First, I have to admit that this "worst date" story isn't mine, but I have been granted permission to share it from one of the involved parties. I will try to keep this as polite as possible. If anyone is offended, I'll delete the post, but I had to try putting it up here, because I think it's a pretty good contender for "Worst Date in History".
A good friend of mine, Brad, was engaged to a woman named Janet about six years ago. One afternoon, they decided that, with Brad's roommate Jim out of the apartment, they would spend the day having a drink, a nice lunch, and playing a little scrabble. A few drinks turned into an alarming number of drinks, and soon, Brad and Janet found themselves quit inebriated and lunch was skipped in favour of scrabble. They decided after their game, they were hungry, but that cooking was too much trouble - especially while intoxicated - so they opted to order in.
Brad didn't have a computer at that point, but Jim had graciously offered to let Brad to use his whenever he needed to. Brad went into Jim's room to use his computer to order pizza, and Janet followed, and sat on Jim's bed. It must be noted here that Janet was not yet dressed, and was wearing nothing. This becomes important very shortly.
As Brad was perusing the website of the local pizza joint, he heard Janet say, "Uh oh!" and start to giggle. He replied, "What to you mean, 'uh oh'?" Janet replied with more giggles, and then, "I pooed". Janet was so drunk, she'd lost control of her bodily functions, and had defecated on herself, and - potentially - Jim's bed. Brad proceeded to panic, hauled Janet into the bathroom, placed her in the tub and hosed her down. Upon close inspection, he discovered that Jim's bed had not been damaged, but he frantically washed and Fabreezed everything.
A few weeks later, Janet emailed Brad and ended their engagement and their relationship, claiming that she needed to find herself. Good riddance. The incident, which became known as "The Poo Story" circulated among our friends, was retold on podcasts and in blogs, and became the stuff of legend - to everyone but Jim. Brad firmly believed that if anything could end his fifteen years of friendship with Jim, this would do it.
About a year ago, Jim and Brad were sitting in their living room sharing a few beers, and Brad decided it was time to confess. He told Jim the whole story. Jim sat quietly, absorbing the whole tale, and then took a swig of his beer before replying, "That girl was a giant slice of crazy pie. Stop dating insane women."
Happily, Brad is now dating a lovely, sane woman, and is drinking substantially less. Jim purchased a new bed.