Roberta (1999)

When Jonathan Fishman, a young Manhattan computer specialist randomly encounters a prostitute he is shocked to recognize her as Roberta whom he knew when they were both children. To the dismay of his friends, his business partner and his new girlfriend Judy, Jonathan decides to help Roberta off the streets by moving her into his apartment and teaching her the skills necessary to find an office job. What begins as a seemingly altruistic gesture reveals itself as an unwavering obsession, and his life slowly unravels.