Gwen is depressed: she's been invited by the Mayor to present the Humanitarian of the Year Award, but she's mortified by the prospect of seeing her old acquaintances again and having to explain her poverty and unemployment. Ashley is upset too, worried that his dress won't be ready for the ""tri-state 'Hello Dolly' competition."" Gwen realizes for the first time that Ashley is Guy's son. Terry encourages Gwen to go to the gala anyway and reluctantly agrees to make a new dress for her. Gwen unsuccessfully tries to recruit Danny as her date for the evening, but has to settle for Guy. When Guy arrives to pick her up, Gwen promptly rips her gown in the loft's heavy door.

The resourceful Guy helps do a quick remodeling job on another dress--Ashley's--and Gwen is able to arrive at the gala looking good. At the gala, Gwen's pretentious friends ask about her dress and her date. Gwen says she's wearing a Terry Reynolds original and that Guy is a Spanish count. Guy surprises her by speaking fluent

Guy has found himself a new girlfriend who he proudly shows off to Gwen and Terry. Gwen is relieved that now she won't be the constant target of Guy's aspirations, but surprisingly she misses the attention he gave her and she becomes jealous of the new woman in his life. Also, Danny can't believe his good luck when he hooks up with a songwriter for a project he's working on. Unfortunately, he finds out the man was literally a song writer--he wrote one big hit years ago and hasn't come up with anything else since.

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.

Danny and Terry invite their old friend Mickey, now a firefighter, over for dinner and he and Gwen are instantly attracted to each other. Neither one will admit it, however, and they both go to elaborate lengths to prove their indiference while still running into each other. Danny has an idea for his new newspaper column, using overheard snatches of conversations to provide a colorful, intriguing pastiche. He soon decides, however, that the bar's patrons are the dullest people in the world, so he makes up cocktail napkins with conversation starters on them. His ploy works too well.