With that guy who used our “date” as an opportunity to run errands. I clearly remember a few minutes at a CoinStar machine with him.
Worst dates? How about bizarre ones? I’ll omit my actual worst dates because I suspect they’d be too intense or bring down the mood, and I’m guessing that may not be the intention of the post.
I briefly dated this one girl in Portland, Oregon. Let’s call her Marie. I planned everything for the first date, drove all the way across town for the sake of meeting at a memorable place on a pleasant day - effort I put in when I think there’s a chance for something with real potential.
We met up at a farmer’s market, awkwardly scooted around looking at various produce and tasted spicy chocolates while talking about who knows what. Positive, light-hearted conversation. Cool, Marie passed the vibe check, so I took her to my favorite bakery in the area. Better conversation this time - enough to want a second date. We started walking maybe two blocks until she excused herself and dipped out - no hug, kiss, or handshake. Huh. Well, it was less than a 90-minute date. OK, bye bye.
A few days passed as we kept in touch over text and agreed to another date. I, again, made all the plans; I don’t remember what they were exactly but do recall that it was a very thoughtful and cute idea based on some cute thing that we bonded over when we were last together. Marie said no, she’d actually prefer to go to a book signing at Powell’s (which is downtown, across the city for me) in the middle of the week at, like, 5pm. Hmm, OK, I’ll give it a shot. I appreciated her proposing a date idea and hadn’t been to a book signing in a long time, anyway.
The day came. I scrambled after my last meeting for the day to shower and prep and whatnot, hopped in my car and enjoyed a ~45 minute drive in heavy traffic toward the heart of the city. I eventually found paid parking about 4 blocks away, tossed a few coins to my Parking Kitty, and rushed off to the bookstore.
I composed myself while looking around but saw no sign of Marie. 5 minutes until the signing, whew. I texted her to say I’d arrived. I started to meander, peeking around the stacks to see if she’s browsing but stayed to the entryway. It’s cold and drizzly outside, enough where people weren’t loitering around, so I didn’t think we’d miss each other that way. 0 minutes until the signing. 5 minutes late. I texted again. 10 minutes late. Then there she is - there’s Marie! A brief “hey!” later, we scurried upstairs and, thankfully, saw that the group was seated but the crowd was still murmuring, so the event hadn’t yet begun.
We grabbed our seats and enjoyed the event, after which I anticipated that we’d walk and talk around the bookstore or do… something date-y, but she said “OK I’m gonna head out.” Uh. “Alright, can I walk you to your car?” She nodded, and off we went. We made it about two blocks and only chatted for maybe 2-3 minutes before reaching her car. “OK, bye!” she said as she got in her car with a timid wave.
After I got back home, I texted Marie, asking if she was OK because it felt like we only shared a few sentences before departing and I’m not used to that kind of communication, especially on dates. No response. I waited two days, still no response, so I told her that it was nice seeing her but I need better communication with people I’m dating.
I used to use this as an icebreaker, until I got a very uncomfortable response from a female colleague. Turns out that whilst men’s “worst dates” are usually weird or awkward, and tend to make for good light entertainment and a little window into their lives, women’s are way more likely to be sexual assault related… Made me wonder how many answers I had heard in the past were glossing over some trauma that didn’t need to be brought up in a social setting.
I now usually rely on the way more positive “what’s the next thing you’re looking forward to?”.
Holy shit, same. My worst dates were funny in hindsight, awkward or just didn’t work out for me. I heard some interesting and weird stories too, but a lot of them were: “…and then he grabbed my arm and said: i’m coming with you”
I was in college. During a volleyball game at an away school, one of the girls on the other team came up to me to ask about my serve. (I did this weird side-arm thing rather than overhead.) She was cute and nice, so I asked her if she would like to exchange info. We talked more, and I eventually asked her out. I brought her to a nice place for dinner. She ordered a steak, then proceeded to pick the whole thing up with her bare hands and raw dog the steak. I was instantly turned off. I told her I wasn’t feeling well and ran to the bathroom. I found the waiter and paid for everything, then I went back to the table, told her I was sick and needed to go home, but I paid for everything so please enjoy the meal. She called the next day and wanted to meet up again. I told her I’d hang, but only as a friend and I didn’t want to take things further. She threatened to kill herself, so I called emergency services, and let them handle that. Still the biggest bullet I ever dodged.
Tinder date, my train was late so late so we meet at the train station and walked to the bar. On the way I had a smoke and he told me in lengths how he quit smoking a while ago and how good it was. That’s when I realized he talks with a fake deep voice, sounded like he’s trying to imitate Batman…
At the bar he switched between small talk and his seemingly hot roommate, he’s definitely not interested in, otherwise they would have had sex already (obviously!).On the way back to the train station he wanted a cigarette from me.
