Jessica Stein (Jennifer Westfeldt) is a cute 28-year-old copy editor who strikes out with date after date. "I'd like to represent you as your accountant and your boyfriend, if that's possible," one of her more nerdy dates tells her. Her boss, Josh Meyers (Scott Cohen), might seem a logical candidate if they didn't put so much negative energy into their bickering version of flirting.

One day, the nervous and high-strung Jessica decides on a lark to try something completely different. She answers an intriguing ad in the personals section of The Village Voice. Here comes the twist. The ad is in the woman-seeking-woman section of the paper. The ad was placed by an adventuresome, bi-curious female named Helen Cooper (Heather Juergensen). Helen is as free a spirit as Jessica is conservative. Helen, who wants to try everything and often, mockingly refers to Jessica as a "Jewish Sandra Dee."

Their first date almost never happens since Jessica runs out in an absolute panic. When their relationship, many dates later, finally gets physical, they are like a couple of young teens kissing for the first time. These scenes, full of giddy awkwardness, are the movie at its best. Although Helen would be happy to wear a "Want to be a Lesbian? Ask me how." button, Jessica stays as hidden in the back of the closet as possible. When the weather forces them to stay overnight with Jessica's mother, Judy (Tovah Feldshuh), Judy says that they will have to sleep together in Jessica's old room. Once in bed together for the first time in Jessica's childhood bed, their rush of erotic excitement is palpable. "I feel like we're going to be grounded," Helen confesses to Jessica.

After several false starts, the movie finally finds an ending that works. This comedy of manners and romance is a charmer that should have broad cross-over appeal to audiences, gay and straight.

KISSING JESSICA STEIN runs 1:34. It is rated R for "sexual content and language" and would be acceptable for most teenagers.