Joy and Eddie are in the kitchen waiting for Eddie's friend Webby to come to visit. Eddie describes Webby as the kind of unmarried guy who bartends at resorts and is a ski teacher. Webby arrives and he and Eddie go into a routine of calling each other nicknames before Joy stops them by telling them they are in their 40's. Later, they are at the dining table and Webby is telling Eddie and Joy about one of his adventures in Buffalo where he won an entire bar in a bet. Joy compliments Webby on his charming tales before Webby gets a call to go to an underground Cuban cigar party. After he leaves, Joy says that Webby seems lonely and unhappy, but Eddie thinks that he really is happy. Eddie thinks she said that because she thinks a man can't be happy outside of marriage. Joy decides to hook Webby up with one of her friends - Denise. Over Eddie's protestations, Joy called Denise and tries to set up the date.
At the Woodcock's, Jeff is in bed when Steph shows him her new garish blouse. He says it's cute. She says that's what he says when he doesn't like something. He fesses up and says he thinks the dress is ugly.
Back at Joy and Eddie's, Joy comes home with Denise to find Eddie and Webby playing video games. Webby is interested in Denise and likewise. Webby invites Denise to a Yankees game; unfortunately, Eddie was supposed to go to that game with Webby. Days later, Joy tells Eddie that Webby is dating Denise and that he evens has his stuff at her house. Joy calls Denise's house to prove that Webby is in a relationship and invites Denise and Webby to dinner with them and the Woodcocks.
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