Nothing bad, just weird flexes all over. The voice killed me…
I remember a story where op saw a video of her bf years ago and realized he was gradually making his voice deeper over the years to sound like batman today. Like some wierd long con. Wish I could remember the rest.
There’s a story I heard on smash reads Reddit about a woman whose bf was faking a deep gravelly voice for the two years they were together. She said his real voice sounded like a joke muppet voice…so she laughed when she first heard it, reconfirming his worst insecurities about his voice. Rough.
I was stuck in a shitty backpackers on top of a ski mountain with 3 random Russian dudes, swiping on tinder, when a man named Moses gave my a bag of shrooms for free. Moments after I ate them, a woman matched me on tinder and wanted ed to meet up. So I walked further up the mountain to a fancy lodge where this tinder date, I shit you not, introduced me to her family, who were clearly millionaires. There was a gala that I was absolutely not dressed for, and I spent about 30 minutes talking, eating canapes, and tripping motherfucking balls before realising I was too high and getting higher, so I just fucking bounced, went back to the hostel and did about a week’s worth of shits in 1 hour to the dismay of my angry soviet roommates.
Not a word of this story is made up.
They invited me to a pool party. When I got there they were baptizing people in the pool. Yeah, stayed for the hot dogs though.
…you aren’t funny…
lmao smash that downvote button then. No need to reply.
Back in college, a female friend hooked me up on a blind date with her friend. Hands down she was the cutest girl I’d been on a date with at that point in my life.
After some back and forth it ends up being a double date, which was no big deal. But it was with a random engaged couple I didn’t know. Which was fine. But they picked Macarroni Grill or Cheesecake Factory or similar restraunt on a Friday evening. It was like an hour and a half wait. The couple wanted to wait, there was a mall nearby, so the other couple went off by themselves shopping and left us alone.
So, for the next hour or so I tried my hardest to engage in conversation with this girl. I’ve lost count of how many first dates I’ve been on. My small talk/get to know you banter is solid. But it was no match for her lack of social skills and one word answers.
I tried everything and ran dry WELL before the couple finished shopping and we actually started the meal. We sat on a bench and I’d break the awkward silence with the occational: “So, see any good tv/movies lately?” Only to get a “Not really” back. Or “What sort of hobbies do you have?” “None really”.
She didn’t come off as disinterested or bored. It felt like she wanted to be there, but if we were a ven diagram the only overlap would have been our mutual friend.
It was the most painful 3 hr date of my life.
Oh that does remind me of an experience. I can normally make people laugh when I crank up the charm but o boy this person was not having it. Just hated to be alive and wanted to run away to a third world country to teach yoga or something. Normally you would pass on a second date but for a 10/10 hotness scale I had to know if it was a bad day or something. So we met up one more time at a comedy club. Dead face whole time not a single laugh. Meanwhile abs hurt from all the laughing. Then got a we dont have chemistry text later 🤣.
Dude I had a very similar experience. I got literally nothing from her for 2 hours, and then when the date was over I just left and said well goodbye.
Later got a series of messages from her friend asking me why I was so rude and disinterested.
It’s like bitch, I must have spoken 200,000 words that date, and the chick spoke 200.
Like what am I supposed to do, just talk in your ear for the whole relationship or like what’s going to happen here… fuck this.
Oh absolutely. I spoke with the mutual friend after and she was being all coy asking me if I was going to ask the girl out on a second date. Hard Pass.
She looked a little sad, I think the date girl had a nice time and was willing to go out again, but I explained my perspective from the date, and the mutual friend reluctantly understood.
Mutual friend never explained why the date girl acted like that. If it was just shy nerves, I probably would have given her another chance, but that’s probably just how she is.
princess entitlement. she’s mad you didn’t salivate all over her for just existing. probably said you were ‘low effort’ for not taking her to a more expensive place too.
strong incel vibes
I just told her friend that I could have taken a mannequin on a date and it would have been just as interactive.
Of course, that was like pouring water on a fish for all the effect it registered.
I’ve met people like this. They literally… do nothing. They seem to aspire to be empty inside and outside.
And they think people who have interest/hobbies/friends are ‘weird’.
Same. I cant stand boring people! Like you think theyd be depressed at how boring they are
I mean, it very likely is depression.
Im more talking about the people who are content doing nothing but watching tv all day, they appear happy, but dont really do anything.
Thats probably just how normal people are though. I feel like the day is wasted if thats all I do (unless im just relaxing from work, thats a little different. But at some point I cant relax any more)
Nothing fancy. Date one after a couple weeks of talking. I made it clear I wasn’t down for physical shenanigans yet. After a drink he got a tiny bit handsy. Second drink, he moved to my side of the table and tried to get very handsy. I paid my half, said I was ready to leave without becoming confrontational. He clearly thought my boundaries had changed with a couple of weak drinks. On the walk to the car, he continuously tried to bully me into kissing him (absolutely not) and then tried to shove me in his car after pressuring me into a hug goodbye. I bit him on the titty and drove home like a maniac.
