The most awkward date you have ever had in your lifetime?

My best friend fixed me up with a blind date. When the guy showed up to pick me up, he came about up to my chest. He told me that he was a jockey. I am very tall! We were going dancing! He liked tall womenšŸ˜±. I was gracious and pleasant on the date but it was very uncomfortable for me.
 

I met a girl in my beginning Chemistry class in college. Over the first few weeks of class I noticed a nice-looking young lady. Over the following weeks we began to talk a bit and eventually I asked her out on a date, dinner and a movie. She accepted but said "we first had to go to a service at her church". A bit weird I thought, but not a problem. I have attended services at many different church denominations. Later in the week, when I went over to pick her up, she mentioned that she was a Southern Baptist.

We went in the church and sit down about 1/4 of the way from the front of the church. When the minister came out, he started out with a prayer and a song. It was all very familiar, no problem! Then he slowly stepped forward looking over the congregation and started yelling at the top of his lungs. He focused in on a young woman with a very young child. The child had been fussing and crying during the prayer. He went on to tell the young lady that the "devil" was in that child, and it was her Christian duty to beat that devil out of that child. He then started saying terrible things about how bad of a mother she is and that she will go to he_ _ if she doesn't change her ways. I WAS SHOCKED! Yet as I looked around know body else seemed surprised or upset by the yelling and the comments.

The minister yelled and stomped around on that stage for the whole sermon, saying things to the people in the church that were strong and sometimes downright crazy, from my perspective. I hung in for the whole thing so we could go on our date. I guarantee you I no longer had any interest in this girl, did not even want to touch her. Of course, at 19 things can change. To my complete surprise when we got out on the date this girl was all over me, it was really something, and she really was a nice-looking girl. But I ended up taking her home early, we got something to eat and then home. That was the weirdest date yet.
 

I think I wrote about another one here already, but maybe not this one:

I lived in another country. A male student invited me for coffee. I knew he didn't have designs on me himself. A friend of his was with him in the coffee shop, which was fine. (I really can't remember whether he'd said his friend would be joining us.)

We talked about this and that, and the friend mentioned that he was divorced. I thought nothing of it.

Then he asked me why I was divorced. I said that was personal, and asked why he would ask me such a question.

He said, "I'm looking for a girlfriend, and I want to know what kind of person you are."

Maybe I should have known my student was introducing us as a potential couple, but I had no idea.

In that same country, married men would ask me to be their "girlfriend." They didn't even try to hide that they were married. One even asked me (in VERY broken English) in front of his son, who was about 5.
 
I had been out with this fellow for about 3 months and he never kissed me or tried anything. My mom liked him and I liked him too, not like wow, but I liked him. We were both in our twenties. Finally, ( it was not comfortable to do) I asked him didn't he want to kiss and he did not want to talk about it. He never called me back. I often wondered if he turned out to be more interested in men.
 
So I went on a double date with a buddy of mine, we went parking, he was in the front seat with his date, and I in the back seat with mine. After a bit of making out, he says, "Hey, let's do something crazy, let's switch off". So his date climbed in back with me, and mine got in front with him. It was weird and awkward, but crazy things happen. I ended up marrying her after several years. Here's a pic after our son was born.Our young family pic.jpg
 
In my 20's and had known of the girl but nothing really much about her except she was cute.
Was a small town. Everybody knows of everyone.

Invited her to my house one evening for a steak dinner I would prepare.
While the charcoal grill was getting ready, I began to boil potatoes.
She'd said she preferred mashed potatoes over baked. Alrighty, no problem.
She also instructed me not to mash the potatoes when done ... she'd do that. That's nice.

She walked outside.

Few minutes later, I went outside to check on the grill and saw she was next door talking to my neighbor.
I set the table, fixed the salad ... the steaks were almost done ... she was still talking to my neighbor.
Since she was busy and steak was almost ready to eat, I mashed the potatoes.

