What's The Worse Or Funniest Date You Ever Been

[Solomon]

I've been on a few awkward first dates that at the time was like WTF but now I can laugh at, these 2 stories are from this year alone.

Story 1 Early January

I met the girl on Bumble this was January, short chick but with a nice ass in her late 30s. We went to a bar to have some drinks. Then she started getting into the story of why she and her husband divorced. Come to find out he was a closeted "Crossdresser" who wanted to come out to his wife. She started getting into details of him liking to get pegged etc and seeing her husband order dresses on Amazon. In between sips of her Long Island. Mind you while she is telling the story her voice is loud as ****. I'm trying to redirect the conversation but nope now it's trauma bonding time for her or therapy and keeps going. I'm trying to tell her to keep it down cause the bar is packed and even though we are in a booth, I know people can hear us. She of course says she doesn't care and doubles down on her voice, going louder at this point I know this girl is off, and I'm making exit plans.I try to finish the date as quickly as possible. Ended up walking to her car and she is sobbing about the state of her life then asked me to go home with her(if you catch my drift), I was so turned off that I declined and never saw her again.

Story 2

This happened a few days ago. I was talking to this girl (on Bumble) She seemed like the nature type, you know, likes to go camping, hiking being in the woods. She was tall 6'1, volleyball player built chick, nice small tight ass. From talking to her I thought she was going to be one of those book worm types, Boy was I wrong! I met her at this dive bar I like to go to. She show's up in a hoodie and sweatpants. hair is not done, not even make up it's like she got up from hours of her couch and straight to the date. I mean it was appropriate for the venue but I was put off, for a first date even sweatpants are low standards in the Midwest. I know I'm not feeling her of the bat. So I'm counting the minutes before I leave. Ended up finding out she was an alcoholic. She is bragging about how much she drinks and is proud to be a self-proclaimed alcoholic. She asked me If I like cigars. I say I do. She says she has cigars from her recent trip to the Dominican Republic. We go in her car to smoke a Dominican cigar. As soon as I enter her car smells like diaper ****, it was disgusting. After 2 puffs from the cigar I couldn't sit there anymore and told her I had to work early. Deleted her number when I got home.

Share your stories

 

[crowolf]

When I was around 14 years old, I met a girl online on an app called MeowChat (not really a dating app but sort of like a social media thing).

She was from my city but then I had to go and live abroad. So we texted for a year and a half. We were like best friends. There was some flirting here and there but for the most part It wasn't a male-female dynamic (totally expected for a teenager).

After all this time of daily texting, I got back in my town and we set up a date. Guess what happened on the date. We barely talked, because we have already discussed everything over text. We had nothing to talk to. Or we were both shy. Maybe the two factors combined.

Things got better eventually, as we decided to continue "dating". But this was my lesson to never text too much before actually going out.

 

[The Duke]

Ohh boy where do I start.

So I met this $tripper....all I did was walk up to the main stage flirt a little, and tell her she had good taste in the music she picked and she should come see me after she got done. 20min later she is at my table and we hit it off. It was my buddy and I and her at our table drinking and having a good time. She was about to be off her shift so I asked her if she wanted to hit a couple bars with us and she agreed.

We show up at a fancy luxury hotel bar that has a pool and bar set up that all the high-brow people go to. Her and I end up knocking an entire table into the pool. Not sure how that happened but we thought it was hilarious as we watched the table sink to the bottom. After the sinking of the titanic, we decided it was time to go before we were asked to leave.

Minutes later, we are headed up the freeway in my buddy's junky 20yo mini-van with the windows down because of no a/c. He is driving and her and I are on the middle seat. She was bent over, panties dropped, while I fingered her while her long hair blew every where.

Turns out this chic lived in a half-way house(drug conviction). She wasn't supposed to be stripping per agreement to live in the house but she said she pretty much sucked at everything else and stripping paid really good. lol.

That girl was tons of fun to party with. There was never any drama with her, she always kept it real.

