Kissing Jessica Stein (2002)
Starring Jennifer Westfeldt, Heather Juergensen, Tovah Feldshuh, Scott Cohen, Jackie Hoffman, Jon Hamm, Ben Weber, Brian Stepanek, David Aaron Baker, Esther Wurmfeld, Hillel Friedman, Jennifer Carta, Idina Menzel, Vinny Vella, John Cariani, Kevin Sussman, Jim J. Bullock, Hayden Adams, Christopher Berger, Alysia Reiner, Carson Elrod, Michael Mastro, Tibor Feldman, Michael Showalter, Michael Ealy, Allen Fitzpatrick, Julie Lauren, Jimmy Palumbo, Ilana Levine, Naomi Scott
IHBM7.5Very good
Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.
My review · Reviewed 08/05/2021
While this film touches on same-sex relationships I think its strength is in showing that - regardless of gender or sexual orientation - dating and relationships are heard. The two leads have a fantastic chemistry together and they are a joy to watch. I particularly enjoyed the ending - I thought it was perfect. I watched this more than 20 years after its debut - it is interesting to see so many future stars playing bit roles. While this movie got much more critical acclaim I think Jennifer Westfeldt's Ira & Abby might be just a bit better.