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Jessica Stein (Jennifer Westfeldt) is an attractive single in New York City. She's twenty-eight and her inability to find a suitable man is driving her mother, Judy Stein (Tovah Feldshuh), crazy. Jessica isn't too thrilled either, as she's a bit of a perfectionist - appropriately employed as a copy editor for the Tribune - and it's not clear as we accompany her on a series of disastrous dates whether these dysfunctional men could possibly be so atrocious or if we're seeing them through Jessica's critical eyes. Perhaps, thinks Jessica, she should try something else? Attracted to a personal ad written by someone with the intellectual and artistic sensibility that Jessica has been seeking, there's only one slightly inconvenient detail: the ad is in the women-seeking-women section.

With great trepidation, Jessica arranges to meet the ad's author, Helen Cooper (Heather Juergensen), at a bar for an after work drink. Hesitation turns to curiosity, curiosity to dinner, dinner to intrigue as the heterosexual Jessica decides to have a relationship - physical and otherwise - with this woman. Helen is the more experienced of the two, secure in her sexuality and having experimented with a bisexual lifestyle. Under normal circumstances, Jessica is neurotic enough, but she achieves new heights of instability dealing with the discomfort of her exploration and hiding details from family and friends - particularly Josh Myers (Scott Cohen), her boss and former college boyfriend, and Joan (Jackie Hoffman), her pregnant office mate. Helen runs an art gallery in the Village, and one of her gay coworkers and his significant other - Sebastian (Carson Elrod) and Martin (Michael Mastro) - lend a voice to a controversy that emerged when the play first appeared off-Broadway.

Is homosexuality a genetically inherited preference or can it be a choice? Many members of the gay community objected to the suggestion. Such weighty issues aside, this is a delightful film, peppered with great humor that skewers the dating scene and offers some clever ethnic satire. The two lead actresses work wonderfully together; I suspect that their off-screen friendship helped make their onscreen relationship and intimacy more believable. I can't possibly know if they intended to emulate other familiar roles, but as I watched the film, Heather Juergensen's Helen Cooper reminded me of Kim Cattrall's Samantha Jones (Sex in the City) and Jennifer Westfeldt's Jessica Stein could easily be a more intellectual version of Diane Keaton's Annie Hall, right down to her funky hat at 0:7:29 (chapter 3).

Video: How Does The Disc Look?

The film's theatrical aspect ratio of 1.85:1 is presented in anamorphic video. Many of the scenes are shot at night or in dimly lit rooms, so the overall impression is dark. Blacks are deep and rich; shadow detail is moderate. Yet the feel of the film is rather warm, with a lovely color accuracy reflected in natural skin tones and the occasional vivid primary color. Detail and textures are reasonable but the transfer is marred by intrusive edge halos in scenes that contain objects of high or even moderate contrast. For example, a cordless phone antenna at 0:14:56 shows one or two cycles of ringing along its length, and a Central Park lamp silhouetted against the sky is no less messy. () Fortunately, these disturbing flaws are not obvious in most of the scenes; they simply destroy the illusion of film. I noticed no other compression artifacts.

Audio: How Does The Disc Sound?

The Dolby Digital 5.1 track is quite nice. Musical source tracks are accurately reproduced. I particularly liked the solo acoustic guitar at 1:08:00; the dry recording has great presence. It's in the music that some deep bass may be heard. Sound effects are not an issue; this is, after all, a romantic comedy. Surround effects are subtle and limited to environmental sounds, indicative of the film's underlying affection for New York City. The all-important dialog remains crystal clear throughout.

The alternate language track is in Spanish, and the audio is supported by English and Spanish subtitles and English Closed Captions.

Supplements: What Goodies Are There?

There are two feature-length, screen specific commentaries here: one by director Charles Herman-Wurmfeld and cinematographer Lawrence Sher; and, the other by costars, co-writers, and co-producers Jennifer Westfeldt and Heather Juergensen. Herman- Wurmfeld and Sher concentrate on the making of the film. The discussion is a tad technical, which I always enjoy. They touch upon locations, shooting challenges, and the esthetics of setups. I liked their commentary, but it was a bit dry compared to the warm and more intimate dialog by the women.

Westfeldt and Juergensen are delightfully chatty, clearly proud of their work and overwhelmed by the opportunity to have brought their vision to the screen and the subsequent praise. Their narration begins with the background and history of the film, but the focus is on a discussion of writing, character and story arc development, and an expression of gratitude for all the borrowed locations and cameos, so critical when the budget is tight. They describe the music selections, the pressures of time and limited funds, and enjoy sharing anecdotes from the set with the viewers. They talk and laugh, amusing one another with their reminisces, and we're made comfortable by their openness and candor.

There are ten deleted scenes that were either cut for flow or simply because they were outtakes. The mistakes are, of course, great fun; it's always a pleasure to watch the players crackup onscreen. The scenes may be played with or without commentary by Jennifer Westfeldt and Heather Juergensen. They are presented in messy non-anamorphic widescreen.

The women take us on a tour of locations, including the ArcLight Theater where it all began, in a featurette cleverly entitled The Making of Kissing Jessica Stein (8:48). The stars describe their characters and the premise of the plot, and generally charm us. Specific scenes are described in the context of visiting where they were shot, and the short featurette is peppered with many excerpts from the film. There is no mutual backslapping, just a well produced short that is slightly more informative than a theatrical trailer.

A full screen theatrical trailer is also included. The feature is organized into twenty-four chapter stops.

DVD-ROM Exclusives: What do you get when you pop the disc in your PC?

Nothing happens at all; there are no DVD-ROM features, either.

Parting Thoughts