Tell Me Your Worst Dating Story?

[BigOrangeMojo]

I had this date scheduled with a girl that I really liked. Went over to her place to pick her up. Her roommate answered the door and my date was back in her room with her ex bf "enjoying themselves." I decided to leave.

A few mins later, a friend of mine called and was like "We're going to corn maze and haunted house and then to Platinun Plus (strip club). I ended up going. In the line at the corn maze, we ran into some girls (My friend knew one of the girls). They were all dressed up for the maze in costumes. One of the girls had full zombie makeup on face. One of my friends asked the girls, wanna go to Platinum with us and we went to Platinum. The girl with the zombie makeup was like "I dont really wanna go in." I told them to go in and that I could take her back to her apt. I was such a gentleman (that and her costume was pretty form fitting). That girl was like wanna go to D&D (a country western bar) and I was like sure. We got in D&D and there was a mechanical bull. She was like I bet I can stay on longer than you. She told me to go first and I actually did pretty well. She got on the bull. I will keep this as PG as possible but she REALLY enjoyed the mechanical bull ride.

Me and her seemed to be getting along really well. We ended up picking up everyone from Platinum and getting their drunk selves back home. I dropped her off at her place, went in for a kiss and she stopped me and was like "I got in a big fight with guy I'm dating a couple of nights ago and we havent spoke since. I can't kiss until I officially tell him we're through."

Yeah, wasn't my night. I had less game than the mechanical bull.

 

[Regulator]

I had this date scheduled with a girl that I really liked. Went over to her place to pick her up. Her roommate answered the door and my date was back in her room with her ex bf "enjoying themselves." I decided to leave.

A few mins later, a friend of mine called and was like "We're going to corn maze and haunted house and then to Platinun Plus (strip club). I ended up going. In the line at the corn maze, we ran into some girls (My friend knew one of the girls). They were all dressed up for the maze in costumes. One of the girls had full zombie makeup on face. One of my friends asked the girls, wanna go to Platinum with us and we went to Platinum. The girl with the zombie makeup was like "I dont really wanna go in." I told them to go in and that I could take her back to her apt. I was such a gentleman (that and her costume was pretty form fitting). That girl was like wanna go to D&D (a country western bar) and I was like sure. We got in D&D and there was a mechanical bull. She was like I bet I can stay on longer than you. She told me to go first and I actually did pretty well. She got on the bull. I will keep this as PG as possible but she REALLY enjoyed the mechanical bull ride.

Me and her seemed to be getting along really well. We ended up picking up everyone from Platinum and getting their drunk selves back home. I dropped her off at her place, went in for a kiss and she stopped me and was like "I got in a big fight with guy I'm dating a couple of nights ago and we havent spoke since. I can't kiss until I officially tell him we're through."

Yeah, wasn't my night. I had less game than the mechanical bull.

You were like

 

[Firebirdparts]

That is an atrocious story indeed.

 

[MAD]

Don't mess around with married women. In this particular scenario, this woman was "leaving" her scumbag POS husband because he was verbally/physically abusive to her AND had numerous affairs on her. We go out to dinner, have a couple drinks, laughter, flirting, conversation.... really just an awesome first date. She stayed at my place that night because she was too tipsy to drive home, but we didn't do anything more than make out. Spent the next day together, just hanging out (actually rode over to the Jeep Invasion in Pigeon Forge) and she was already getting a little distant towards the end of that day. Of course, the next day, she tells me that she just can't leave her husband, even though he's a POS and treats her terribly. We repeat this scenario over and over several times over the next year and a half or so....every time it winds up the same way. I swear that Cole Swindell wrote "Break Up in the End" about this relationship. After totally distancing myself from her for a couple years, we've become friends again, but that's all. I just don't think I could ever try the relationship thing with her again, even though she did finally leave that POS, got divorced...the whole nine yards, but I'm also now in a relationship and I'm the happiest I've ever been, including my 13+ year marriage.

I can't help but think sometimes about "what might have been" but then when I think about how happy I am now, it just makes me believe even more in fate and how things work out the way they're supposed to.

I was expecting you to have a run in with POS husband, thank goodness that wasn’t the case.
Sounds like you made out in the end, nice story.

