Ep 24. The Odd Couple (1)

As Nina is consoling supermodel Adrienne Barker, Finch is surprised when an old high school rival drops by the office. Now a wildly successful grocer, Barry presses Finch about his career. While trying to inflate his position at the magazine, Finch accepts an invitation to join Barry and his fiancée for dinner. Meanwhile, in an effort to make an impression for a magazine article about art in the executive suite, Jack sends Elliott out to buy a suitable painting. But when he's unhappy with Elliott's choice, Jack buys one on his own, oblivious to its sexually charged subject matter. In hopes of impressing Barry, Finch sees that Adrienne is vulnerable after being dumped by her boyfriend and talks her into being his dinner date. But when Barry and his fiancée arrive, Finch sends them packing when Adrienne asks him to join her for a bath instead. And after Barry discovers why, he's more than a little jealous of Finch's good fortune. Meanwhile, when Jack insists on being photographed with his pornographic painting, neither Maya nor Elliott can talk him out of it. So only after the photographers arrive to take pictures does Jack learn of the problem. Following his evening with Adrienne, Finch couldn't be happier. But when she suggests putting off their next date, Finch worries that he's being dropped. Once her ex-boyfriend sends flowers in an effort to make up, Finch intercepts the bouquet and claims they are from him. And after realizing that the only way he'll be able to hold onto Adrienne is to lower her self-esteem, Finch fuels the notion that she's getting too fat to work as a model and then proposes marriage -- which Adrienne accepts!