I yelled, "Hey Deb, supper is ready." and she walked back to my house a "few" minutes later.

The plates were fixed. Steak was getting cold ... and she raised her voice and started berating me.

I TOLD YOU I WAS GOING TO MASH THE POTATOES !!! BLAH BLAH BLAH this and BLAH BLAH that.
Why this and why that and so forth and so on. On and on like I was a child or something and had misbehaved severely.

There wasn't much conversation during the meal other than me apologizing for the potatoes.
I may as well have been apologizing TO the potatoes. She ate everything on her plate.

The night was young and I'd planned on maybe a movie, somewhere in town for drinks, whatever.
Finishing the meal, I said, "Let me walk you to your car." ... "Good night" ~~~

Truly the most weird, awkward part was eating mashed instead of baked potato with a steak. Weird.
 
Naturally said:
In my 20's and had known of the girl but nothing really much about her except she was cute.
Was a small town. Everybody knows of everyone.

Invited her to my house one evening for a steak dinner I would prepare.
While the charcoal grill was getting ready, I began to boil potatoes.
She'd said she preferred mashed potatoes over baked. Alrighty, no problem.
She also instructed me not to mash the potatoes when done ... she'd do that. That's nice.

She walked outside.

Few minutes later, I went outside to check on the grill and saw she was next door talking to my neighbor.
I set the table, fixed the salad ... the steaks were almost done ... she was still talking to my neighbor.
Since she was busy and steak was almost ready to eat, I mashed the potatoes.

I yelled, "Hey Deb, supper is ready." and she walked back to my house a "few" minutes later.

The plates were fixed. Steak was getting cold ... and she raised her voice and started berating me.

I TOLD YOU I WAS GOING TO MASH THE POTATOES !!! BLAH BLAH BLAH this and BLAH BLAH that.
Why this and why that and so forth and so on. On and on like I was a child or something and had misbehaved severely.

There wasn't much conversation during the meal other than me apologizing for the potatoes.
I may as well have been apologizing TO the potatoes. She ate everything on her plate.

The night was young and I'd planned on maybe a movie, somewhere in town for drinks, whatever.
Finishing the meal, I said, "Let me walk you to your car." ... "Good night" ~~~

Truly the most weird, awkward part was eating mashed instead of baked potato with a steak. Weird.
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@ Naturally, well at least she ate the potatoes though. Great date story LOL
 
Well, there was also the date where we were to meet up at a bike trail and have a ride, with breakfast afterward. I had told the guy that while I greatly enjoyed riding my bike, I wasn't a fast rider or a great distance rider, and I just had an old 5-speed bike that I tooled along on.

He said, no problem...we'd tool along at my speed.

I show up first, wearing my usual gear, t-shirt, shorts, tennies and a ball cap. He shows up with a very expensive bike, dressed in his racing outfit with a helmet that made him look like an alien. We start out and it's obvious right away that he's annoyed by having to keep to my speed. So I said, go ahead and ride like you want. You can go to the end and come back and when I reach my limit, I'll turn back and we'll meet up somewhere along the trail and then go to breakfast. He agreed.

So I tootle along the trail and turn back when I'm ready, expecting any minute for him to come up behind me. I get back to the parking area and his car is gone. He apparently had taken an alternate route back, beat me back to the parking area, packed up and gone. Never heard from him again.

What a coward.
 
jujube said:
Well, there was also the date where we were to meet up at a bike trail and have a ride, with breakfast afterward. I had told the guy that while I greatly enjoyed riding my bike, I wasn't a fast rider or a great distance rider, and I just had an old 5-speed bike that I tooled along on.

He said, no problem...we'd tool along at my speed.

I show up first, wearing my usual gear, t-shirt, shorts, tennies and a ball cap. He shows up with a very expensive bike, dressed in his racing outfit with a helmet that made him look like an alien. We start out and it's obvious right away that he's annoyed by having to keep to my speed. So I said, go ahead and ride like you want. You can go to the end and come back and when I reach my limit, I'll turn back and we'll meet up somewhere along the trail and then go to breakfast. He agreed.

