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

I've told it before but to shorten the story, he was so offensive I dumped my glass of ice tea in his lap.

I met another guy for breakfast only to learn that his wife had only been dead for four days.

Then there was the guy who I met for a bike ride. He dumped me on the bike trail and was loaded up and gone by the time I caught up.

There were some awkward ones, all righty.....
 
MANY years ago, before things like cross dressing or being trans was more in the open, I had a FIRST date with a man who talked about how he liked to wear womens clothes, and go out in public. I am much more comfortable with such conversations now...but not upon a first meeting with someone
 

Maybe 15 years ago, I accepted a dinner date with a man who I'd met before
at a community event, funny and kind he was. We had chatted about all sorts
of things at the event.

At dinner, he says "I want you to know I am happily married, but I do hope
we can go out again sometime, I hope you say yes"

Me: married I replied? No future dates...I did not want to hear further about
why he was married and dates. Then he said "may I give you a kiss before you
leave the table, I can see that you are not pleased I am married"

He did not get the kiss...

so a bit awkward but I have several that were far more awkward than this one lol
 
Last edited:
jujube said:
I've told it before but to shorten the story, he was so offensive I dumped my glass of ice tea in his lap.

I met another guy for breakfast only to learn that his wife had only been dead for four days.

Then there was the guy who I met for a bike ride. He dumped me on the bike trail and was loaded up and gone by the time I caught up.

There were some awkward ones, all righty.....
Click to expand...
LOL - "Dumped ice tea in his lap."
I've heard of a cold shoulder, but............
 
Marie5656 said:
MANY years ago, before things like cross dressing or being trans was more in the open, I had a FIRST date with a man who talked about how he liked to wear womens clothes, and go out in public. I am much more comfortable with such conversations now...but not upon a first meeting with someone
Click to expand...
@Marie, I wouldn't even have let him finish the sentence. I would have been GONE!
 
In my mid 20s, someone wanted me to go on a blind date with her friend. I wasn't that interested and when I got there the woman apparently lived in a motel room? After introducing myself and going inside, she said "I'm not sure if I really want to meet someone" and appeared to have an ornery disposition.

I turned around, walked straight out to my car, drove off and didn't look back.
 
Bad memory here. :cry: I'd known him from school but not to the point of ever having had a conversation... but he called and asked me out, and I accepted. Drove to an abandoned quarry which made me nervous right away... but I was naive and... well, I was. Anyhow, we just sat there talking for a while and I relaxed because it was a good normal conversation.

Then his voice changed and he sounded weird. He became very unfocused and wasn't making sense. He reached for the glove compartment and I envisioned a gun and being shot/abandoned in an old quarry. But there wasn't a gun in there... he had brochures of how different species in the animal kingdom mate and started telling me that every living thing "does it." Good gracious.

Thankfully a firm "put those away and take me home because we are NOT going to be doing it" worked. Two years or so later after I'd moved out of town, my mama told me that he'd died of a brain tumor. I always wondered (still do) if that had something to do with his bizarre change in behavior/voice that night.
 
jujube said:
I've told it before but to shorten the story, he was so offensive I dumped my glass of ice tea in his lap.
I met another guy for breakfast only to learn that his wife had only been dead for four days.
Then there was the guy who I met for a bike ride. He dumped me on the bike trail and was loaded up and gone by the time I caught up.
Click to expand...
Those are awkward alright, @jujube ... that second one could have used some ice dumped on him, too. 😦
 
Something more funny than awkward ....
. on my very first dating experience, as a 13 yr. old in Jr. High, I was invited to a movie night with a boy in my class.
His father drove us.

Well, apparently his mother wanted to make sure nothing happened between us ... lol ... Whatever he had eaten for dinner that night must have been soaked in GARLIC ..... sitting next to him in the movie theater was just awful. I kept my distance the best I could, and couldn't wait to get home and away from the SMELL. He was history!

I wonder how long his mother kept sabotaging his love life, or if he ever caught on? 😄
 
JustBonee said:
Something more funny than awkward ....
. on my very first dating experience, as a 13 yr. old in Jr. High, I was invited to a movie night with a boy in my class.
His father drove us.

