liff 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. He ends up with what is an unusual problem for him - two dates - but the predicament he achieved in a typical Cliff manner. After he bribed Carla to go with him, his first choice of a date, Diane, who initially declined his platonic invitation due to a timing conflict, changed her mind and agreed to go with him. Cliff would rather go with "classy" Diane. 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. On a further bribe by Cliff, Carla agrees to the change. Diane with Cliff and Carla with who she coins "tall, dark and gruesome" double date, Diane unaware that Cliff asked Carla, and Carla unaware that Cliff asked Diane first. An unintentional disclosure post-ball leads to a series of events that may make Cliff regret asking either Carla or Diane, or that may still make it the most memorable date he has ever been on in every respect.

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