Roberta (1999)

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Jonathan (Kevin Corrigan) is a computer expert who is a bit shy and lonely, though he's recently begun courting a schoolteacher named Judy (Amy Ryan). One night, Jonathan encounters a Latina prostitute named Roberta (Daisy Rojas), whom he's convinced he knew as a child. Jonathan is immediately… More Jonathan (Kevin Corrigan) is a computer expert who is a bit shy and lonely, though he's recently begun courting a schoolteacher named Judy (Amy Ryan). One night, Jonathan encounters a Latina prostitute named Roberta (Daisy Rojas), whom he's convinced he knew as a child. Jonathan is immediately obsessed with Roberta, though not for sex, which she finds more puzzling than reassuring. Jonathan soon moves Roberta into his apartment, begins teaching her office skills, even asking Judy to help take care of her. Roberta is not sure what to make of Jonathan's improvement program, her short-tempered pimp is decidedly unhappy with this arrangement, and Jonathan's friends try to convince him he's making a mistake. This socially and politically charged melodrama was shown in competition at the 1999 Sundance Film Festival. ~ Mark Deming, Rovi