Fed Up With Men–Date a Woman!rHeather Juergensen and Jennifer Westfeldt
Disclaimer–I LOVE "Kissing Jessica Stein"! The film is a bit dated (2002) and most young women, particularly young lesbians, probably can't identify with it. But for its time, it was a groundbreaker. It was one of the first mainstream films to show a realistic lesbian relationship and still one of the funniest I've seen.
Jessica Stein (Jennifer Westfeldt) is a neurotic, late 20's, nice Jewish girl who cannot find a man who meets her standards. She's a sensitive soul who loves books and poetry and paints as a hobby. She works for her ex-boyfriend, Josh Myers (Scott Cohen), at a New York newspaper. Her friend, Joan, (Jackie Hoffman, who practically steals the movie with her overt curiosity in everything lesbian!) reads a dating ad in the local newspaper that starts off with a Rilke quote, (For those of you who don't know Rilke, look him up. He wrote beautiful poetry.) and Jessica is immediately interested. Joan apologizes and tells her it's women seeking women, but Jessica is intrigued enough to reply to the ad. Helen (Heather Juergensen), who is the curator for an art gallery, has been dating three men at once and decides she wants to try being with a woman. Her gay friends find the Rilke quote for her and help her write the ad.
Jessica and Helen are made for each other, but, Jessica in particular, has to step out of who she thinks she is to become who she really is with Helen. Between Jessica's mother continually trying to set her up with "nice Jewish men", Helen trying to get Jessica past first base and Jessica trying to "do" being a lesbian right, the only thing that can ensue is hilarity. The music is great, the cinematographer loves New York and I always laugh out loud at the one liners, of which there are many!
Do yourself a favor and rent or stream this movie from Netflix or Amazon. You'll laugh and cry and be grateful for how far we've come since this movie was made.