Actress/writer Jennifer Westfeldt graduated from Yale in the early ’90s, then spent over half a decade essaying minor on-stage parts in off-Broadway productions, before mounting a career as a television actress — typically with guest roles on series such as Judging Amy. She broke through to national acclaim, however, as a theatrical scribe, by co-authoring the now-legendary stage revue Lipschtick alongside writing partner Heather Juergensen. Comprised of a series of Nichols and May-like sketches connected by a loose narrative thread, this comedy detailed both women’s romantic foibles in attempting to find and date a decent man, until they discovered one another and tried out a lesbian relationship — tentatively. Despite its off-off-Broadway status, that production won the hearts of innumerable critics and ultimately yielded a low-budget film adaptation, written by and starring the pair, directed by Charles Herman-Wurmfeld, and retitled Kissing Jessica Stein (2001). The effort received enthusiastic reviews and swept up a plethora of festival awards.
Stein also paved the way for a much-anticipated follow-up, which arrived in 2006. As authored, this time around, by Westfeldt alone (sans Juergensen), Ira & Abby mined less overtly biographical territory. It told of a neurotic twentysomething (Chris Messina) who hastily enters nuptials with a young woman (Westfeldt), only to find his self-assurance violently shaken. Coinciding with the release of that picture, Westfeldt also tackled one of the two lead roles in the series Notes from the Underbelly — a sitcom about a couple (Westfeldt, Peter Cambor) birthing and raising their first child.