 

[MAD]

One more story to tell, but not about the first date, just the relationship that sprang from it. Went out with a lady that I'd matched with on Tinder (first red flag!! lol) even though she only lived in the next town over and we had numerous mutual friends, and we worked in the same profession. First date was ok, nothing remarkable, but we set up another, then another, etc. Fast forward a couple months. It's still nice. We get along great, have some stuff in common, sex is good...but I'm also noticing that we have some basic, philosophical/ideological/political differences that are eventually going to be a problem. I went to NJ to work for 8 weeks during the pandemic, but we keep in touch (phone calls, FaceTime, text, etc.) while I'm gone, and then we pick back up with dating once I get back home. We're still getting along well, but I still know in the back of my mind that we have those differences that are going to be too much to overcome. Plus, I'm just not getting any "closer" to her now after 8 months than I was when we first went out. She's noticed this same feeling and calls me out on it, saying "I just don't feel we're as close as we should be after how long we've been dating." My response?? "You're right...and we're not getting any closer than we are right now." She proceeds to tell me that I can't predict the future, we don't know how we'll feel about things and another couple months, people change, etc. I told her under no uncertain terms "I do not love you. I'm not in love with you. I'm not ever going to be in love with you."

She basically said "Wait. Hold up. I didn't mean what I said about us not being as close as we should be. We're good. Let's work on this!" She basically refused to let me break up with her. I didn't have any other interests at the time, and I wasn't even mad at this one, no real reason to "break up" even though it was never going to last long-term, so we kept on, strictly FWB from my perspective, which I wasn't really proud of, but she was given all of the pertinent information.

I finally ended it for good a month or so later after I couldn't ignore any more of the crazy, conspiracy theory BS any longer and I pretty much had to ghost her because even then she was still begging me not to give up on us. "Hello!?!? There is no 'us'! You were given all of this info a couple months ago...and you didn't want to believe it."

Sounds like she desperately didn’t want to lose you, is she still trying?

 

[MAD]

This isn't the worst, but maybe my weirdest for me. Back in the day, I was in a bit of a rut in terms of dating...I was getting more responsibilities at the office, becoming more active in a young professionals group in town, etc. Anyhow, a good buddy of mine convinced me to give the whole internet dating thing a go.

After a couple of uneventful first dates with a few gals that didn't lead to second dates, the next one was a bit...odd. She lived a couple of towns away, but judging from her profile she was relatively cute, had a stable career (librarian), and seemed generally normal after some messaging back and forth. I scoped out a few restaurants in her town online, found an Italian place that, even if things didn't develop with the gal, at least it'd be a good dinner from a food standpoint. So we set up a night to meet up, the veil of normalcy still in place.

At the eatery, I noticed she was a bit more "Goth" than her profile pics let on...not my thing, but hey...I was hungry for some lasagna at any rate. Maybe the conversation would reveal some common ground, right? We talk books and literature for a bit, and she asks if I'd like to know why she's wearing the all-black getup (apparently my expressions made it more obvious than I had thought). She proceeds to tell me that she's heavily involved in a vampire-themed LARPing group in the area and they're meeting up later that night. Apparently they got together and drank "blood" (koolaid or wine) and did fake vampire stuff around a fire from what I gathered. She did extend an invitation which I politely declined. My dinner enjoyment at that point was in decline as I kept imagining her looking at the marinara on her plate in an unsettling way. There was no second date, haha.

O M G, that is the craziest story. Lol, so funny. This sounds like it could be a SNL skit or something.

 

[MAD]

I had this date scheduled with a girl that I really liked. Went over to her place to pick her up. Her roommate answered the door and my date was back in her room with her ex bf "enjoying themselves." I decided to leave.

