It all starts out innocently. In order to help Elliott get a great deal on an apartment, Maya agrees to pose with him as a married couple. To complete the charade, the two are forced to kiss. This development is harmless enough- until they find themselves kissing again voluntarily. Awkward could hardly begin to describe relations between them afterward. They work through the awkwardness, but by the end, both Maya and Elliott realize that the long, bumpy road, wherever it may lead, is just beginning for them. Meanwhile, when Jack discovers Finch has been renting out his parking space, it leads the two into a battle over trust.

Maya and Finch attend designer Oscar Milos's fashion show using Nina's tickets. At the party, a drunken Maya makes some caustic remarks to a newspaper reporter, resulting in Milos pulling $3 million worth of advertising from the magazine. Maya decides to try and get the advertising back herself, without help. Meanwhile, Jack helps Elliott with his new girlfriend. Jack sends Elliott's date poems, flowers and much more in Elliott's name. She ends up dumping Elliott because ""he"" was smothering her.

Finch is very frustrated when an old nemesis, Barry, shows up one day to gloat over his success. Not only does Barry own a successful business, but he is also engaged to their high school homecoming queen. Finch agrees to a double date with Barry and his fiancée, and he wants desperately to show Barry up by scoring a better looking date. He finds his answer in the form of Adrienne, a gorgeous supermodel. Adrienne would normally be way out of Finch's league, but by manipulating her many insecurities, he makes her fall for him. However, he still has one more obstacle to overcome-Adrienne's ex-boyfriend has decided he wants her back. Finch is forced to take desperate action if he wants to hold on to her, and does-he asks Adrienne to marry him, and surprisingly enough, she says yes. Meanwhile, Jack makes plans to have his photo taken in front of a new painting in his office, but unfortunately, he doesn't realize that the painting depicts an obscene act.