Jessica Stein, a typical neurotic Jewish Princess New Yorker (who, for some reason, movies have always thought are much more interesting than Gretel, bland farm girl from Kansas), has given up on the dating game. After a serious of truly awful dates with men, she peruses the personals with her best work buddy Joan. Joan reads one aloud that sounds perfect! Except... oh, it's in the "Women Seeking Women" section. After a pause, Jessica sneakily decides what the hell, and secretly answers the ad out of curiosity.
Enter Helen, an art dealer, who has tired of her own numerous affairs with men, who has placed the ad with the help of her gay best friends. Helen and Jessica click immediately, mostly in the "gosh we have a lot in common, and you're really cool" way, but also in the "I'm vaguely curious still, and I wonder if there is romantic possibility" way. Thus begins a sharp and witty romantic comedy, as these two women stumble and grope their way into a relationship.
I remember thinking mid-way through the movie, "This dialogue is so great... wouldn't it be cool if the leads actually wrote the screenplay?" And guess what? Jennifer Westfeldt (Jessica) and Heather Juergensen (Helen) were indeed the screenwriters, basing it on an off-Broadway play of theirs called Lipschtick. Their delivery and rapport is so natural, that it is an absolute delight to watch.
The film also has a strong supporting cast, with Scott Cohen as pining Josh, Jessica's college-ex and now co-worker at the publishing firm where she works, Jackie Hoffman as Joan, Jessica's hilariously supportive best friend, and especially Tovah Feldshuh as Jessica's not-so-typical Jewish mom. Feldshuh rises above what could have easily been a shrieking, arm-waving stereotypical role, but she infuses the character with depth and soul that she runs off with the most emotionally touching scene in the film.
With a splash of Woody Allen, Sex in the City, and Phoebe-from-Friends quirkiness, Kissing Jessica Stein will appeal to anyone who has an appreciation for smart, sassy, and funny romantic comedies.
If you own the DVD already (which I did, because I really love this movie), the Blu-ray release offers the same extras. There are deleted scenes, including an impressive rambling monologue by Jessica to another bad date, while they sit in a rowboat in a lake in Central Park, as well as some funny outtakes by Esther Wurmfeld, who plays Jessica's Grandma Esther. A "making of" featurette has Heather Juergensen and Jennifer Westfeldt visiting filming locations, reminiscing, and chatting about the evolution of the film. Writers/actors Juergensen and Westfeldt do a feature commentary, plus there is an additional commentary by Director Charles Herman-Wurmfeld and Cinematographer Lawrence Sher. Finally, there is a theatrical trailer.