A few mins later, a friend of mine called and was like "We're going to corn maze and haunted house and then to Platinun Plus (strip club). I ended up going. In the line at the corn maze, we ran into some girls (My friend knew one of the girls). They were all dressed up for the maze in costumes. One of the girls had full zombie makeup on face. One of my friends asked the girls, wanna go to Platinum with us and we went to Platinum. The girl with the zombie makeup was like "I dont really wanna go in." I told them to go in and that I could take her back to her apt. I was such a gentleman (that and her costume was pretty form fitting). That girl was like wanna go to D&D (a country western bar) and I was like sure. We got in D&D and there was a mechanical bull. She was like I bet I can stay on longer than you. She told me to go first and I actually did pretty well. She got on the bull. I will keep this as PG as possible but she REALLY enjoyed the mechanical bull ride.

Me and her seemed to be getting along really well. We ended up picking up everyone from Platinum and getting their drunk selves back home. I dropped her off at her place, went in for a kiss and she stopped me and was like "I got in a big fight with guy I'm dating a couple of nights ago and we havent spoke since. I can't kiss until I officially tell him we're through."

Yeah, wasn't my night. I had less game than the mechanical bull.

Well told story, was hoping it would have gone in a different direction for you.

 

[MAD]

A wise man once said that some of God's greatest gifts are unanswered prayers.

So true, wasn’t there a song kind of like this?

 

[Regulator]

I was expecting you to have a run in with POS husband, thank goodness that wasn’t the case.
Sounds like you made out in the end, nice story.

He's a sawed-off little POS. Crazy enough to maybe slash some tires (which he did hers on more than one occasion) but not man enough to come after anybody face to face.

 

[GrayWaterCanine]

So true, wasn’t there a song kind of like this?

Chris Gaines I think.

 

[Regulator]

Sounds like she desperately didn’t want to lose you, is she still trying?

Fortunately, no. I think the ghosting served it's intended purpose.

 

[MAD]

Chris Gaines I think.

I see what you did there lol

 

[MAD]

He's a sawed-off little POS. Crazy enough to maybe slash some tires (which he did hers on more than one occasion) but not man enough to come after anybody face to face.

What a rat bastard.

 

[BigOrangeMojo]

Well told story, was hoping it would have gone in a different direction for you.

Part 2

A couple nights later I'm doing a trivia night and up comes this girl who was like "Remember me?". It was zombie girl (without the makeup). She mentioned she broke up with her bf and I was like "I bet our trivia team will do better than yours" and she was like "Your on, what's the bet?". I said if I win, I get a date and she was like " if you win, you get your date but I choose the activity." Well, long story short, I overestimated the intelligence of my team and we got smoked.

After I became 0-2 in bets, she stopped by our table. She was like "I know you are going to Gainesville this weekend so you wanna hang at my apartment tonight for your date (kinda weird since it was a Monday night). I have something in mind that you won't forget." Of course, my 22 year old mind went in the gutter and I was like "sure". Got to her place and I was sitting on the couch. She brought some wine, grapes and strawberries. She said she needed to get something from her room for the date. She brought in a Victoria's Secret bag and handed it to me. I opened the bag and it was...

An unopened Celine Dion DVD concert documentary.

Our date was watching that documentary. It was almost 3 hours long and I fell asleep on the couch. I actually crashed on the couch that night. She woke me up the next morning, gave me some breakfast, and sent me on my way. I was driving back to my place to get ready for work and someone came on the radio and mentioned " A plane has crashed into the tower of the World Trade Center."

That's my where were you 9/11 moment and me still lacking any kind of game.

 

[tbh]

O M G, that is the craziest story. Lol, so funny. This sounds like it could be a SNL skit or something.

It was certainly filed under: "North Florida is a land of oddities". At least the lasagna was palatable, haha.

 

[Regulator]

Part 2

A couple nights later I'm doing a trivia night and up comes this girl who was like "Remember me?". It was zombie girl (without the makeup). She mentioned she broke up with her bf and I was like "I bet our trivia team will do better than yours" and she was like "Your on, what's the bet?". I said if I win, I get a date and she was like " if you win, you get your date but I choose the activity." Well, long story short, I overestimated the intelligence of my team and we got smoked.

After I became 0-2 in bets, she stopped by our table. She was like "I know you are going to Gainesville this weekend so you wanna hang at my apartment tonight for your date (kinda weird since it was a Monday night). I have something in mind that you won't forget." Of course, my 22 year old mind went in the gutter and I was like "sure". Got to her place and I was sitting on the couch. She brought some wine, grapes and strawberries. She said she needed to get something from her room for the date. She brought in a Victoria's Secret bag and handed it to me. I opened the bag and it was...