Well, apparently his mother wanted to make sure nothing happened between us ... lol ... Whatever he had eaten for dinner that night must have been soaked in GARLIC ..... sitting next to him in the movie theater was just awful. I kept my distance the best I could, and couldn't wait to get home and away from the SMELL. He was history!

I wonder how long his mother kept sabotaging his love life, or if he ever caught on? 😄
Click to expand...
My first date: a rancher's son asked me to dinner with his parents.
I complimented his Mother on the chicken.
I was age 13. She said, "It's not chicken, it's rabbit."
Me: "You mean a cute, little bunny rabbit?"
She said they shot him in the pasture. I started crying. I couldn't eat.
That's the last time they invited me.

I feel bad now for his Mother, who prepared a nice meal.
 
Last edited:
A fellow officer I dated in the Air Force drove all around an area of Texas I was uncomfortable with, and we argued about it, so he kicked me out of the car and drove off. I found myself in the middle of an oil field out in the boonies. Thankfully, their security saw me and drove me back to base. Not the end of the story, but the end of a budding romance.
 
When I was 30 & recently divorced, a co-worker suggested I sign up with a singles dating service. They gave me a phone number.
The woman was an elementary school teacher. She lived in an apartment rent free because her father owned the building.
We went out to dinner in a ritzy part of town (Rodeo Drive). She suggested it because she liked to window shop. While we were chatting, a Bentley parked in front of the restaurant & I noticed my date staring at it & she looked almost hypnotized.
I said, "Nice car, eh?"
She said, "Yes, & the man I get involved with has to be able to buy me a car like that or I wouldn't waste my time with him."
I thought she was joking, so I laughed.
She said, "What's so funny; I'm serious."
I said, "Well, we all have our priorities.....whatever........"
When I took her back to her apartment, she invited me in. I had a great time with her cat - much better than my time with her. :giggle:
 
Alligatorob said:
My first dozen or so dates were all pretty awkward...
Click to expand...
Mine too, although not really awkward, just difficult. When I was seventeen I met a new dance partner who was just thirteen, we clicked, as platonic friends that is. We danced Latin & Ballroom, it meant lots of training and travelling. We just grew together, were meant for one another. Five years later, we married and this year we will celebrate our fifty-fifth wedding anniversary.
 
I was downtown shopping and walked out of a store when a guy was walking in. He came to a halt and said, "I know you. I always see you in the hall after my English Lit class." I said, "You look familiar, but I know we haven't met." He said, "My name's Frank," and stuck out his hand. I shook it and said, "My name's Bella." We talked for a few minutes, and then he asked me for my number and said he'd like to meet me for a drink. I said OK and gave him my number. He called me that night, and I met him two nights later at a local place downtown.

When I walked in, he immediately said he wanted to go to a nicer place along the river. I was wondering why we just didn't meet there to begin with, and he said he just thought of it. I said, "Alright." As I was walking to my car, he said, "Why don't we ride over together?" Again, I said, "OK." That was my first mistake. I should've never agreed to go to a second location with someone I really didn't know. We got into his car and took a fifteen-minute ride to a restaurant/inn. We sat at the bar, or, I should say, I sat at the bar while he stood next to me with his arm around my chair. He was a little close for comfort, so I said, "Why don't you have a seat?" He said, "No, I'm fine." He was making me uncomfortable by insisting on standing so close. I thought it was strange. After a few more minutes, I said, "Please, sit down." He finally did, but pulled his stool right up against mine. We had a drink and talked, then he wanted to go someplace else. Again, I thought it was odd, but I told myself that maybe he just likes to bar hop. That was my second mistake.

