Tell Me Your Worst Dating Story?

Carl Pickens

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When I was at UT I lived in an apartment just behind the Pilot on Chapman. Almost every morning I would stop in for pop tarts and a vanilla cappuccino in the winter or pop tarts and a Dr. Pepper in the spring/summer/fall then drive through Vestal to get to campus. One afternoon while getting gas, the manager pulls me to the side and tells me this chick (that he knows) saw me one morning and wanted to know if I was dating anyone. I asked what she looked like and at that time I did not know what "she has a pretty face" meant. So, I give him my number to give her and we talk a few times. We set up a Saturday to go to a rodeo in Seymore or Sevierville (can't remember which). During our conversations she casually mentioned that she had an offer just out of high school to model in London. So, I'm thinking I really have something going on here. I asked where she lived so I can pick her up and she stated she will just meet me at my apartment. Now, I thought she was being smart by not having a stranger know where she lived and become a stalker.

We set up a 6:00 time for her to be there and had planned to go to the Mexican joint in the small outlet/shopping center beside Sonic on Chapman. Well, just about six o'clock I heard a knock on the door and with anticipation I jump up to open it. When I did, I guess my face dropped because her expression was one of embarrassment and I did feel bad. While we were eating I tried everything to talk her into/convince her to to to West Town mall to a movie instead!! I've told this story many times and one of these times a work colleague years ago, before I finished my story, stated "Imma guess she was talking about modeling for Lane Bryant and you wanted to go to a movie because the theatre was dark". He was exactly right. However, I didn't know what Lane Bryant was. Now, the story gets better.

After the rodeo, we get back to my apartment and instead of inviting her in I walk her straight to her car. Very minimal chit chat and then I tell her I have to get to bed. She calls several times over the next couple of weeks and the first few times I answer just to be polite but then I stop. After about the second week, I'm firing up my grill and I hear a vehicle coming down the hill. In my mind I'm thinking it's her but then I think nah, there is no way. I play that game "if I don't look up it wont be her". So, I did not look up! Not even a glance. The car comes down, pulls in front of me, goes into park and then shuts off and I never take my eyes off the grill. The driver gets out, shuts the door and walks right up to me. Sure enough, it was her!

Moral to the story guys, if you are ever set up on a blind date and you are told she has a pretty face, she is going to be a hefty girl!
Did she take the food off your grill before she left or did you feed her the sausage?
 
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volsknx

The only people who dislike winners are losers!
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I have another good ‘un. For about six months, I worked about 150-200 miles from home. During that time, there was a girl that reached out to me through a mutual friend. After talking for a couple of weeks, she decided she was going to make a trip during the week to visit. Now, I am in a very small town with only a Ruby Tuesday as upscaled restaurant and a local place. I did not know anything about it either but that is where she decides we are going to go. We get there and naturally, I look at the most expensive thing on the menu. Then, low and behold, this heavy set chick decides to order that exact thing! The whole time we are there she is talking. It is not just that it is non stop but this chick is loud as hell! I am soooo embarrassed! The only thing saving me is that as I am not from there, I know absolutely no one! To match that, she actually tries to be condescending and negative towards me and about me.

That was the second worse date I have ever been on!
 

mad4vols

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I have another good ‘un. For about six months, I worked about 150-200 miles from home. During that time, there was a girl that reached out to me through a mutual friend. After talking for a couple of weeks, she decided she was going to make a trip during the week to visit. Now, I am in a very small town with only a Ruby Tuesday as upscaled restaurant and a local place. I did not know anything about it either but that is where she decides we are going to go. We get there and naturally, I look at the most expensive thing on the menu. Then, low and behold, this heavy set chick decides to order that exact thing! The whole time we are there she is talking. It is not just that it is non stop but this chick is loud as hell! I am soooo embarrassed! The only thing saving me is that as I am not from there, I know absolutely no one! To match that, she actually tries to be condescending and negative towards me and about me.

That was the second worse date I have ever been on!
Lol, Ruby Tuesday was the upscale restaurant. Loved that part.
 