An unopened Celine Dion DVD concert documentary.

Our date was watching that documentary. It was almost 3 hours long and I fell asleep on the couch. I actually crashed on the couch that night. She woke me up the next morning, gave me some breakfast, and sent me on my way. I was driving back to my place to get ready for work and someone came on the radio and mentioned " A plane has crashed into the tower of the World Trade Center."

That's my where were you 9/11 moment and me still lacking any kind of game.

j/k, btw. There has to be more to this story. It can’t end with a Celine Dion DVD and you crashing on her couch.

 

[MAD]

Part 2

A couple nights later I'm doing a trivia night and up comes this girl who was like "Remember me?". It was zombie girl (without the makeup). She mentioned she broke up with her bf and I was like "I bet our trivia team will do better than yours" and she was like "Your on, what's the bet?". I said if I win, I get a date and she was like " if you win, you get your date but I choose the activity." Well, long story short, I overestimated the intelligence of my team and we got smoked.

After I became 0-2 in bets, she stopped by our table. She was like "I know you are going to Gainesville this weekend so you wanna hang at my apartment tonight for your date (kinda weird since it was a Monday night). I have something in mind that you won't forget." Of course, my 22 year old mind went in the gutter and I was like "sure". Got to her place and I was sitting on the couch. She brought some wine, grapes and strawberries. She said she needed to get something from her room for the date. She brought in a Victoria's Secret bag and handed it to me. I opened the bag and it was...

An unopened Celine Dion DVD concert documentary.

Our date was watching that documentary. It was almost 3 hours long and I fell asleep on the couch. I actually crashed on the couch that night. She woke me up the next morning, gave me some breakfast, and sent me on my way. I was driving back to my place to get ready for work and someone came on the radio and mentioned " A plane has crashed into the tower of the World Trade Center."

That's my where were you 9/11 moment and me still lacking any kind of game.

View attachment 347079

j/k, btw. There has to be more to this story. It can’t end with a Celine Dion DVD and you crashing on her couch.

Oh man, love your storytelling, you got all the build up but not the result we wanted.
@Regulator is right, it can’t just end there.

 

[Regulator]

I also know of this one dude that went on a date with a Puerto Rican chick once and it has cursed the Atlanta Braves franchise ever since.

 

[YankeeVol]

I also know of this one dude that went on a date with a Puerto Rican chick once and it has cursed the Atlanta Braves franchise ever since.

I tell my wife all the time it's her fault the Vols are terrible. We started dating in 2006.

I'm only half joking.

 

[Carl Pickens]

This isn't the worst, but maybe my weirdest for me. Back in the day, I was in a bit of a rut in terms of dating...I was getting more responsibilities at the office, becoming more active in a young professionals group in town, etc. Anyhow, a good buddy of mine convinced me to give the whole internet dating thing a go.

After a couple of uneventful first dates with a few gals that didn't lead to second dates, the next one was a bit...odd. She lived a couple of towns away, but judging from her profile she was relatively cute, had a stable career (librarian), and seemed generally normal after some messaging back and forth. I scoped out a few restaurants in her town online, found an Italian place that, even if things didn't develop with the gal, at least it'd be a good dinner from a food standpoint. So we set up a night to meet up, the veil of normalcy still in place.

At the eatery, I noticed she was a bit more "Goth" than her profile pics let on...not my thing, but hey...I was hungry for some lasagna at any rate. Maybe the conversation would reveal some common ground, right? We talk books and literature for a bit, and she asks if I'd like to know why she's wearing the all-black getup (apparently my expressions made it more obvious than I had thought). She proceeds to tell me that she's heavily involved in a vampire-themed LARPing group in the area and they're meeting up later that night. Apparently they got together and drank "blood" (koolaid or wine) and did fake vampire stuff around a fire from what I gathered. She did extend an invitation which I politely declined. My dinner enjoyment at that point was in decline as I kept imagining her looking at the marinara on her plate in an unsettling way. There was no second date, haha.

