Kissing Jessica Stein is a romantic comedy with a twist…of both heterosexuality and homosexuality.

Jessica is a journalist in New York City, working for a colleague – and former boyfriend. She has tried dating, but no one ever seems to truly measure up.

Whether they are simply strange, or not smart enough, Jessica is struggling to find anyone worth her attention.

Her brother is getting married, and one of her best work friends is incredibly pregnant. These two scenarios compound her loneliness and desire for romance.

One day, while going through the personal ads, Joan (aforementioned work friend) reads an ad that strikes Jessica’s fancy. There’s a problem, though. It was in the “women seeking women” section. On a whim, Jessica secretly contacts the woman who placed the ad.

Helen Cooper is a manager at a successful art gallery. She is surrounded by artists and creative people of all types. She has a harem of men, but none can truly satisfy the empty place in her heart. Looking for something substantial, Helen places a personal ad seeking out women.

Jessica and Helen meet, but their initial meeting doesn’t go as planned. Jessica tries to get away quickly. After several tries, Helen persuades her to join her for a drink. The two have great conversation and spontaneity. Things begin to get a little heated when Jessica asserts her confidence and knowledge of who she is.

Helen tries to tell her that she may not know what does or does not work until she tries and experiences things first hand. Jessica is hell-bent that she need not try everything to know what she does and does not like. Helen finally convinces her otherwise by kissing Jessica.

We now embark on a rather unusual and comical relationship. Fearful, Jessica can only take her physicality with Helen in small doses, so we watch the pair build up the relationship by taking small steps (they try kissing a few times, then they move up to using their hands, the next progression is to make out, and so on). It isn’t until they are staying at Jessica’s mother’s house one night that they finally reach a completely sexual relationship.

Both Jessica and Helen are flying sky high with each other. Life seems good, but Jessica isn’t ready to come out. Helen is always introduced as a friend, and no one close to her even knows the true nature of their relationship. Jessica’s façade begins to crumble when Joan runs into the pair at a grocery store. She becomes the first person to whom Jessica comes out.

In preparation for her brother’s wedding, Jessica is trying on a dress. Helen just happens to be passing by when she sees Jessica. She stops in to ask what the dress was for. At this moment, Helen just finds out about the upcoming nuptials and feels very excluded from Jessica and her family. Thus the relationship suffers.

The two women are both seen suffering the loss of the breakup. An especially poignant scene is an exchange between Jessica and her mother.

Jessica returns to Helen and invites her into her life completely.

Things seem to be going well for the couple, but as all of this is occurring, Josh, Jessica’s boss and former boyfriend realizes that he still loves her. At her brother’s wedding, Josh tells Jessica about his feelings for her, only to have them dashed when he learns that Helen is much more than a friend.

Jessica moves in with Helen, and all seems right with the world. Just like any relationship, though, things begin to fizzle, and neither woman is fully capable of maintaining it.

Jennifer Westfeldt brilliantly portrays Jessica Stein. Helen is played by Heather Juergensen. Tovah Feldshuh plays Jessica’s mother, Judy Stein. Jackie Hoffman and Scott Cohen round out the cast as Joan and Josh.

Kissing Jessica Stein is a fun, light-hearted look at self-discovery. It’s a cute romantic comedy that is easily entertaining. Even as a comedy, this movie reminds us that we never really know who we are: that our lives are a constant evolution and re-definition of self.