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. In the years to come, Westfeldt would remain active on screen, appearing on shows like 24 and Notes from the Underbelly. In 2011, she wrote, directed, produced and starred in Friends with Kids (co-starring her then-longtime love, Jon Hamm).