You should have told her you’d been noticing blood in your semen lately ..... under the circumstances it might have worked

 

[Carl Pickens]

Part 2

A couple nights later I'm doing a trivia night and up comes this girl who was like "Remember me?". It was zombie girl (without the makeup). She mentioned she broke up with her bf and I was like "I bet our trivia team will do better than yours" and she was like "Your on, what's the bet?". I said if I win, I get a date and she was like " if you win, you get your date but I choose the activity." Well, long story short, I overestimated the intelligence of my team and we got smoked.

After I became 0-2 in bets, she stopped by our table. She was like "I know you are going to Gainesville this weekend so you wanna hang at my apartment tonight for your date (kinda weird since it was a Monday night). I have something in mind that you won't forget." Of course, my 22 year old mind went in the gutter and I was like "sure". Got to her place and I was sitting on the couch. She brought some wine, grapes and strawberries. She said she needed to get something from her room for the date. She brought in a Victoria's Secret bag and handed it to me. I opened the bag and it was...

An unopened Celine Dion DVD concert documentary.

Our date was watching that documentary. It was almost 3 hours long and I fell asleep on the couch. I actually crashed on the couch that night. She woke me up the next morning, gave me some breakfast, and sent me on my way. I was driving back to my place to get ready for work and someone came on the radio and mentioned " A plane has crashed into the tower of the World Trade Center."

That's my where were you 9/11 moment and me still lacking any kind of game.

Celine Dion? I’m surprised you didn’t slash your wrists

 

[Carl Pickens]

Mine wasn’t exactly a date ..., me and two friends were out and ran into two girls we knew. One had just gotten dumped and said she wanted to go party with me so I jumped in the car with her. The other girl went with one of my friends and the other guy called it a night.
I’d had the hots for this girl since jr high and this happened when I was a freshman in college.
She was already pretty intoxicated and had a bottle whiskey so I basically took it from her and drank as much of it as I could to keep her from drinking any more. We ended up parked on a very remote and incredibly dark road a few miles from my house, things got hot and heavy quickly.... she had a short skirt on and was inviting me to the party .... well she says “hold on... I need to pee”.... she gets out so I start messing with the stereo.... I started thinking what the heck is taking so long and got out to check on her.... it was pitch black where we were and I couldn’t see anything.... I looked all around the car and she wasn’t there..., I called her name.... nothing... I called a second time and I heard something that sounded like laughing so I walked towards it and called her name again and she said “I’m down here”.... she had squatted to pee and was so drunk she lost her balance .... fell on her ass and was at the edge of the road and then rolled backwards down into the ditch which was 7-8 ft deep. I went down to get her... had to pull her panties up for her and help her climb back up to the road. I get her back in the car and she proceeds to pass out. Her parents had recently moved and I had no idea where she lived.
I drove to my friend’s house that had already gone home.... knocked on his bedroom window ... he opens the window and I asked him to follow me back out to Hermitage to help me find my other friend and the girl’s friend. He said no.... so I said “then I’m leaving her here in the driveway and walking home.”.... I lived just around the corner....he got pissed but came out and followed me.... I had to pull over at least three times to let her throw up and hold her hair back. Finally found our friends and made sure her friend would get her home.... I had opportunities after that with her, but it never ended up happening. She did thank me though for taking care of her that night

 

[BigOrangeMojo]

Oh man, love your storytelling, you got all the build up but not the result we wanted.
@Regulator is right, it can’t just end there.

Since you all are interested...

PART 3

I did ask zombie girl out for another date (a non Celine Dion documentary date) and she accepted. A day or so before the date she called me and said that her Company had offered her a promotion in Houston and that was going to take that job. She said she didn't want to get into a relationship before she moved so she canceled the date. We met for lunch before she left and drinks one time. We stayed in touch (ha ha, AOL). Right after she moved to Houston, she said that it's a short flight from Memphis to Houston and that I should come down one weekend. By early November, I noticed super cheap plane last minute flight to Houston out of Memphis (and I worked for Hilton Corporate at the time so I could get a cheap hotel room) on a whim for a couple of nights and I booked once I asked if she was going to be in town that weekend.