So I tootle along the trail and turn back when I'm ready, expecting any minute for him to come up behind me. I get back to the parking area and his car is gone. He apparently had taken an alternate route back, beat me back to the parking area, packed up and gone. Never heard from him again.

What a coward.
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What a jackass. I guess it's best that you found that out right away before investing any more time with him.
 
Naturally said:
In my 20's and had known of the girl but nothing really much about her except she was cute.
Was a small town. Everybody knows of everyone.

Invited her to my house one evening for a steak dinner I would prepare.
While the charcoal grill was getting ready, I began to boil potatoes.
She'd said she preferred mashed potatoes over baked. Alrighty, no problem.
She also instructed me not to mash the potatoes when done ... she'd do that. That's nice.

She walked outside.

Few minutes later, I went outside to check on the grill and saw she was next door talking to my neighbor.
I set the table, fixed the salad ... the steaks were almost done ... she was still talking to my neighbor.
Since she was busy and steak was almost ready to eat, I mashed the potatoes.

I yelled, "Hey Deb, supper is ready." and she walked back to my house a "few" minutes later.

The plates were fixed. Steak was getting cold ... and she raised her voice and started berating me.

I TOLD YOU I WAS GOING TO MASH THE POTATOES !!! BLAH BLAH BLAH this and BLAH BLAH that.
Why this and why that and so forth and so on. On and on like I was a child or something and had misbehaved severely.

There wasn't much conversation during the meal other than me apologizing for the potatoes.
I may as well have been apologizing TO the potatoes. She ate everything on her plate.

The night was young and I'd planned on maybe a movie, somewhere in town for drinks, whatever.
Finishing the meal, I said, "Let me walk you to your car." ... "Good night" ~~~

Truly the most weird, awkward part was eating mashed instead of baked potato with a steak. Weird.
Click to expand...
Arn't you glad you didn't marry her?
 
This thread got me to thinking. I've never had an actual (ask you out) date. So, does this count?
The only time I ever asked a girl out happened not long after I got back from Vietnam. I was living in my hearse and met this girl working at a Friendly's ice creme shop. Asked her to go to an Allman brothers concert with me and she agreed. I bought the best tickets they had and to lesson the shock to her parents, I borrowed my friend Gordon's 4 door mercury montego. (figured some dad's wouldn't take kindly to their daughter going off in a hearse). I showed up at the door and was greeted by her mother who told me she had left to party some friends for the evening. ????
I was crushed, so I brought back the Merc, gave Gordon the tickets and climbed into my hearse and drove to my favorite bar. (Cy's Place) where I proceeded to drink Southern Comfort Manhattans until I could barely stand. Staggered out to the hearse and climbed in back to get a little sleep. I guess it scared some folks who came up to the hearse and looking in the side window, saw me stretched out because they called the law. I woke up to a cop thumping the window (I think to break it) and a crowd of people hanging around. Only took a minute to clear it up and the officer even thanked me for not driving drunk.
 
It was our first date, but we'd met before. I worked with her brother and she brought him lunch a couple times, to the work site. He told me she thought I was cute and I should ask her out.

So anyway, I took her to our small town's hottest (and only) club for drinks and dancing. Lots of drinks and dances later, I'm sitting at a table chatting with her, and we're laughing our butts off and having a good ol' time, except the girt at this table isn't my date. I'd sat at the wrong table.

I was so sloshed, I didn't realize the girl I'd sat with, talked to and laughed with for at least 10 minutes was not my date ...until my actual date tapped me on the shoulder and said "You need to pay for my cab."

I gave her a $20. I apologized, but that was useless. She gave me this "Yeah, right" look. Understandably.
 
