Longe da Vista (1999)

In order to make some much-needed cash for himself, 65-year-old Portuguese prison inmate Eugenio impersonates a young woman and begins a romantic correspondence with a lonely Portuguese truck-driver living in Boston, convincing him that her tragic life has culminated in financial dire straits so he will send money. At first Eugenio's sister Idalina assists him in creating the character of Maria da Luz. Touched by her sweetness and apparent loving nature, the trucker willingly sends her money. When Idalina starts fearing they will be caught, she backs out of her arrangement with Eugenio who then convinces his young cellmate Vasco to help write the letters and even sends a picture of himself at age seven to "prove" that Maria has a young son. As prison life exacts an increasingly heavy toll upon Eugenio's health, his feminine alter-ego helps sustain him.