| Director | Demetri Martin, Dominique Choisy |
|---|---|
| Genre | comedy film |
| Country | United States |
| Budget | $950,000 |
| Box office | $254,536 |
Dean lives in Brooklyn and has recently lost his mother. His father, Robert, is having difficulty adjusting to being alone. Dean's ex-fiancée Michelle tries to give back the ring, as Dean has "un-proposed", but he refuses.
Dean's best friend from college Brett is getting married, and is actually the "second best" man behind Kevin. Dean's cat-obsessed friend Eric has also come from Los Angeles for the wedding. At the wedding, Dean's ex distracts him, and he drops the wedding ring. At the reception, Dean begins his best man speech, but gets interrupted by Kevin, who tries to assault him.
The next morning, Dean's dad announces he is selling the house. To postpone, Dean uses an excuse of an LA trip to meet with an ad agency who want to use his drawings. Frustrated by Dean's lack of engagement, his father has already brought in realtors Carol and Patrick, who he incorrectly assumes are married. Later Robert sees Carol's online dating profile on her PC, and he uses it to flirt with her.
Meanwhile the advertising agency puts Dean off by their idea to use his work in a deodorant ad. Dean excuses himself and leaves. Calling his LA friends, including Becca and Eric, he goes to a party, where he meets Nicky. He is immediately attracted to her and pursues her clumsily, despite her friend Jill blocking him. He gives Nicky his number, written on small notebook paper in a "twentieth-century way."
As Dean is flying out, Nicky's text invites him to the beach, so he gets off the plane and heads to meet her. Finding each other, they go to dinner. He kisses her at the end of the night. After an unsuccessful meetup with Nicky and Jill at an art gallery, Nicky tells Dean that she and Jill are going to San Francisco, and he asks if he and Eric can tag along. Just before a hike, Eric gets a call about a cat emergency and insists on flying home immediately.
Robert and Carol have been dating in New York. Returning from a play, Carol invites him to her apartment for coffee, but he declines because he is "still married." Meanwhile, Nicky spends the night with Dean, where he confesses he thinks he is in love with her, then mentions the failed engagement and his mother dying. In the morning, Nicky leaves him a "twentieth-century style" letter at the front desk, apologizing for not telling him she is separated from a current husband.
Dean returns to New York and finishes his book. Robert now lives in an apartment in the city. Dean apologizes for not being there, and finally reconciles with his dad. Dean sends a message and signed copy of his book to Eric, telling him of what he's learned about loss and healing. Robert sees Carol walking in his neighborhood, and they walk on together.