Deborah Lipp

Kissing Jessica Stein (2001) 10/10
Jessica Stein (Jennifer Westfeldt) is a neurotic, brainy single woman seeking a man. Helen Cooper (Heather Jurgensen) is a sexually voracious woman eager to try the one thing she hasn’t tried: sex with a woman. Despite Jessica’s misgivings, they tentatively enter into a relationship.

This is one of my favorite movies, and I’ve seen it several times. Looking back, I see I’ve included it in Tuesday Trivia no less than three times. Yet I’ve never reviewed it here! It’s come up in conversation lately, since I’m going to L.A. and might be meeting Jon Hamm, (!) and Jennifer Westfeldt is his long-time girlfriend (Hamm has a small role in the movie). So, having said how much I loved it during the day, we sat down and watched it this evening.

It has all the great things you could want in a romantic comedy. It is witty, it is character-driven; populated by real people with real lives; every supporting player has motivation and personality. Take Jessica’s friend Joan (Jackie Hoffman). She’s riotously funny, and moves the plot along in exactly the way a conveniently-placed friend must. She’s also a fleshed-out person with her own trajectory in life.

Speaking of characters, Tovah Feldshuh as Jessica’s mother really enriches this movie. She only ever gets to play the one role in movies, but she’s magical in it every time.

Kissing Jessica Stein is frankly, boldly sexual, and very funny about sex. I have to say that “I was surprised to learn that lesbians accessorized,” is one of my all-time favorite quotes, and there is a funny bit about blow-jobs that brings tears to my eyes.

What gets me most about it is that it’s one of those movies, like The Object of My Affection (but way better), that explores the strange gray region between friendship and romance; between love and “love,” and does it brilliantly.