Weirdest or worst?
Worst date, the girl was a horrible conversationalist, dumb as a brick, and had a laugh like Mr. Ed. It was a blind date, and I would've been far happier if it was a deaf-mute date.
Weirdest? Super Bowl, 2000 (Rams/Titans). It was a double date with me and my buddy and our girlfriends, and we convinced the girls to answer the door for the pizza guy topless. After that my girl told his girl about my "awesome athletic legs", which led to my buddy and me stripping down to our underwear so the two girls could have a hands-on (which predictably ventured north) comparison. This in turn led to a girlfriend-swap of sorts that lasted about two months.
Weirdest...and most awesome.