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Carl Pickens

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I have another good ‘un. For about six months, I worked about 150-200 miles from home. During that time, there was a girl that reached out to me through a mutual friend. After talking for a couple of weeks, she decided she was going to make a trip during the week to visit. Now, I am in a very small town with only a Ruby Tuesday as upscaled restaurant and a local place. I did not know anything about it either but that is where she decides we are going to go. We get there and naturally, I look at the most expensive thing on the menu. Then, low and behold, this heavy set chick decides to order that exact thing! The whole time we are there she is talking. It is not just that it is non stop but this chick is loud as hell! I am soooo embarrassed! The only thing saving me is that as I am not from there, I know absolutely no one! To match that, she actually tries to be condescending and negative towards me and about me.

That was the second worse date I have ever been on!
Did she fart out loud too?
 

BigOrangeMojo

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I have another good ‘un. For about six months, I worked about 150-200 miles from home. During that time, there was a girl that reached out to me through a mutual friend. After talking for a couple of weeks, she decided she was going to make a trip during the week to visit. Now, I am in a very small town with only a Ruby Tuesday as upscaled restaurant and a local place. I did not know anything about it either but that is where she decides we are going to go. We get there and naturally, I look at the most expensive thing on the menu. Then, low and behold, this heavy set chick decides to order that exact thing! The whole time we are there she is talking. It is not just that it is non stop but this chick is loud as hell! I am soooo embarrassed! The only thing saving me is that as I am not from there, I know absolutely no one! To match that, she actually tries to be condescending and negative towards me and about me.

That was the second worse date I have ever been on!
Speaking from my experience earlier in the thread, guys will tolerate a bunch of stuff if the girl is fit and attractive. If the girl is heavy set, guys barely tolerate anything.
 

davethevol

Don’t hate me because I’m beautiful......
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I went on a blind date with a girl to a beer fest. She got hammered and at one point told me I looked just like Pee Wee Herman (I don’t look anything like him and the only thing I could think of that would be similar is I had a buzz cut at the time). So I offered to get another beer and used that chance to just sneak off and meet up with some friends that were there.
 

mad4vols

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I went on a blind date with a girl to a beer fest. She got hammered and at one point told me I looked just like Pee Wee Herman (I don’t look anything like him and the only thing I could think of that would be similar is I had a buzz cut at the time). So I offered to get another beer and used that chance to just sneak off and meet up with some friends that were there.
14558E06-4356-4E28-9404-7AF66D7FE29E.png
 
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Aesius

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Very first date I ever went on. I was 16 and she was 15. She gave me her address, which ended up being in a trailer park. Okay, not great, but I can deal with it.

Then I had to go inside and meet the parents. We proceeded to watch TV together for HOURS while her mom stared at me. Finally, we got the green light to leave and the date started, and I quickly realized we had ZERO chemistry. Our interactions were horribly awkward and unpleasant. I would crack a joke and she would get mad. But being young and inexperienced, I kept trying to make the date work, which just made things worse.

But of course, youth and inexperience meant I still didn't learn my lesson even after a painful afternoon, and we proceeded to go out a few more times, each of which was just as awkward and painful. Then, after breaking up with my long-term high school girlfriend a few years later, the bad date girl looked me up and we went out AGAIN....and it was just as awful as it had been years prior.
 

peaygolf

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My 1st post was true..........

But the single worst date: I just got sober and went on a date at about 4 months. She pounded 5 Vodka Tonics before dinner was served..............I left a $100 bill for her to pay and an Uber home and bolted!
 
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BigOrangeMojo

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I went on a blind date with a girl to a beer fest. She got hammered and at one point told me I looked just like Pee Wee Herman (I don’t look anything like him and the only thing I could think of that would be similar is I had a buzz cut at the time). So I offered to get another beer and used that chance to just sneak off and meet up with some friends that were there.
Disappointed you didnt say "Wanna go back to my Playhouse and see my Big Adventure?"
 