Had actually been dating this girl for about a month. It was 4th or 5th date and she wanted to go play pool. Which was fine with me as at the time I loved to play pool and had my own cue. So I took her to one of my favorite pool places where we could rent a table by the hour.
We had been there about an hour and stopped to get some food. The place had a bar with food and TV’s all over the place.
We sat down and started eating and talking. Nothing serious, just chatting between bites.
Then she drops this: “You’re one of the weirdest guys I’ve ever met.”
Somewhat shocked I asked why… Her response was that I wasn’t watching the football game playing on all the TV’s.
I took a moment and looked around and sure enough most, if not all the guys in the room were glued to the TV… I looked at the game playing, saw a football game, shrugged and stated that I’ve never been much of a sports fan.
That ended the relationship. We talked a couple more times after that, but we never went on another date. She called me about a month later complaining that some guy she met in a bar won’t return her phone calls. That was the last time I ever spoke to her.
I still don’t watch football, baseball, soccer or basketball. I’m a skydiver, why would I care about some game that only requires one ball?
this feels like she was mad at you for not being able to complain about you ignoring her and watching the game.
you paid attention to her and treated her right and she didn’t like that. I’ve been there before.
I’ll just say it… She was nuts. The sex was OK, but not good enough to deal with crazy. Fortunately, she was not the smartest and the games she attempted to play were all things I had seen before and she had the subtly of a brick. So it was pretty easy to avoid her traps. That probably lead to what happened that night. I wasn’t fulfilling her supply needs and wanted to find an easier target. At least it has made for a good story 22 years later.
Also, It all worked out in the end. About 6 months after the above happened I met the future Mrs. CanopyFlyer. We’ve been married 20 years now and have two kids.
Just for kicks, after posting above I looked up Pool girl on Facebook, she has a fairly unique name. She lives in Boston now, the event above took place in Cincinnati and she is apparently still single 22 years later. At least her profile does not show anyone but her. She is 4 years younger than me so that puts her at 51 single and no family.
I get people not wanting kids. I didn’t until I met Mrs. Canopyflyer so no shade on Pool girl on that, but I cannot imagine still being alone at my age. With that said, I do have a friend that is my age that lost her husband to a heart attack this year. That’s been pretty devastating and I feel so badly for her.
Hockey has zero balls, 24 sharp pieces of metal moving around at 20-25mph, and a hard chunk of rubber moving at speeds of up to 100mph.
But I get your point.
I have two kids.
Oldest is a figure/ synchronized figure skater
Youngest is a hockey player.
Believe me, hockey is a LOT more civilized than figure skating and especially Synchro.
Even before you were talking about football and baseball I could tell you were US American by going on 5 (five!!) dates before having kissed or fucked lol
Long time ago. Went on this date from a dating website. She seemed cool online. We talked about cooking, hiking, and gaming.
Within minutes of meeting up she got put out a really weird vibe. She tried to change our plans from meeting at a bar for a drink to some expensive dinner place. I said no, lets just get to know each other first. She got angry, but stayed. Kept telling me how weird I was but she thought I was cute anyway. OK. We ended up going to another bar after like 20m, that was basically the same as the one we were in but she thought it was nicer or something. OK.
After sitting down at the second bar, and ordering a drink, she gets serious and stares me in the eye real hard and goes 'What is wrong with you? Why aren’t you in love with me yet? I’m trying so hard and you must be messed up in the head to not be totally in love with me by now. Every guy I meet loves me within minutes of meeting me." I just laughed my ass off at this absurd outburst. She got so angry, like gripped the table and starting ranting on and on about how men suck, how stupid I am, how amazing and hot she is, how pissed off she was because I should be eating out of her hand.
Anyway, I let her rant for awhile, maybe half an hour? She basically started talking to herself and like trying to convince me to bone her, and also going on about how she was some yoga teacher and had mental superpowers or something totally ridiculous. I finished my drink and dropped cash on the table and told her what a wonderful time I had, and I’d never like to see her again. She was completely mind-fucked by that and went totally silent. In her delusion land apparently no guy could ever not want her.
She sent me a bunch of really weird texts later and I ignored them. I’ve never met such a totally delusional weirdo before or since. Ever since that date I refuse to date anyone to references Burning Man as something they like doing.
Went to the biggest theater in the country, fancy place, fancy people. Girl tried to open a puffy bag of popcorn by smashing it between her hands (like you’d do in a barf bag prank). Loud bang. Popcorn everywhere.
