Not so much the crappiest, but the weirdest by far.
I was 16. It was during the summer. A good friend and I used to go into a neighboring town and hang out on "the drag". Well, I was the prototypical dork - thick glasses, beater car, played w/ computers, D&D, etc. etc.

Anyway, my buddy was definitely the ladies man. One night he met this pretty cute girl. Problem was, she was there with her anything-but-cute-or-even-remotely-easy-to-look-at cousin.

Well, he asked me to be cool to her to help his chances with the cutie. Of course, I complied.
Now, I never touched the girl. We were alone together one time -
one time! - and that was to make a McDonald's run one night. She tried to get kinda close while we were driving out there, but I was having none of it. When I could sense her prepping to make some kind of move, I'd conveniently see someone I knew going the other way and wave or yell at them (of course, I was making this all up to throw her off).
Fast-forward a couple days. The cute girl has been over to my friend's house a couple times (I almost lived there, so I was always over). Of course, anything-but-cute-or-even-remotely-easy-to-look-at girl always came with her.

We also find out both girls are related to a pretty good friend we both went to school with and they're staying at his place. More attempts to stay in a public environment with anything-but-cute-or-even-remotely-easy-to-look-at girl and not let her get me alone. I'm thinking my buddy owes me super-big-time.
Move forward about a week. Anything-but-cute-or-even-remotely-easy-to-look-at girl finally gets the hint. Unfortunately for my buddy, she takes cute girl with her. We haven't seen them for a couple days. My life is immediately better. One day I borrow another friend's motorcycle and cruise around town for a few. I happen to be going down the road where the girls are staying (there weren't a lot of roads to choose from). I see their relative "Rusty" outside. He waves me down. I pull over, but am still on the bike and it's running.
Rusty is about the same size as I am. He has a reputation for being a nasty guy, but I've never had any problems with him.
He walks up non-chalantly and asks me what's up. Of course, the typical teenager conversation ensues. Well, out of nowhere he asks me if I banged his cousin

Of course not!! I never even touched her! Well, she told him I hit it and quit it and he feels the need to beat me down (I just then noticed she was standing outside the front door). Grrreeeaaaatttttt......
He takes a swing at my face. I duck it and launch the [censored] outta the bike to get outta dodge. Luckily, it was a 750 cruiser and had decent pick-up. I'm gone.
I get the bike back to the owner. Tell him of my amazing escape. In a turn of events I'll never be able to repay him for he decides to get all pissy 'cause "it could've damaged his bike"

and wants to go see Rusty.
We hop in his pickup and go pay Rusty a visit. Turns out, when Rusty has real opposition he isn't quite the guy we all thought he was. He did nothing but back down and apologize

Darrel and the Dorks: 1
Rusty the biyatch!: 0