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Where was the worst date you've ever experienced?

My first boyfriend was a bad boy and a daredevil and riding on the back of his motorcycle was NOT a pleasant experience. He thought it was funny.
 
There was another one that was the worst and the best at the same time.

We were in a large theatre up in the balcony area watching a movie and my date (who was hot as fuck) started to make out with me and he pulled my pants down and took his off and sat on my cock.

The usher came by and he just pretended he was talking to me but I was freaking out. I think he saw what we were doing but probably didn't know how to handle it.
 
When I was a senior in college, although I already had a girlfriend, there was another girl who was constantly coming onto me, very often quite physically and publicly, although I never reciprocated or gave her the slightest indication that I might want a relationship with her or even a friendship. On one school holiday, when we were both at our respective parents' houses for the break, I ran into her and, thinking, what the hell, she's an easy lay, we'll go out to dinner and afterwards return to my parents' house and fuck--my parents being on holiday themselves. So we have dinner, return to the house, I put on Mozart's Clarinet Concerto in A and I take her to bed. Everything's going really well, I'm enjoying myself and so is she when, just when I'm halfway inside her she says, "Do you love me?" I hesitate, she bursts into tears, I lose my erection, and she spends the next hour alternately asking why boys always seem to want to just fuck her and telling me it doesn't matter she wants me anyway. I never managed to get hard again, she shed more tears, and...well, you get the idea. All of this time Mozart was on repeat, and so--unfortunately and amusingly--every time I hear the Mozart I think of that evening and her. Also, unfortunately and amusingly, with no encouragement on my part, she still wants to be in my (and now my partner's) life decades later, calling a couple of times a year and suggesting 3-ways. Definitely my worst date.

 
^
I neglected to mention that she's now a widow--a somewhat merry one, actually--her second husband having committed suicide.
 
Where?

On a frozen lake.

I've never done traditional dating- dressing up for a scheduled meal, or show, or dancing/clubbing, . . . anything like that. It's just not me.

It wasn't until the third time out ice fishing with the guy that I realized he was freezing cold and miserable doing whatever he had to do to try to woo me, and that he thought of our fishing adventures as dates.




Maybe your next thread should be; What's the most miserable/uncomfortable thing you've done to try to win someone's affection. :)
 
cabinfever said:
There was another one that was the worst and the best at the same time.

We were in a large theatre up in the balcony area watching a movie and my date (who was hot as fuck) started to make out with me and he pulled my pants down and took his off and sat on my cock.

The usher came by and he just pretended he was talking to me but I was freaking out. I think he saw what we were doing but probably didn't know how to handle it.
Click to expand...


The usher may have been excited by it.

He may be telling stories to this day about the time he caught this gay couple fucking in the balcony and he talked to one of them, who chatted like it was nothing.
 
Latimer said:
I neglected to mention that she's now a widow--a somewhat merry one, actually--her second husband having committed suicide.
Click to expand...


Yikes!


just when I'm halfway inside her she says, "Do you love me?" I hesitate, she bursts into tears, I lose my erection, and she spends the next hour alternately asking why boys always seem to want to just fuck her
Click to expand...


I wonder if anyone ever explained to her that, if that's the way she felt, she should be getting the "I love you" before she fucks ...

(There are so many people who need that explained to them ...)
 
LoveMyPeppermill said:
The usher may have been excited by it.

He may be telling stories to this day about the time he caught this gay couple fucking in the balcony and he talked to one of them, who chatted like it was nothing.
Click to expand...
Never thought about that possibility until now and you may be right.

I was sure were going to be arrested or at least be escorted out of the theater.
 
When I was 19 I had my first date with an "older" man. He was probably like 25. As soon as he picked me up it became clear that this was less of a date than it was a hookup.
We tried messing around in his car but it was too small and there was nowhere to park that seemed safe enough, so we ended up at a park, on a picnic table, despite the fact that no one was allowed in the park after dark.
I think we were sixty-nining when we were suddenly bathed in the light of a cop's flashlight. He wanted to know what we were doing, despite it being obvious. He kept asking until my friend said "Just what you think . .". The cop seemed embarrassed and let us go. When we got back in the guy's car I said "I need a drink!" so we went to a liquor store and he bought a six pack. This was the early 80's when it was still cool to drink Michelob.
After my second beer I had to piss so I went around to the side of the liquor store to relieve myself. When I got back, his car was gone.

The worst, however, was meeting this guy at a bar when we were both really drunk. We made plans for later that week but something happened - I don't remember what - and had to postpone it a week or so. In the interim we talked on the phone just about every day. I liked him. He was sweet, a little effeminate, and had terrible self-esteem.
At the time I was still living with my ex (never do this!!!) and we were constantly trying to make each other jealous. He was super jealous of my date with this guy so he arranged a date himself with this guy Joe I had been crushing on for a long while. I was horrified, but glad I had the date that day.
We didn't make any plans. I was going to go to his apartment and we'd take it from there. When I arrived, he seemed disappointed and aloof, as was I, because he didn't have the same appeal he did in low light and with a lot of alcohol in my veins.
It was pouring rain so we decided to just hang out that afternoon. I had brought a movie to watch, just in case. I don't remember what it was but it was a funny one, at least I thought so, but he didn't even crack a smile once. I wanted to just go, but there was no place for me to go and I didn't want to go home where my ex was hanging out with Joe. So I stayed. We ordered a pizza. Watched some TV. Sat in uncomfortable silence for a while. I knew this guy was wishing I would leave, but while the date was horrible, it was preferable to me going home and seeing my ex with Joe. I think I stayed until eight o'clock or so. When I got home I thought the apartment was empty until I heard the sounds of sex in my ex's room. I took a shower and went to bed. I was miserable. Worse, Joe stayed over that night. :mad: Just awful.
 
I've mentioned this here on JUB before, I'd been running into and chatting with this guy for a month or so, I met him through mutual friends. This night we went out to dinner and it was good ect apart from the fact that he said he had a bit of a headache so I offered to cancel the rest of the date for another time. He didn't want that and so we ended up going back too his place and got hot and heavy on the couch for a while then ended up in bed, me on my back him riding me, we were really going for it when all of a sudden he went as white as a sheet and next thing I knew he was vomiting and shitting all over me ( I kid you not) I grabbed him by the sides and lifted him off and threw him away from me and I stormed into his bathroom and run the shower and tore the condom off and scrubbed myself raw until the water run cold. When I came out into the bedroom he was still curled up on the floor moaning and groaning and I got the gilts and helped him into the shower and got him cleaned up apologizing all the time for using all the hot water. I got him cleaned up, put him in boxers and t-shirt stripped and remade his bed and got him settled in it and then after talking realized that the poor guy had been struck with food poisoning from what he'd eaten for lunch earlier in the day. I sat there on the bed with him until he fell asleep and found a large bowl in his kitchen and put that beside him and a glass of water on his nightstand and got out of there. I ran into him a month later and we just hugged and laughed and left it there, we laugh about it now, but still it has been the worst (shittiest) date I've ever been on so far.
 
I can't remember a lot of dates. They were more like hook-ups, so wining and dining wasn't an expected part of the evening.
 
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