Kissing Jessica Stein

Kissing Jessica Stein (2002) is an American romantic comedy you can watch online on iFILM. Jessica is a Jewish copy editor in New York with a specific problem: she goes on a lot of blind dates, and every man fails some test she cannot quite explain. Her friends are out of ideas. She is out of patience.

Then she answers a personal ad. It was placed by Helen Cooper, a thirtysomething art gallerist who has never labeled herself but is curious. Jessica has always labeled herself very clearly. The date goes better than anything she has been on in years.

The script was written by Jennifer Westfeldt and Heather Juergensen, who also play the leads — the chemistry is real because it was built into the material from the start. Directed by Charles Herman-Wurmfeld, the film is sharp about New York social life without being smug about it, and it takes both women seriously enough to let the ending be complicated. An early Jon Hamm appears in a supporting role. Stream Kissing Jessica Stein (2002) online on iFILM.