[2] Twenty-eight-year-old Jessica Stein is an attractive, Jewish, neurotic copy editor at a New York City newspaper.

Her brother Dan has just gotten engaged, her best friend Joan is about to start a family, and her mother Judy is worried that Jessica will end up alone.

Dissatisfied with unfulfilling sex with men, Helen is looking to try something different and decides to experiment with dating women at the encouragement of her gay friends.

The usually uptight Jessica gradually becomes more happy, confident, and carefree; this is noticed at her workplace and attracts interest from her boss, Josh.

The two of them are happy together, but Jessica stays closeted about her new relationship, refusing to bring Helen as her date to Dan's wedding for fear of what others will think.

As Dan's wedding approaches, Jessica sinks into a deep depression and goes to see Judy, who tells her that she is a perfectionist who always quits things if they are not perfect, even if they make her happy.

She puts up fliers in a bookstore seeking a new roommate, missing the flirtatious interest of the attractive store owner.

The two filmmakers decided to eliminate the nine or ten scenes featuring the Twin Towers because they were not integral to the story and distracted from it.

"[6] Metacritic, which uses a weighted average, assigned the film a score of 72 out of 100, based on 36 critics, indicating "generally favorable" reviews.

"[8] In the book Sexual Fluidity: Understanding Women's Love and Desire, Lisa M. Diamond cites the film as a notable example of female sexual fluidity in popular culture, writing that it "depicts a lesbian becoming involved with a man, contrary to the more widespread depictions of heterosexual women becoming involved in same-sex relationships.