I did have one "disaster date" in high school. Finally got up the nerve to ask a cheerleader out to a carnival and to my astonishment she agreed. When we got to the carnival, I discovered that I'd gotten the dates wrong - it didn't open for another couple of days. Oops #1.
In desperation I suggesting horseback riding, as I knew of a stables a couple of miles up the road. Turns out she's an avid rider and wants to go back home to change. Okay. She comes out looking like a British houndswoman, complete with riding boots, pants, jacket and the little whip thingy. I hadn't been on a horse since I was ten.
We get to the stables, turn the corner of the driveway, and the stables has burned to the ground, apparently about a year before. Oops #2.
I gave up. How about bowling? She did that, wearing the riding gear.
I never had the nerve to ask her out again.