Hurley Mooncalf

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Back in the days of early internet, I was chatting with a girl and was getting to the point where we discussed about going out. This would have been when you would have to scan a picture onto a computer, pre digital camera days so I hadn't seen a pic of her but she described herself as athletic and fit. She also had talked about different aerobic activities she was into so I decided to drop by the department she worked at on a day I knew she would be there to scope it out since she wouldn't know me from Adam so I could see what she looked like. I went in and make my way around the store. There's probably 8-10 women working and quite frankly, they were all pretty attractive if they were in her age range. Then I made my way to checkout and she was the cashier. Man, she was huge. Literally, every girl in there was hot except her. She tried to chat me up online and I was upfront with her that she hadn't been honest about her appearance and that it would not work. She said "you're just like most other guys". I responded with something on the lines of yeah, most guys don't like liars.
 

mad4vols

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Back in the days of early internet, I was chatting with a girl and was getting to the point where we discussed about going out. This would have been when you would have to scan a picture onto a computer, pre digital camera days so I hadn't seen a pic of her but she described herself as athletic and fit. She also had talked about different aerobic activities she was into so I decided to drop by the department she worked at on a day I knew she would be there to scope it out since she wouldn't know me from Adam so I could see what she looked like. I went in and make my way around the store. There's probably 8-10 women working and quite frankly, they were all pretty attractive if they were in her age range. Then I made my way to checkout and she was the cashier. Man, she was huge. Literally, every girl in there was hot except her. She tried to chat me up online and I was upfront with her that she hadn't been honest about her appearance and that it would not work. She said "you're just like most other guys". I responded with something on the lines of yeah, most guys don't like liars.
Excellent comeback to her comment.
 
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Vegas_Ferguson

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May be tl;dr it ranks as a worst post-date story.

Mid-1980s. I'm a sophomore in high school. Dad acquired, through means never made clear, a 1976 cherry red Corvette. Mint and magnificent. Father Ferguson kept it hidden and covered in a single car garage behind our house. He would occasionally take Mother Ferguson out for a spin on weekends. Us kids were told in no uncertain terms, “Do not touch.” Knowing my lean toward mischief, FF told me this more than once. Well, how CAN a man resist such temptation?

I usually had a couple hours between whatever sports season practice was happening to make my way three blocks from school to our house. I saw no harm in lifting dad’s keys (kept in a cigar box in his closet) for a bit of cruising. Rumor had it such a vehicle made a favorable impression on girls. Yes, girls took notice. And rides. This went on for a couple weeks.

My younger sister nearest my age found out and told me, “Dad will kill you!”
“He’ll never know” I said, choosing to remain oblivious to something called an odometer.

The pinnacle of this pre-Uber adventure came when I talked a junior class cheerleader / Valerie Bertinelli look-a-like into some serious make-out time while parked under a tree near school. No easy feat in that vehicle. I get her number and drop her off at her house. Return to stash the car on top of the world because I’m the ****ing king, you see.

An alleyway ran behind the houses of our neighborhood. You could access the garage without drawing notice. I cut to stash the car as usual when I see that the garage doors were open. I had closed and locked them. Always did. My head spins to the left to see Father Ferguson’s work truck parked in our driveway. My field of vision also picks up a familiar figure in our backyard. There stood Father Ferguson with a beer in one hand, cigarette in the other. He gives me a sinister smile and wave as I cruise by.

“Nice car!” he yells.

It is here, dear reader, the memory gets a bit dim. Somehow, I got the car back in the garage and came to Jesus during a loooooooong walk to the house. Come in the backdoor and into our kitchen. Dad stood there watching this old B/W TV we kept on the counter. Without raising his voice or even blinking, he says, “Gimme the ****ing keys, Mac.”

I gave him the ****ing keys. The next several minutes were…unpleasant. Turns out, he knew someone was joyriding. He wanted to catch the thief cherry red handed.

Epilogue: Week later we’re driving to one of his construction jobs. My penitence included free labor for him. Crossing the street walks Valerie. She smiles and waves.

“One of your taxi fares?” He asks sarcastically.
Yea, I reply. He says, Well, you’re doing it right. Then he laughs that crazed tipsy laugh of his and hits me on the shoulder. I laugh, too.
 
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mad4vols

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May be tl;dr it ranks as a worst post-date story.

