Kissing Jessica Stein (2002)
Directed by Charles Herman-Wurmfeld
Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.
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What critics compared Kissing Jessica Stein to
Other filmmakers and actors have been able to pull off this type of self-aware character in a far more accessible way--Jennifer Westfeldt of "Kissing Jessica Stein" for instance and even Dunham on "Girls"-- but not being able to feel any sort of connection to a character who appears in every single scene really holds "Obvious Child" back in a big way.
Supporting performances are also good and enjoyable, with Tovah Feldshuh ("A Walk on the Moon," "Happy Accidents") playing Jessica's over-involved, matchmaker mother (who shares the film's best, understated scene with Westfeldt), Jackie Hoffman ("Mo Money," "Freaky Friday") as her inquisitive and supportive coworker, and Scott Cohen ("Jacob's Ladder," "Private Parts") playing her former boyfriend and current boss.
I think we can agree that the high water mark for modern, post-Annie Hall romantic comedies thus far has probably been When Harry Met Sally... with a few memorable attempts in-between like Roxanne, Groundhog Day, Four Weddings and a Funeral, While You Were Sleeping and Chasing Amy.