 Woody confesses to the gang that he has a thing for Rebecca after she mentions that she thinks he s cute. This sparks a bet among the gang at the bar that he can get a kiss from Rebecca before midnight. The bet is extended to Sam, when he says he has a better chance with Rebecca than Woody. So the bet becomes who can get a kiss from her before midnight first. Rather than getting an honest passionate kiss, each resorts to trickery to try and get the lip lock with Rebecca. Sam first feigns a heart attack that requires mouth to mouth, then Woody pretends to need a reading partner for a romantic scene in a play (Woody almost gets the kiss except he loses track of his goal and is sidetracked). Sam follows this with a morality play with an old girlfriend, Woody then tries to hypnotize Rebecca, then Sam pretends be sent to war after enlisting. Rebecca, who clues onto the fact that both Sam and Woody are trying to kiss her, bribes Carla into telling her the reason. After finding out, Rebecca aims to get back at the two of them. Without telling the other, Rebecca tells each of them that she knows about the bet and wants him to win the bet. To make it look natural, she sets up a rendezvous with Sam in her office while she s pretending to be asleep on the couch. Apparently she tells Woody a similar story with one twist: he is to be the one asleep on the couch. In the darkened office, this leads to the kiss happening between Sam and Woody, the kiss which is witnessed by everyone. After being mad at each other for being caught in the compromising position, they, as friends, make up. As such, Woody ends up asking Sam a question that only a real friend can ask.