In between working on her two wildly popular shows, Shear appeared in several films, playing bit parts in "It Could Happen to You" (1994) and "Living Out Loud" (1998), and even making a guest appearance as the "fake Monica" on NBC's "Friends" (1994). Shear also wrote for numerous publications such as The New York Times, Vogue, Glamour, Travel & Leisure and Psychology Today, as well as Underwire, an online magazine.

Born in Brooklyn to a firefighter and a cosmetics executive, Shear did not have an idyllic childhood. Weight problems and a persisting feeling that she was an outsider and a misfit kept Shear isolated from other children, forcing her to seek comfort in books and food. Her parents were always working when she and her sister were growing up, and adding to the issues of alienation and abandonment, the girls had to deal with their parents' divorce when they were very young. The difficulties in her life forced Shear to grow up much quicker than the average child. Shear went to work when she was only 12 years old, lying about her age so she could get a job as a hardware stork clerk. It was around this time that she also fell in love with the theater, having taken herself there when she was just 10 or 11 years old. Perhaps it was as a means of escape from her bleak childhood, but Shear decided to be an actress at a young age. Despite her enthusiasm, she found few directors willing to cast a big girl such as herself in any serious roles.

Unable to break into the business--despite the occasional bit part in an Off-Off-Broadway show--the fast-talking writer went to work as a volunteer at the Public Theater, where she met casting director Jim Nicola. Shear asked Nicola to help her find an agent, but Nicola suggested she try her hand at writing instead. He later introduced her to Ashley, who would one day direct "Blown Sideways Through Life".