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.

Finch announces the engagement at the office, but it takes several minutes to make everyone believe it. When they finally do, though, it begins a heated argument between Maya and Elliott over whether Finch's and Adrienne's love is for real. It may not matter either way, though, because once the news of the engagement spreads, Adrienne's ex-boyfriend Brian shows up at Blush with plans to beat up Finch. Finch manages to avoid Brian temporarily, but the incident forces him to speed things up yet again-with a wedding that very day. Finch and Adrienne are married after Brian punches Finch. But...Elliott and Maya are also married while looking for Finch in a mass wedding.

Finch and Adrienne return from a wonderful honeymoon in Tahiti, but upon their return, Finch is hit with a hard dose of reality. If he is to maintain his ""cool"" image in Adrienne's eyes, he will have to give up a lot of his favorite things, such as action figures, sci-fi conventions, and cat shows. What makes this so problematic is that his cat Spartacus has just made the finals of a big cat show, and winning has been a lifelong dream of his. Meanwhile, Maya and Elliott fret over whether their marriage is legal or not and end up seeking out the help of the cult's strange lawyer, Larry. Larry successfully annuls the marriage, but the two are left still unsure about the possible future implications of the whole affair.

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.

Finch is upset because Adrienne is in Europe modeling and it's his first weekend away from her. Maya tries to convince Nina that the moon landing wasn't a hoax. Elliott is blackmailed into hiring a sleazy photographer as his assistant because the guy has a picture of Elliott having sex with Adrienne.

Adrienne's hand-model friend tries to make Finch look like a jealous husband. Nina does community service.

Finch realizes that he and Adrienne are very different from one another and begins to doubt their marriage. Meanwhile, Jack asks Maya to do the annual employee evaluations.

While attending one of Nina's sex addict therapy sessions, Finch overhears ex-wife Adrienne telling the story of a recurring fantasy: Finch in a pirate suit. He soon sneaks into her apartment to try it out, only to discover her new boyfriend: a cop. Meanwhile, Elliott and Maya struggle against Jack's intimidation to buy cookies for his daughter's private school.