What is the most memorablely (BAD) date you have ever been on?

McMillanD
What is the most memorablely (BAD) date you have ever been on?
I didn't date much, but even out of the few experiences I had, one was truly memorable for all the wrong reasons.

I had known this guy for years and somehow missed (or made up in my mind) that he was a very different person than who he actually was. On our "date" he spend the night telling me all about his previous conquests... his many many MANY conquests... and topped it off with rating their skill level and attractiveness out of 10 (no joke). I don't know if this was supposed to impress me or if he was intentionally trying to scare me off (no one is that dumb right?).
This was bad enough as it was, however I had gone to high school with this particular guy and knew the majority of the girls he was talking about (it's a very small town). Some of the graphic mental images he gave me of what they had "let him do to them" will forever be stuck in my brain.
I was sitting in the passenger side of his truck for nearly 2 hours thinking how "lucky" (not) I was to finally get the chance to go out with him, especially after crushing on him so hard throughout high-school. It was a real disappointment to say the least. I guess it goes to show how expectations never live up to reality.
Now I am probably on that list, and I wonder if he regales all of his dates with this "show of masculinity" or if I was just super lucky.

Who else has a memorable date for all the wrong reasons?

Perhaps we can learn or laugh from eachothers misfortune.
What is the most memorablely (BAD) date you have ever been on?
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