A divorcing couple tries to maintain their friendship while they both pursue other people.

Celeste and Jesse have been best friends forever. They dated in high school, got married, and now they're getting divorced. Their best friends don't think they can maintain their friendship throughout the dissolution of their marriage, but Celeste and Jesse don't think there will be a problem. But that's before Jesse gets into a relationship that Celeste doesn't think he can handle, and Celeste finds it harder to move on than she originally thought.—napierslogs

For the long time that married Celeste and Jesse have known each other, being best friends has always been first and foremost, even now that they are officially separated for six months and headed toward divorce. They still hang out with each other as best friends every day, with Jesse living and working as a freelance graphic artist in Celeste's guest house. The separation and imminent divorce was largely Celeste's idea, she a successful social trend analyst, recently published author, and co-principle of a media consulting firm with her gay business partner, Scott. Driven Celeste could not be married to someone as lackadaisical toward work and earning money as Jesse, who is in no hurry to get more permanent and stable work even in his field, preferring his recreational activities and largely living off what Celeste earned. Their mutual friends, seeing how happy they still are whenever they are together, cannot understand why they are headed toward divorce. Jesse would still prefer to remain married to Celeste, he still seeing her as his soul mate. Things start to change in their relationship when Jesse, seeing the reality of the situation, is the first to move on from them as a couple, entering into a relationship with a woman named Veronica. Out of circumstance in the situation with Veronica, Jesse slowly transitions into being that mature human being that Celeste so wanted in him for their marriage. As such, Celeste works on two parallel tracks: to get Jesse back; or to enter into a relationship with someone as happy as Jesse and Veronica appear to be. Celeste may get a clearer picture of her own life in dealing with one of her new clients, teen pop sensation Riley Banks, a seemingly vapid and only moderately talented singer.—Huggo

During the opening credits, which have little or no audio except the music playing for all of it, Celeste and Jesse appear to be happy. However, after six years they have decided to separate. They are still friends and spend lots of time together. But he is a lazy bum, though likeable, and she has a successful career marketing celebrities, though she wishes all those celebrities actually had talent. His art, though, could end up being displayed in galleries. He also does art for her company. Their friends Tucker and Beth, who are getting married, point out that their relationship is annoying. Celeste and Jesse needs to move on and date other people. Mostly, the movie is Celeste and her misadventures in attempting to date, including one guy she meets doing yoga. And there are also career problems, including typical teenager Riley, who is shallow but not really spoiled, and not talented in Celeste's view. But the two end up having quite a special relationship anyway. Jesse, meanwhile, gets together with Veronica, who is pregnant with his child after a one-night stand.