After a century of moving pictures, one of the greatest challenges to cinema, is saying something fresh, original, and new about humanity’s most basic need and quest: the pursuit of love. “Kissing Jessica Stein” expertly navigates dating hell, romantic love, bisexuality, and friendship.
Jessica Stein (Jennifer Westfeldt) is a neurotic but highly functional single girl in New York. Jessica is of an age where she might want to settle down but doesn’t want to “settle” for less than the right boy. Her mother tells her she’s being picky, while others feel the issue may be deeper: maybe no guy is good enough. When a co-worker reads a personal ad aloud that sends Jessica’s endorphins skyrocketing, she responds impulsively, yet is unsure of whether she is fully open to answering an ad in the section Women Seeking Women. Jessica meets Helen (Heather Juergensen), gets scared, and finally is seduced into having a drink with her. While seeming opposites, the two forge a friendship with innate sexual undertones. Jessica becomes caught between changing societal morays, wanting to please her friend, and her own animal desire.
Originally a skit, then a play, “Kissing Jessica Stein” was written by it’s female co-stars, and this very personal characterization is what helps make the film feel so real. Three years of writing, rehearsing, and performing “Jessica” together helped develop the film organically for Westfeldt and Juergensen. While there are often hindrances in transitioning from stage to screen, director Charles Herman-Wurmfeld does a wonderful job in keeping the movie from ever becoming “stage-y”. A true filmmaker, Herman-Wurmfeld adds cinematic language and filmic elements that immortalize the performances and text.
While the film missteps in a few small places, it’s charm, wit, and heart make “Kissing Jessica Stein” one of the few “must see” films of the year; quite an accomplishment for novice filmmakers.