Worst Date Ever

DGS49

Diamond Member
Apr 12, 2012
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Pittsburgh
It's 1965, I'm a 15-year-old HS Sophomore. On the way to school on a Friday morning (we walked to school), my friends and I are having our usual stupid conversations, and we encounter a small group of girls on the same sidewalk going the opposite way. (We are headed to the all-boys Catholic HS, they are headed to the all-girls counterpart).

One of the girls that I knew from grade school (Lynn), called out to me and indicated she wanted to have a private conversation. Out of the blue. She tells me that her "best friend" had a catastrophic development a few days ago. She broke up with her long-term boyfriend a couple days before the Senior Prom. She already had her prom dress, etc., etc., etc. "What does this have to do with me?"

"She needs a last-minute date." I vigorously protest. I am totally broke. I don't even own a suit, let alone have the money to rent a tux (or whatever it's called), I can't pay for anything. NO PROBLEM, I'm told. Everything is taken care of. And of course I've never even heard of this girl, let along knew her. I was going to reject the idea out of hand, when Lynn told me that I would be double-dating with her and her boyfriend, Harry, and he was a very cool Senior. Well, at least the evening would be entertaining if we were with Harry. So I agreed to do it. My best clothing was a herringbone sport coat, black pants, white shirt and I could borrow a nice tie from my dad.

Harry shows up at my house at the appointed time (he didn't know where I lived). As soon as he sees me, he says something to the effect of, "So YOU'RE the one they roped into this!" My first indication that this was going to be a bad, bad evening. We went to pick up Lynn, then off to pick up my date, whose name was Roseanna, as I recall. Lynn gave me a corsage, to give to my date.

When we got to the house to pick her up, a few things became clear. There was no boyfriend, no breakup, and Roseanna's family thought that I was her boyfriend - "Glad to finally meet you," and all that. Of course, I didn't consciously do anything to expose her deception, and in fact I tried my best to make the most of it. I was a typically shallow teenage boy, and was disappointed but not surprised that she was not terribly pretty and she was a bit overweight. We did the usual prom stuff, dancing and socializing. Because it was a Senior Prom and I was only a Sophomore, I took a bit of ribbing, but that was just part of the whole lovely experience. Roseanna and I were photographed together, the pictures being posted on the Bulletin Board at their school on the following Monday, a spectacle that did not go over well with a girl that I was starting to woo at the time.

After the Prom, "we" were invited to an after-prom party, which in our culture was an opportunity to get to second and third base, so to speak. But continuing that metaphor, I chose an intentional walk, telling the car's three other occupants that I had to get home to watch Lawrence Welk with my family. I said the obligatory things when they dropped me off, and Lynn thanked me profusely as I was getting out. Harry bast my balls about the whole thing for the next couple months, and of course many of my male and female friends also had laughs at my expense. Funny, I never saw Lynn again. I guess she started going a different route to school in the morning.

Anyone else care to share their Worst Date story?
 
It's 1965, I'm a 15-year-old HS Sophomore. On the way to school on a Friday morning (we walked to school), my friends and I are having our usual stupid conversations, and we encounter a small group of girls on the same sidewalk going the opposite way. (We are headed to the all-boys Catholic HS, they are headed to the all-girls counterpart).

One of the girls that I knew from grade school (Lynn), called out to me and indicated she wanted to have a private conversation. Out of the blue. She tells me that her "best friend" had a catastrophic development a few days ago. She broke up with her long-term boyfriend a couple days before the Senior Prom. She already had her prom dress, etc., etc., etc. "What does this have to do with me?"

"She needs a last-minute date." I vigorously protest. I am totally broke. I don't even own a suit, let alone have the money to rent a tux (or whatever it's called), I can't pay for anything. NO PROBLEM, I'm told. Everything is taken care of. And of course I've never even heard of this girl, let along knew her. I was going to reject the idea out of hand, when Lynn told me that I would be double-dating with her and her boyfriend, Harry, and he was a very cool Senior. Well, at least the evening would be entertaining if we were with Harry. So I agreed to do it. My best clothing was a herringbone sport coat, black pants, white shirt and I could borrow a nice tie from my dad.

Harry shows up at my house at the appointed time (he didn't know where I lived). As soon as he sees me, he says something to the effect of, "So YOU'RE the one they roped into this!" My first indication that this was going to be a bad, bad evening. We went to pick up Lynn, then off to pick up my date, whose name was Roseanna, as I recall. Lynn gave me a corsage, to give to my date.

When we got to the house to pick her up, a few things became clear. There was no boyfriend, no breakup, and Roseanna's family thought that I was her boyfriend - "Glad to finally meet you," and all that. Of course, I didn't consciously do anything to expose her deception, and in fact I tried my best to make the most of it. I was a typically shallow teenage boy, and was disappointed but not surprised that she was not terribly pretty and she was a bit overweight. We did the usual prom stuff, dancing and socializing. Because it was a Senior Prom and I was only a Sophomore, I took a bit of ribbing, but that was just part of the whole lovely experience. Roseanna and I were photographed together, the pictures being posted on the Bulletin Board at their school on the following Monday, a spectacle that did not go over well with a girl that I was starting to woo at the time.

