Jessica Stein is the titular character in the 2001 romantic comedy Kissing Jessica Stein. Jessica is a copywriter by day, a fearless painter by night, and a perfectionist in every other aspect of her life. Dissuaded by a barrage of bad dates with men, on a whim, she answers a personal ad placed by a woman, Heather (Heather Juergensen), after resonating with the Rilke quote she chose for the advertisement. Jessica is played by Jennifer Westfeldt (who also co-wrote the screenplay with Juergensen).
Jessica displays a lot of the hesitation and angst that can plague someone exploring their queerness for the first time, which was groundbreaking and made palatable for straight audiences when the film first premiered. However, her emotional journey can often be read as “queer as conflict,” a thorny subject in queer media studies.
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