Jessica Stein (Jennifer Westfeldt) is a sensitive but entirely neurotic New Yorker who doesn't really like her job as a newspaper copy editor has trouble sleeping and is at her wits' end trying to find a man. Her Jewish mother (Tovah Feldshuh) is forever trying to fix her up but with no luck. Her boss Josh (Scott Cohen) is also constantly ribbing her about it. On a whim she answers an intriguing personal ad glossing over the fact it is in the "women seeking women" section and meets Helen Cooper (Heather Juergensen) a funky assistant museum curator who has had her fair share of mediocre heterosexual relationships. To Jessica's immense surprise she and Helen click instantly and spend a delightful evening of intelligent conversation which culminates in a kiss that titillates the reluctant Jessica. Suddenly Jessica has found the right person for her--that person just happens to be a girl. Can the straight Jessica really "go all the way"--literally and figuratively--with the bisexual Helen? Or is Jessica confusing romantic love with a truly meaningful friendship?
In a cast of mostly fresh faces the ensemble acting has a very insular feel to it--like we are watching a bunch of close friends get together to make a film. Westfeldt and Juergensen (who also co-wrote the script) are both New York actresses who have done mostly stage work. It's obvious there is a genuine chemistry between them. Westfeldt comes off quirky and sweet if maybe a tad too neurotic (she couldn't answer a simple question without a myriad of tics and stutters) while Juergensen plays the calm and collected "guy" very well. Cohen as Jesica's token romantic male interest does a decent job but plays it more smarmy than sexy at times. Jackie Hoffman (a voiceover actress) who plays Jessica's best friend Joan is a real kick. Not in any way classically pretty and pregnant through most of the film she is entirely refreshing. Her reaction to finding out Jessica is in a lesbian relationship is priceless. Also quite good is Feldshuh as Jessica's mother Judy. The only known actress in the film her scenes with Westfeldt are heartfelt especially when Judy embraces her daughter's chosen sexual preference.
This is a pleasant sometimes very funny film which manages to explore some interesting topics. Director Charles Herman-Wurmfeld relatively new to making films does foster a very close-knit feel with his shots and with the actors but it's writers/co-producers Westfeldt and Juergensen whose vision dictates the film. They tap into a question probably more than a few straight women have thought about--being with a women instead of a man. Jessica's first reaction as she admits is "Ew. Can't go there. Can't get excited " but then of course tries to anyway. Although you have to ask yourself why someone so together like Helen would have any interest in the totally messed-up Jessica--guess there wouldn't be a movie then. The problem is the film goes along in one direction--Jessica meeting Helen; Jessica and Helen dealing with their feelings; Jessica and Helen coming "out " so to speak--and then gives an ending that feels like an afterthought. It could have concluded more definitively.