Mid-1980s. I'm a sophomore in high school. Dad acquired, through means never made clear, a 1976 cherry red Corvette. Mint and magnificent. Father Ferguson kept it hidden and covered in a single car garage behind our house. He would occasionally take Mother Ferguson out for a spin on weekends. Us kids were told in no uncertain terms, “Do not touch.” Knowing my lean toward mischief, FF told me this more than once. Well, how CAN a man resist such temptation?

I usually had a couple hours between whatever sports season practice was happening to make my way three blocks from school to our house. I saw no harm in lifting dad’s keys (kept in a cigar box in his closet) for a bit of cruising. Rumor had it such a vehicle made a favorable impression on girls. Yes, girls took notice. And rides. This went on for a couple weeks.

My younger sister nearest my age found out and told me, “Dad will kill you!”
“He’ll never know” I said, choosing to remain oblivious to something called an odometer.

The pinnacle of this pre-Uber adventure came when I talked a junior class cheerleader / Valerie Bertinelli look-a-like into some serious make-out time while parked under a tree near school. No easy feat in that vehicle. I get her number and drop her off at her house. Return to stash the car on top of the world because I’m the ****ing king, you see.

An alleyway ran behind the houses of our neighborhood. You could access the garage without drawing notice. I cut to stash the car as usual when I see that the garage doors were open. I had closed and locked them. Always did. My head spins to the left to see Father Ferguson’s work truck parked in our driveway. My field of vision also picks up a familiar figure in our backyard. There stood Father Ferguson with a beer in one hand, cigarette in the other. He gives me a sinister smile and wave as I cruise by.

“Nice car!” he yells.

It is here, dear reader, the memory gets a bit dim. Somehow, I got the car back in the garage and came to Jesus during a loooooooong walk to the house. Come in the backdoor and into our kitchen. Dad stood there watching this old B/W TV we kept on the counter. Without raising his voice or even blinking, he says, “Gimme the ****ing keys, Mac.”

I gave him the ****ing keys. The next several minutes were…unpleasant. Turns out, he knew someone was joyriding. He wanted to catch the thief cherry red handed.

Prologue: Week later we’re driving to one of his construction jobs. My penitence included free labor for him. Crossing the street walks Valerie. She smiles and waves.

“One of your taxi fares?” He asks sarcastically.
Yea, I reply. He says, Well, you’re doing it right. Then he laughs that crazed tipsy laugh of his and hits me on the shoulder. I laugh, too.
Lol, had me cracking up. You are an excellent writer and storyteller.
 
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Carl Pickens

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I went on a blind date with a girl to a beer fest. She got hammered and at one point told me I looked just like Pee Wee Herman (I don’t look anything like him and the only thing I could think of that would be similar is I had a buzz cut at the time). So I offered to get another beer and used that chance to just sneak off and meet up with some friends that were there.
You should have said .... “oh yeah?.... well you look like a bucket of S” 😎
 

mad4vols

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My 1st post was true..........

But the single worst date: I just got sober and went on a date at about 4 months. She pounded 5 Vodka Tonics before dinner was served..............I left a $100 bill for her to pay and an Uber home and bolted!
Being married to an alcoholic for many years, you made a smart decision.
 

mad4vols

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Very first date I ever went on. I was 16 and she was 15. She gave me her address, which ended up being in a trailer park. Okay, not great, but I can deal with it.

Then I had to go inside and meet the parents. We proceeded to watch TV together for HOURS while her mom stared at me. Finally, we got the green light to leave and the date started, and I quickly realized we had ZERO chemistry. Our interactions were horribly awkward and unpleasant. I would crack a joke and she would get mad. But being young and inexperienced, I kept trying to make the date work, which just made things worse.

But of course, youth and inexperience meant I still didn't learn my lesson even after a painful afternoon, and we proceeded to go out a few more times, each of which was just as awkward and painful. Then, after breaking up with my long-term high school girlfriend a few years later, the bad date girl looked me up and we went out AGAIN....and it was just as awful as it had been years prior.
Sorry, couldn’t stop laughing at the part where you said her mom was just staring at you 🤣😂🤣
 

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