She looked like the girl in this video and this was one of her favorite songs. We nicknamed her Tawny Kitaen in reference to the video model. God bless her wild soul.

 

[BeExcellent]

My husband has told me this story about a girl he met in an internet chat room years ago (when those were a thing). He chatted with a chick who lived 4 hours away. He must have been smooth without exchanging photos because after about an hour of chat this girl offered to drive to his place. He didn't believe her but dared her to drive over, and gave the address.

Well she showed up 4 hours later, in the middle of the night. Brought her dog, an Alaskan malamute with her. She was as advertised (again no photos before hand - this was before cell phone cameras), and so was he. So needless to say nobody got any sleep that night.....and he never saw her or heard a word from her again. Forgot her name. She left with her dog while he slept. That experience had him sprung for several months. They never exchanged numbers, lol.

I've had a few awful first dates. Nothing particularly spectacular to report.

I did have a sexy man ask me for my number on the NYC subway once. Ended up dating him for a year. He asked for my number in the 2 stops on his way from his office to his raquet club one evening (about a 6 minute time span total), and 5 minutes later called to be sure it wasn't a bogus number. Took me out the next night. Very sophisticated hot dentist, turned out. Bold & unapologetic, just a great guy. He never was going to marry or have kids (why we split), and still is in NYC with a 10 year live-in gf who is a bond trader. Lots of fun adventures with that one.

 

[justaroundthecorner]

Worst case scenario - one woman I stopped dating (we had fiery argument) matched me again with false profile on Tinder, then played me (tricked me) to set up a date with her false identity and I went to first date with no one (I was planning to love bomb chick so I had flowers with me - roses went to garbage). She tried to do it one more time after that but I knew what to do this time. She gave up picking on me online after that (I was sad we stopped seeing each other at that time, she was hot and had a lot of female allure).

Funniest dates I had - it was always in ZOO - animals are really cool, interaction with them in ZOO gives a lot of options to discuss humans, mating, emotions, there's a lot of making fun about animals or being like them. I seriously think ZOO is awesome for the second or third date.

 

[The Duke]

#1
One girl I met for a first date at a restaurant, and we hit it off well so I asked her if she wanted to go to a sporting event after we were done eating. She was down for it but she was very over dressed. She had some extra clothes with her so we stopped by her car to get them. I figured she would just change clothes in the bathroom at the event.

Uhm nope, we are driving down the road and she starts undressing in the front seat of my truck! I'm thinking this date is going better than I thought.

#2
I was on a second date and met my date at a country dance bar. I always got in free and whomever I was with did too because I knew the bar tender. The bar tender happened to be really hot, and always remembered my drink order. I always made sure to get my drinks from her and say hi whenever I showed up. I introduce my date to her and everything seems to be good. She tells my date how I'm a great guy and tries to make me look good.

A few minutes later I ask my date if she wants to dance and she says yes, but she has to go to the bathroom first. I'm waiting for her and after about 15minutes I decided she isn't coming back. I call/text her phone and of course she doesn't answer. Its obvious this wh0re took off.

I suspect she got insecure because she thought I was banging the bar tender, or there was some other guy in the picture.

It was definitely a blow to my ego. A few days later I called her up and she had blocked my number.

 

[BaronOfHair]

Had more than a few that were less than satisfactory or hilarious, nonetheless my worst and most hilarious(to date)are one in the same:

Visiting Bucharest in my late teens, when I was still mistaking Chris Hitchens for a deep thinker, and convinced that our species had it all figured out. Picked up some chick outside the city limits shortly after sunset only to discover, as we were making out on the back seat of the Vespa I'd rented, that legends and mythology https://en.m.wikipedia.org/wiki/Strigoi are often built on a grain of truth

I was still a smoker at the time, and that Zippo fluid in my pocket was put to unusual(by Western standards)yet life-saving use. Explaining to the locals why something that still kinda sorta seemed human was running down the road, decked out head to toe in conflagration, when my command of Romanian was all but non-existent... In hindsight, THAT was pretty f-cking hilarious