After the Prom, "we" were invited to an after-prom party, which in our culture was an opportunity to get to second and third base, so to speak. But continuing that metaphor, I chose an intentional walk, telling the car's three other occupants that I had to get home to watch Lawrence Welk with my family. I said the obligatory things when they dropped me off, and Lynn thanked me profusely as I was getting out. Harry bast my balls about the whole thing for the next couple months, and of course many of my male and female friends also had laughs at my expense. Funny, I never saw Lynn again. I guess she started going a different route to school in the morning.

Anyone else care to share their Worst Date story?
Never go on a blind date.
 
It's 1965, I'm a 15-year-old HS Sophomore. On the way to school on a Friday morning (we walked to school), my friends and I are having our usual stupid conversations, and we encounter a small group of girls on the same sidewalk going the opposite way. (We are headed to the all-boys Catholic HS, they are headed to the all-girls counterpart).

One of the girls that I knew from grade school (Lynn), called out to me and indicated she wanted to have a private conversation. Out of the blue. She tells me that her "best friend" had a catastrophic development a few days ago. She broke up with her long-term boyfriend a couple days before the Senior Prom. She already had her prom dress, etc., etc., etc. "What does this have to do with me?"

"She needs a last-minute date." I vigorously protest. I am totally broke. I don't even own a suit, let alone have the money to rent a tux (or whatever it's called), I can't pay for anything. NO PROBLEM, I'm told. Everything is taken care of. And of course I've never even heard of this girl, let along knew her. I was going to reject the idea out of hand, when Lynn told me that I would be double-dating with her and her boyfriend, Harry, and he was a very cool Senior. Well, at least the evening would be entertaining if we were with Harry. So I agreed to do it. My best clothing was a herringbone sport coat, black pants, white shirt and I could borrow a nice tie from my dad.

Harry shows up at my house at the appointed time (he didn't know where I lived). As soon as he sees me, he says something to the effect of, "So YOU'RE the one they roped into this!" My first indication that this was going to be a bad, bad evening. We went to pick up Lynn, then off to pick up my date, whose name was Roseanna, as I recall. Lynn gave me a corsage, to give to my date.

When we got to the house to pick her up, a few things became clear. There was no boyfriend, no breakup, and Roseanna's family thought that I was her boyfriend - "Glad to finally meet you," and all that. Of course, I didn't consciously do anything to expose her deception, and in fact I tried my best to make the most of it. I was a typically shallow teenage boy, and was disappointed but not surprised that she was not terribly pretty and she was a bit overweight. We did the usual prom stuff, dancing and socializing. Because it was a Senior Prom and I was only a Sophomore, I took a bit of ribbing, but that was just part of the whole lovely experience. Roseanna and I were photographed together, the pictures being posted on the Bulletin Board at their school on the following Monday, a spectacle that did not go over well with a girl that I was starting to woo at the time.

After the Prom, "we" were invited to an after-prom party, which in our culture was an opportunity to get to second and third base, so to speak. But continuing that metaphor, I chose an intentional walk, telling the car's three other occupants that I had to get home to watch Lawrence Welk with my family. I said the obligatory things when they dropped me off, and Lynn thanked me profusely as I was getting out. Harry bast my balls about the whole thing for the next couple months, and of course many of my male and female friends also had laughs at my expense. Funny, I never saw Lynn again. I guess she started going a different route to school in the morning.

Anyone else care to share their Worst Date story?
Yeah, but you know what's nice about that night? Rosanna will always remember it fondly...
Good job.
 
I'll try the condensed version. It's about '99 and I meet this gal online, she's from Toronto. I'm in Dallas. I'm well-traveled, worked and lived out of the States most of the time, so Canada is no challenge. I'm actually designing and selling hydraulic equipment to the govt of Turkey. One of the large components was in Syracuse, NY. I needed to go up and inspect it and sign off on it. We've been pretty intimate on the phone for several months. She got my pics online and sent me a shoebox of her pics. In '99 that wasn't too suspicious, image files weren't as readily exchanged as they are now. I tell her I'll be close to her in Toronto soon and I'll drive over from Syracuse after my business is concluded. The awkward silence was deafening. I knew something was wrong.

Anyway, I do my business in NY and call her as I'm driving to Toronto. I had reserved a nice hotel room. Figured we consummate this thing and who knows after that. She's ends up being late meeting me at the hotel by at least 30 minutes. Eventually I see this wildebeest get out of 25-year old F-150 and it takes a few seconds for the springs to level out. If normal hair density is 1, she had a hair density of .05. Round numbers, she was 4'10", 170 lbs.

I lost my shit, and was out of there in less than a minute. I ended up driving to Niagara Falls and staring at it for hours wondering why God was fucking me. That was a teachable moment.... it never happened again. ;)
 
For me, it was about 1985. I was 20.
A past girlfriend called me up and said her friend saw a photo of mine and wanted to go out.
My GF was attractive, and many times pretty girls are friends with other pretty girls. But i was still skeptical. So I said I would only go out with her if I saw a photo of her. Se we met in a parking lot, and presented me with the photo. A pretty red head. Nice face.
So I agreed to go. I meet her, and I am immediately feeling swindled.
The girl is a red head. But she is not the girl in the photo. Not very close at all.
 

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