Kissing Jessica Stein

Kissing Jessica Stein is a romantic comedy that follows the story of Jessica, a successful but neurotic Jewish copy editor living in New York City. After a series of disastrous blind dates, Jessica discovers a personal ad placed by Helen, a thirtysomething art gallerist who is looking to experiment with dating women. Despite her initial hesitation, Jessica replies to the ad and the two women hit it off, beginning a romantic relationship that challenges their assumptions about love and happiness. As they navigate their new relationship, Jessica must confront her fears and insecurities, while Helen must confront her own feelings of love and commitment. With a cast of colorful characters and a witty, engaging script, Kissing Jessica Stein is a heartwarming and hilarious film that explores the complexities of love and relationships in the modern age.

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Some movies that have similar genres and were produced around the same time as Kissing Jessica Stein include Old School, Napoleon Dynamite, Serving Sara, Me, Myself & Irene, Count Axel, Anchorman: The Legend of Ron Burgundy.