We met up down there. She met me at the airport and was going to drive me to the hotel. She looked real dolled up. She had indicated that she might not be able to meet up that first night but I was thinking that maybe she switched her plans since you could tell she had spent some time to get ready. On the way to the hotel, she dropped the bomb on me that she was beginning to date a guy and that she had a date after she dropped me off at the hotel. She did say we could meet up for lunch the next day and hang out a while then. We did meet up for lunch and chatted for a long while. Other than that though, it was a lonely weekend in Houston.

Once I got back to Memphis, I started to date and did not communicate nearly as much via AOL. It was a bit of a tough time financially here since Hilton (post 9/11) was struggling and I even sold my tickets to UT-Florida in Gainesville 2001.

 

[MAD]

Mine wasn’t exactly a date ..., me and two friends were out and ran into two girls we knew. One had just gotten dumped and said she wanted to go party with me so I jumped in the car with her. The other girl went with one of my friends and the other guy called it a night.
I’d had the hots for this girl since jr high and this happened when I was a freshman in college.
She was already pretty intoxicated and had a bottle whiskey so I basically took it from her and drank as much of it as I could to keep her from drinking any more. We ended up parked on a very remote and incredibly dark road a few miles from my house, things got hot and heavy quickly.... she had a short skirt on and was inviting me to the party .... well she says “hold on... I need to pee”.... she gets out so I start messing with the stereo.... I started thinking what the heck is taking so long and got out to check on her.... it was pitch black where we were and I couldn’t see anything.... I looked all around the car and she wasn’t there..., I called her name.... nothing... I called a second time and I heard something that sounded like laughing so I walked towards it and called her name again and she said “I’m down here”.... she had squatted to pee and was so drunk she lost her balance .... fell on her ass and was at the edge of the road and then rolled backwards down into the ditch which was 7-8 ft deep. I went down to get her... had to pull her panties up for her and help her climb back up to the road. I get her back in the car and she proceeds to pass out. Her parents had recently moved and I had no idea where she lived.
I drove to my friend’s house that had already gone home.... knocked on his bedroom window ... he opens the window and I asked him to follow me back out to Hermitage to help me find my other friend and the girl’s friend. He said no.... so I said “then I’m leaving her here in the driveway and walking home.”.... I lived just around the corner....he got pissed but came out and followed me.... I had to pull over at least three times to let her throw up and hold her hair back. Finally found our friends and made sure her friend would get her home.... I had opportunities after that with her, but it never ended up happening. She did thank me though for taking care of her that night

Man so, many different thoughts went through my mind as you were telling this story.

 

[MAD]

Since you all are interested...

PART 3

I did ask zombie girl out for another date (a non Celine Dion documentary date) and she accepted. A day or so before the date she called me and said that her Company had offered her a promotion in Houston and that was going to take that job. She said she didn't want to get into a relationship before she moved so she canceled the date. We met for lunch before she left and drinks one time. We stayed in touch (ha ha, AOL). Right after she moved to Houston, she said that it's a short flight from Memphis to Houston and that I should come down one weekend. By early November, I noticed super cheap plane last minute flight to Houston out of Memphis (and I worked for Hilton Corporate at the time so I could get a cheap hotel room) on a whim for a couple of nights and I booked once I asked if she was going to be in town that weekend.

We met up down there. She met me at the airport and was going to drive me to the hotel. She looked real dolled up. She had indicated that she might not be able to meet up that first night but I was thinking that maybe she switched her plans since you could tell she had spent some time to get ready. On the way to the hotel, she dropped the bomb on me that she was beginning to date a guy and that she had a date after she dropped me off at the hotel. She did say we could meet up for lunch the next day and hang out a while then. We did meet up for lunch and chatted for a long while. Other than that though, it was a lonely weekend in Houston.

Once I got back to Memphis, I started to date and did not communicate nearly as much via AOL. It was a bit of a tough time financially here since Hilton (post 9/11) was struggling and I even sold my tickets to UT-Florida in Gainesville 2001.

Man, that sucks big time, I keep hoping your stories would end differently, but I guess all of yours pretty much stick with the theme of worst dates. Also, too bad you missed a hell of a game that year.