour late for the date. The first thing he said to me was: “You’re too tall. You’re taller than me.” I’m 5’5, and I was wearing flats – nowhere on his profile was his height listed, never mentioned anything about it. He said he’d buy me a drink for being late, so I figured I’d get a brew out of it.
We chatted for a bit about our jobs and school and whatever. I check the time, and realize I have to catch my bus back home – I lived in the suburbs with my parents at this point. He says “Okay, I’m coming with you.”
“Well, I guess you can come back to my place. My roommate is there though.”
“I’m not coming home with you.”
“I bought you a drink! You owe me! …Whatever. You’re not even that hot.”
“I am not going to sleep with you. I’m going home.”
He just stalks off in the opposite direction. Then, amazingly, I get a message from him later.
“Look, I’m sorry. You’re a great girl and I enjoyed our time together. But this just isn’t going to work out.”
Um, yeah. I thought that was obvious.
I came across this dude on another dating site later. His profile was a picture of his abs; his secondary pic was him ‘s*xting’ with a girl. “So you know I can satisfy the ladies.”
Good luck with that pal.
47. An OK Cupid entry
I met a guy from OKCupid.
The first time we met up in a public place and just had a casual chat. It wasn’t a horrible date, but it wasn’t very memorable either. I decided to give him another try because it could have just been nerves.
The second date he invited me over to his place… I knew he lived with his parents, but I kind of assumed they’d be away.
They were still there.
They kept coming into the living room and giving us iced tea and chips while he played XBox in his track pants (no shirt) and I sat there awkwardly watching.
He didn’t really speak much to me.
By the way, we were both in our 30s.
I went to the movies to watch Inception with a girl I met online.
Once we got there we started walking inside and I realized I didn’t have my phone in my pocket. I said I must have left it in the car and started to walk back to get it. She was trying to get me to leave it and saying we would miss the film but the phone was only about a week old so I was really paranoid about it. We checked the car for about 10 minutes but we couldn’t find it.
A couple were parked next to us so I asked them to ring my number because I couldn’t find it.
It started to ring and it was obviously coming from my date’s handbag.
She threw the phone back and literally ran away.
Yeah, we’re still cringing from reading all of those. Yikes!
Now it’s your turn! Have any stories you think would really turn people’s heads?
Share yours in the comments!