20th Century Fox/ABC sitcom Two Guys, a Girl and a Pizza Place, alongside Ryan Reynolds, Traylor Howard and Richard Ruccolo. Kissing Jessica Stein In 1997 Westfeldt co-wrote and co-starred with Heather Juergensen in an Off-Broadway play based on a series of sketches called Lipschtick: The Story of Two Women Seeking The Perfect Shade, which caught the attention of major Hollywood studios. The play was optioned by Radar Pictures to be made into a film, but after two years of studio development, Westfeldt and Juergensen bought back the rights to the script and decided to make the film independently. Kissing Jessica Stein debuted at the LA International Film Festival in 2001, where it won the Audience Award for Best Feature, and a Special Jury Award for Writing and Acting for Westfeldt and Juergensen. The film was released by Fox Searchlight Pictures in March 2002. Westfeldt received the Golden Satellite Award for Best Actress in a Musical or Comedy for her role as Jessica, and an Indie Spirit Nomination for Best First Screenplay. The film won the Audience Favorites Award at the Chicago International Film Festival, the Audience Award at the Miami Film Festival, Best Feature at the Louisville Jewish Film Festival, and the GLAAD Media Award, and it was included on more than a dozen top ten lists in 2002. Variety wrote, "A fresh take on sex and the single girl, this buoyant, well-crafted romantic comedy blends pitch-perfect performances with deliciously smart writing." In Newsweek David Ansen said the film "knows what it wants, what its limits are, and delivers its delights accordingly." In 2014, The Advocate listed the movie as an essential film for LGBTQ+ viewers that "encourages exploration and self-awareness." In 2020, Kvellar writer Mara Reinstein looked back on the impact that this "authentic" and "nuanced" movie had, writing, "I can't overstate how much Kissing Jessica Stein pioneered the gay rom-com." Other film work Westfeldt's next feature, Ira & Abby, marked her first solo screenwriting effort. The film debuted at the Los Angeles Film Festival in 2006, where it won the Audience Award for Best Feature. It was acquired by Magnolia Pictures and released in the fall of 2007 to strong reviews. Westfeldt won Best Actress at the HBO U.S. Comedy Arts Festival in Aspen in 2006 for her performance as Abby, where Ira & Abby also took home the Jury Prize for Best Feature. The film won Audience