Hapless, jobless Steve Summer is infatuated with Terry, who for some reason has always had a tough time breaking up with guys, and Steve is no exception. She implores Gwen to talk to Steve, her old high school boyfriend and let him down easy. But Steve doesn't comprehend Gwen's message and thinks he can win Terry's heart a different way: by learning to dance.

Also, Danny and Guy find a thousand dollars in cash in the bar. When an owner doesn't claim it in two weeks, they figure by rights the money is theirs. They spend in on scaplped Knicks tickets, but when they try to buy another pair, they come up short of cash so they throw in a watch from the lost-and-found box to pay off the scalper. Promptly after doing this a minister arrives looking for his heirloom watch and a old woman shows up looking for her thousand dollars.

Gwen and Terry are trying to get insured, but the agent tells them they are not qualified. When he mentions that same-sex domestic partners are eligible for his company's insurance, Gwen says that's exactly what she and Terry are, and surprises Terry with a demonstation of her affection. The agent is not entirely convinced about this, so he plans to make a visit to them at home to check out their living arrangement, leaving the two women to try and set up a convincing domestic household in time. Also, Guy is challenged for the title of ""Mr. New York,"" the businessman who best knows where to go and how to get things done in the city.

Mrs. Francis is involved in a school charity auction, and Gwen convinces Tery and Danny to participate, despite their better judgment. Danny warms to the idea, though, when he meets one of the women who might be bidding on a date with him. But he's sold to his mother Tina, who's mad about him missing his lunch dates with her. Danny's agent Scott lowers the bidding on Terry by spreading rumors about her health and mob connections, then buys her for himself. Guy shows up prepared to spend big money to at last get a date with Gwen, but a former classmate of hers puts up $25,000 to create the fantasy prom he never had with her. Gwen also gets reacquainted that night with Steve, another former high-school classmate whose ego has fallen on some hard times since graduation.

Gwen wants to give down-and-out Steve a break and let him have a job with their small business. Terry agrees because it will give her an opportunity to show Gwen what a good boss should be like. But Steve would try the patience of Job as he mangles up the most simple tasks assigned him and is costing them a lot of money. Meanwhile Danny is trying to write a profile of Guy, but he can't penetrate the wall of secrecy surrounding Guy's past, and the clues he does come up with suggest all sorts of exotic and unbelievable things.

It loooks like Gwen's sacred ""no sex before the fifth date"" rule may cause some real trouble, because the spontaneous route may be the only way Mickey will be able to participate--before or after date no. 5. Guy decides to hold a literary competion to help nuture a Bohemian atmosphere at the bar, but the main result is a pair of competing, revealing memoirs written by Terry and Danny.