 Cliff has been awarded Postman of the Year by his branch office - one of 267 awards given out in the Greater Boston area - and wants to have a woman on his arms at the Gala Postman s Ball. That is no easy task. He first asks Diane, with the caveat "no strings attached". Diane, who is touched by the request, has to decline his offer since she already has a previous engagement that evening: her cheese club meeting. Desperate, Cliff next asks Carla - "bribes" would be a better term, bribes with not having to dance, a dress, a corsage, $100 and a VCR. After Cliff sheds a tear, Carla accepts with the bribes. Sam however talks Diane into accepting Cliff s offer and she does agree to go with him after Carla has already accepted. Cliff would rather go with "classy" Diane, and although the guys think he should go with Carla only because she said yes first and the fact that Carla would kill him if she found out he asked Diane first, Cliff makes up a story to Carla that someone else has expressed interest in going out with her instead, a Robert Redford type who drives a Porsche. Carla is suspicious, but agrees to the change with the extra bribe of a big screen TV. Lucas  similarity to Robert Redford is only that the two are both men, but Carla gets along with "tall, dark and gruesome" as she refers to him regardless. The four double date, Diane and Carla unaware of the fact that Cliff asked both. They all have a good time at the ball. But afterward, when it looks like Carla and Lucas will make it to bed that evening, Cliff accidentally lets it slip to Carla that he made the wrong choice in picking Diane. Carla exacts a little revenge by telling Cliff that Diane really wants more from him, specifically that she would like him to run his hands up her arm, while singing Misty in her ear. Cliff is excited. He takes it one step further by pretending to run out of gas in the middle of nowhere. When Cliff starts his hands up her arm and his rendition of Misty, Diane is furious. She kicks him out of the car, and leaves him stranded there. This ends the best date that Cliff probably had in his life.