We got into his car and started driving back into town, as he was driving, he put his hand on my thigh. I immediately asked him to please not do that. He seemed a little offended but took his hand away... for a minute, and then it was right back on my thigh again. I said, "Please don't do that because we really don't know each other and you're making me uncomfortable." Then he snapped. He said, "You won't let me do that, but you'll let some n*gger fu@k you two days from now!" I knew I was in trouble. He kept on yelling obscenities at me. We were downtown by now. When he stopped at a traffic light, I jumped out of the car, slammed the door, and told him to find someone else to insult. He followed me in his car, shouting out the window for me to get back in the car.

The first phone booth I found was out of service. I ran down the street to a gas station and saw another phone booth. I dialed my parents' number, and my mom answered the phone. I didn't tell her why I was calling, I just asked to speak to my dad. At this point, Frank pulled into the gas station and got out of the car. I was speaking to my dad and told him what was happening, where I was, and asked him to please come and get me. I was lucky he was at home because he was often at his club in the evenings. When I saw Frank coming, I pushed my back up against the phone booth door and propped my feet up against the opposite wall so he couldn't get the door opened. He was pounding on the door and shouting. I didn't know if I could hold out until my dad got there. I was pushing with all my might. All I could think about was keeping him out of that booth.

My parents lived about ten minutes away from where I was. I don't know how my dad got there so fast, but he was like lightning. When he pulled into the gas station, I was so relieved. He jumped out of his car and approached Frank, saying, "What do you think you're doing? Back off. That's my daughter! Get over here." Frank was visibly shaken and began telling my father a bunch of nonsense. My dad shut him down. He pulled out his badge and told Frank he wanted to see his driver's license and vehicle registration. Then he told him he had violations on his vehicle and that they were illegal. He told him he had ten days to get them fixed. Then he told him if he ever came near me again, he'd put him in a full body cast. That was the last I ever heard from Frank. Thank you, dad. You're my hero.

I can't leave it there because you'll want to know what my dad had to say to me, right? When we got into his car, he asked me what happened. I told him the truth and said that I'd made a big mistake. I should've never left the first location or my car. He asked me if there had been any funny business that led this guy to believe that I was interested. I said, "Are you nuts! You know me better than that." He said he had to ask. OK, Daddy, you got your answer, no funny business. None. I thanked him profusely as he drove me to my car. I asked him what he was going to tell my mom. He said, "What do you want me to tell her?" I said, "How about that I had car trouble?" and that's what we agreed on. I wasn't in the habit of keeping things from my mom, but I thought it best in this instance because she would've been very upset.

And that, my friends, is the story of my worst date. :oops:

Bella ✌️
 
I invited a young lady to a Van Morrison concert. I had some car problems that night and I had to have my older brother drive us there and pick us up. She was not happy.

After seeing the concert she decided she didn't like Van Morrison. She was not happy.

It was cold waiting for my brother to pick us up. She was not happy.

I tried to put my arm around her. She was not happy.

I offered her my coat and she refused.

So on the way home she sat in the back all by herself. When we got to her place my brother pulled up and shut the motor off expecting me to walk her to the door (be a gentleman - kiss good-night, ya know?). Nope - she got out and I had him drive off.

I don't think she was happy. Guess it was my fault.
 
Another one:
After just divorcing my cruel, dominating first husband, the last kind of man I wanted was
the same. This man kept asking me out, saying he wanted to take me out to a nice steak dinner.
Turned him down twice. I had two children at home to take care of. Didn't even want to date yet.
Finally I said, "OK, I'll meet you at the restaurant." (Maybe I'm misjudging him)

He ordered for me. (all right, I guess) but I wasn't yet myself. I'd been beaten down for years.
He told me after dinner we were going to his beach house, spending the night together in front of his fireplace.
First date! I didn't even KNOW the guy! He told me in the morning we would go skinny dipping in
the ocean.

I said, "No, I appreciate this wonderful dinner but I'm going home after dinner to be with my kids.
I will be at work at 7 AM. tomorrow. I'd really like to take things slow, if that's all right."
He reached his hand in the air and snapped his fingers, yelling, "Girl, Girl!" to the waitress.
She rushed over, and he said, "Separate checks here, girl!"

I kept thinking, "Boy, I can REALLY PICK EM!"
 
You must log in or register to reply here.

Back
Top