It's one of the hoariest cliché's in the overtly thick Rom/Com Cliché' Manual: The couple, who will eventually fall madly in love and be deliriously happy by the closing credits, absolutely, positively despise each other when they first meet. And woe betide the first time they spend alone (which for purposes of this exercise we will refer loosely to as a "date"). Everything goes wrong, something dark colored is spilled on someone's white dress, someone's pants catch on fire, and both people stalk away from one another determined to never again go on set ups from their friends.

Still, there are some films outside that particularly painful genre that use horrific first dates to an altogether different purpose. It can be accomplished, in other words, it just has to be done with a modicum of wit and creativity. For our list purposes, we'll keep a somewhat loose definition of "date" to include not just formal goings-out, but also extended first encounters. For your grace in allowing us this liberty, we promise not to include When Harry Met Sally and any films with Freddie Prinze Jr., deal?

Fast Times at Ridgemont High

Participants: High School innocent Stacy (Jennifer Jason Leigh) hooks up with creepy, older dude Ron (D.W. Brown).

Circumstances: Stacy just wants to find out the deal with men, and is just getting used to the idea that she could be attractive to them. Creepy older guy wants to crush some adolescent poon.
What Makes It Awful? Besides the above description? How about they consummate their mutual interests in the abandoned dugout of the high school baseball team. Can you imagine the amount of chew spittle on that cement floor? Not only does it look incredibly awkward, this is actually Stacy's first time, which would seem less than romantically memorable.

Outcome: Between this unfortunate encounter and her subsequent awkward hooking up with fellow high schooler Mike Damone (Robert Romanus), Stacy learns that these boys are pretty much total chumps and determines that she is interested in meeting someone with whom she actually has a connection.