When I was much younger, I dated a girl from another college who I didn't know very well. She liked the idea of going out with a Cadet from the Naval Academy and so she invited me to the wedding of her cousin. She was under the impression that I would be wearing my dress uniform, which I didn't. I wore a plain dark gray suit, white shirt and a black and blue tie with red highlights. (and sunglasses)

Since she was under the impression that I would be wearing my dress uniform, she wore a gown, which to me seemed gaudy to begin with and when I first saw it on her, I was kind of embarrassed for the both of us. After she saw I had a normal dress suit on she asked me why didn't I wear my dress uniform. I told her that I had called the groom, which also introduced us to each other, and asked him if I should wear my dress uniform. He said it wasn't necessary. At that point, she went on about her Uncle, who was also in the military as a lifer and wore his dress uniform to all social events.

Cut to the chase here, but after several words between us and back and forth, she decided she wasn't going and told me that "You may as well go home." I did and that was that. I had heard later that she changed clothes and did go to the wedding, which I kind of thought she would since it was her cousin. Later, I also thought that if she wanted me to wear my dress uniform, maybe she should have asked me, but then I also thought maybe I should have asked her as well. It was just a mix up in communications, but was awkward.
 
squatting dog said:
This thread got me to thinking. I've never had an actual (ask you out) date. So, does this count?
The only time I ever asked a girl out happened not long after I got back from Vietnam. I was living in my hearse and met this girl working at a Friendly's ice creme shop. Asked her to go to an Allman brothers concert with me and she agreed. I bought the best tickets they had and to lesson the shock to her parents, I borrowed my friend Gordon's 4 door mercury montego. (figured some dad's wouldn't take kindly to their daughter going off in a hearse). I showed up at the door and was greeted by her mother who told me she had left to party some friends for the evening. ????
I was crushed, so I brought back the Merc, gave Gordon the tickets and climbed into my hearse and drove to my favorite bar. (Cy's Place) where I proceeded to drink Southern Comfort Manhattans until I could barely stand. Staggered out to the hearse and climbed in back to get a little sleep. I guess it scared some folks who came up to the hearse and looking in the side window, saw me stretched out because they called the law. I woke up to a cop thumping the window (I think to break it) and a crowd of people hanging around. Only took a minute to clear it up and the officer even thanked me for not driving drunk.
Click to expand...
Wait! You were driving a hearse and going to a Allman Brothers concert, went to a bar, got drunk and fell asleep in back of the hearse only to be awakened by a cop. Now, that's going to be hard to top.
 
LoL. My buds fixed me up with "MJ", aka Mary Jane. Said she'd go out with anybody. Figgered that was a complement as most women didn't look at me twice.

Anyway, we went to see 'French Connection' together. She hated it. I loved it. We parted ways. Asked my buds to never fix me up again.
 
Been There said:
Wait! You were driving a hearse and going to a Allman Brothers concert, went to a bar, got drunk and fell asleep in back of the hearse only to be awakened by a cop. Now, that's going to be hard to top.
Click to expand...

Yeah... when I first got home, I lived in a 49 Pontiac hearse. Put a Ford van straight axle under it, painted it spray can primer and away we'd go. Actually took it to a dragstrip and burned up the quarter mile in 21 seconds. :ROFLMAO: Got beat by a VW square back. :D
Sadly, the only pictures I have are when I tore the front end out to install the axle. Also, that was before I decked out the inside with heavy purple drapes and walnut paneling and put in a rear heater. (wasn't much need for a heater in the back when I got it). :ROFLMAO: Wish I could re-connect with my buddy Gordon as I remember he had a picture of it at the drag strip.



hearse 5.jpg
 
bobcat48 said:
So I went on a double date with a buddy of mine, we went parking, he was in the front seat with his date, and I in the back seat with mine. After a bit of making out, he says, "Hey, let's do something crazy, let's switch off". So his date climbed in back with me, and mine got in front with him. It was weird and awkward, but crazy things happen. I ended up marrying her after several years. Here's a pic after our son was born.View attachment 290983
Click to expand...
lovely pic @ bobcat 48
 

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