The Tollbooth(2006)

A Jewish family from Brooklyn is seen through the eyes of Sarabeth Cohen--a struggling painter in her first year out of art school. Sarabeth and her older sisters Becky and Raquel come of age and question the values of their traditional parents. Sarabeth's first revolutionary act is scoring a job as a waitress and moving across the river to Manhattan. Even though she is less than ten miles from her parents, and her bedroom is her sister's walk-in closet, she feels like a pioneer--ready to take on the New York art community, and maybe even the world. Though she would like to rebel, she is forced instead to learn from her family; Ruthie--her well-meaning but traditional-and-loud-about-it mother, Isaac--her holocaust-obsessed philosopher-quoting father, Becky--her lesbian medical-student sister, Raquel--her nurturing self-sacrificing sister and Howie--Raquel's sweet but always misguided husband. She also learns some tough lessons from Simon--her boyfriend from art school, who graduates and chooses the suburbs, a good job and an entertainment center over a life filled with uncertainty in New York City.