Kissing Jessica Stein

Kissing Jessica Stein is a 2001 American independent romantic comedy film, written and coproduced by the films stars, Jennifer Westfeldt and Heather Juergensen. The film also stars Tovah Feldshuh and is directed by Charles HermanWurmfeld. It is also one of the first film appearances of actor Jon Hamm. The film is based on a scene from the 1997 offBroadway play by Westfeldt and Juergensen called Lipschtick.

Given some of the men Jessica is shown to be testdating at the start of the film, its no surprise shed want to fan out her prospects a little. As nervous as Jessica is about dating Helen, she realizes after a surprise kiss that a different experience can be good. Through the early part of their relationship, Jessica finds in Helen everything shed dreamed of finding in a man. They are compatible, they like many of the same things, and they are caring for one another. Even when Helen gets sickwhich she says earlier in the film never happens to herJessica is there to care for her.The only predicament for the relationship is Jessicas nervousness concerning samesex intimacy. Over the early weeks of their relationship, she and Helen slowly work on building up her confidence in this area by gradually extended makeout sessions. Eventually, they graduate to full intimacy, which is initiated by Jessica during an over night stay at her parents home in Scarsdale. In spite of Jessicas happiness with Helen, she keeps the relationship secret. Jessicas secrecy means that she has to endure scenes that would not happen had she been open about the two of them. One example occurs during a dinner to celebrate her brothers engagement. Her mother had invited an IBM executive in hopes of setting him up with Jessica. ........

Source: Wikipedia