I didn’t really hold it against her, but she felt so bad about the embarrassment she hated the sight of me forever from them on (we had common friends so we kept meeting many years after).
Drove a significant distance to pick her up.
Our planned outing date turned into “come hang out at my place”
Come hang out at my place turned into “oh I’m actually at my mom’s house RN but she’s on vacation and I’m just house sitting”
“I’m just house sitting” turned into “I’m 26 not the 38 I stated in my profile, and my mom is here but don’t worry”
That turned into mom sending her text messages asking what the fuck this weird old guy is doing in her house.
That turned into me leaving under a cloud of complete embarrassment.
What a fucking dumb cunt.
I’m 26 not the 38 I stated in my profile
What a weird age to lie about!
Maybe she likes older guys but not the kind that are looking for younger women.
I would normally say that at least she’s after guys that aren’t creepy by default, but I feel that more applies to guys chasing ladies under 21, not someone who’s in their mid-late 20’s
Yeah you actually nailed it. It’s a very similar process of women who are fat, but they do not want fat fetish guys, they just want guys who will accept or like them without that underlying, highly specific lust.
The truth is I have sex with a lot of younger women. But not that level of age gap. And lots of younger women love older dudes for many reasons. Most are just able to say it out loud without playing all these crazy games.
I think what happened was she was expecting mom to go out with her cousin or something for a movie, and she could get a quick bang but mommy stayed home unexpectedly, and she thought she could still get the bone and nobody would be the wiser.
That’s the kind of clueless, selfish thinking a ~25 year old woman does. Which is why I date 30+ usually. Women (men included) are still idiots until the brain development stops. I kinda clued in that I was lied to about the age when I got there, but you can never really be sure. I mean, I look at least 10 years younger than my age/cohort.
at least it wasn’t her cop dad that was home?
Gal was a friend of a friend. Met her in passing at a show one time and said we should go out. She invited me to come over hers and we’d go see her “friend’s band play” at a nearby bar. Got ready with her and her roommate. Was around Halloween so I intended to splatter a bunch of fake blood and paint on myself for a zombie - her and her roommate helped and she helped herself to apply up under my torn up shirt so I was thinking “wow this is going swimmingly already”.
We go to the bar she seems to know everybody and keeps handing me free liquor. Watch a couple bands, talk to a bunch of her friends, and I’m honestly having a great time also getting pretty drunk. She introduces me to this one dude and the vibe is weird like he’s being subtly hostile. Turns out this dude was the “friend” in the band.
Anyway night goes on late she’s hanging onto me off and on, pretty handsy. We decide ok time to head back to her apartment - I’m not really expecting anything but she’s been sending pretty big signals all night and I’m happy to get back to hers. As we’re leaving her “friend” in the band calls after her. She tells me “oh hold on” and goes to talk with the dude. Conversation seems involved. I kind of just hang around a bit awkwardly just listening to the lingering conversations around me unsure how long this is gonna take. Eventually 20-30 minutes go by and I’m looking around and they’re nowhere to be found.
I’m pretty drunk and about 3 miles from this girl’s apartment - I decide fuck it I’ll walk back. I had left some things in her apt so I needed to get them.
Get to the apt after a long walk and knock. It takes a couple minutes for someone to answer - gal in question answers the door disheveled and scantily clad and says oh hey I’m sorry uh I kinda lost you. I’m kind of mad at this point and just say “yeah I just wanna get my stuff and use your bathroom if that’s alright.” She stares at me a second real awkward and says “uhhhh yeahh I don’t think that’s a good idea” and it clicks for me.
I burst out laughing my ass off in the middle of the night on this empty street. I tell her “dude just bring me my things please”. She doesn’t say anything else but goes up and brings my stuff down. I wait 30 seconds, piss on her front porch, and go to sleep in my car. Drive home hung over next morning.
Tldr: she ended up banging her “friend” in the band we went to go see.
I had talked to that girl in a karaoke bar once and we swapped numbers. Had forgotten about her but half a year later she texted me if I was in for a date the same evening. Should have been a red flag already since this is weird, but I was curious… and horny. Date: after 10 minutes of small talk and funny banter she told me that her boyfriend is at home and does not know she’s on a date. No idea why she told me. Was she waiting for some approval? Anyway I was flabbergasted but didn’t decide to call it off right away (I should have but again, I was curious … and horny, even though a little less so now). First hesitated and a few bars and drinks later I decided it’s her responsability not mine and we had some fun later that night and never came back to it until a few weeks later she texted me a whole ‘novel’ full of reproaches, as if I we had had a long relationship and I had broken up on her or so. Absolute weirdo. Friendly reminder to always always ALWAYS wear a condom (I did).









