The Same Side of Rejection Street (2000)

Two strangers, a vagrant and a woman from middle-class life, discover they are both social outcasts and find a measure of personal redemption in each other. She is a former telemarketer struggling with self-worth seeking employment, while he is an articulate man with a past and no fixed place to go. Both feel abandoned – she by her parents, he by his family. Drawn together by this shared sense of isolation, they embark on a day-long journey through the city, sharing their lives, beliefs, sorrows, and fears, slowly building trust. As they travel, a question arises: where is he taking her? Meanwhile, she is being relentlessly pursued by a software engineer who is deeply in love with her, and who previously sabotaged her career when she rejected him.