- The gang goes on dates through a service and meet up at the Club Car to tell their odd stories.
- Brain, Helen, Joe and Lowell all agree to give a new Nantucket dating service a try. They also come up with a bet that all contribute to a pot, and whomever has the worst date gets the money. Helen gets set up with Jeffery #16, a waiter that she has to help serve tables with. Lowell meets Monica #187 and though he spends most of the date trying to impress her with hijinks, she likes him enough (and he her) to have a second date. Then Joe shares his plight with Sharon #325, a ventriloquist with a sassy woman puppet that keeps hitting on him. Finally Brian comes in all wet, his date Barbara #242 was a commodities trader and got Brain locked in a phone booth filling with water. They all agree Brian should win and as they leave we see Monica talking with Barbara about their dates, and Jeffery serving Sharon while her purse talks (ventriloquism).
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