Maya's enrollment in a photography class causes problems on multiple levels between her and Elliott. Elliott takes an immediate dislike to Maya's teacher, Martin Spancer, when he insults Elliott's work for being too commercial. Then when he assigns Maya to do a nude self-portrait, Elliott claims that he only gave her the assignment so that he could see her naked body. Believing that Elliott's accusation is based on his personal dislike for Spancer, she disregards him. However, when Spancer raves about her nude photos and invites her to go away with him for a special weekend session, Elliott becomes even more convinced that his intentions are purely sexual. Meanwhile, Finch becomes extremely jealous when Nina's new assistant Brad begins entertaining Jack with magic tricks.

After yet another relationship goes sour, Nina realizes that her lack of romantic success is probably due to her tendency to make bad choices in men. Her resolve to start making good choices is tested almost immediately when her old boyfriend Roy breaks out of prison and she falls in love with and begins dating not only Roy, but also the cop who is pursuing him. Meanwhile, Jack, Finch, and Elliott engage in a series of wagers on how predictable each other's behavior is.

A planned Blush article on lost loves leads everyone to reminisce about their own lost loves. The saddest story belongs to Elliott, who saw his dream girl sail out of his life when a hit and run driver knocked him down on his way to propose to her. The story has an extra meaning for another person, however. When Elliott describes the incident, Nina realizes that she was the driver in question. Meanwhile, Finch wants desperately to convince the world that he is actually married to Adrienne, so to help him out, Jack takes out a big wedding announcement in the New York Post. Unfortunately, the attention it draws is of the unwelcome variety: an INS agent arrives at the office charging that the marriage is a sham. And why does it matter what the INS thinks? Because it turns out that Adrienne is actually a Canadian citizen whose work visa has just expired.