Jessica Stein

Living… in the barren wasteland of New York dating scene. It seems like all the single guys left on the island of Manhattan are either horny, pathetic, or a combination of both.

Profession… copy editor for the New York Tribune. It’s Jessica’s job to find mistakes, and she worries that this is a trait that she carries into her personal life, too. As her coworker Josh points out, the problem may not be with New York’s single men, but with Jessica herself.

Interests… painting. Jessica, an insomniac, spends her sleepless nights at her easel.

Relationship Status… seems perilous. Jessica wants a man to fulfill her dreams, but she just can’t seem to find the right one. To add to everything, she’s got her mother breathing down her back to find a nice Jewish boy to settle down with. It’s only when Jessica meets bisexual art gallerist Helen Cooper that she begins to feel a bit more secure – if a little less sure of herself.

Challenge… keeping her experimental sexual relationship with Helen a secret from her conservative parents and her curious colleagues. Jessica is not quite sure that she’s a lesbian for good, but she enjoys spending time with Helen and treasures their relationship.

Personality… nervous, witty and a bit of a snob. Jessica’s expectations tend to be quite high, perhaps unrealistically so. Whenever she thinks she’s met the right guy, she always finds that he can never live up to her standards: “I think that’s been my big thing: not smart or not funny. Or… not smart and not funny.”