Feeling Minnesota explores the tormented relationship between two brothers, Sam (Vincent D'Onofrio) and Jjaks, and the young woman, Freddie (Cameron Diaz), who comes between them. The story begins at the drab, unromantic wedding of Freddie and Sam, an embezzling accountant in a strip joint whom Freddie loathes. A tough young blonde who dreams of a better life in Las Vegas, Freddie is conned into marrying Sam as punishment for allegedly stealing from Red (Delroy Lindo), a small time crime boss.
Trapped and miserable, Freddie is soon intrigued by the arrival of Jjaks (Keanu Reeves), who reluctantly comes to the wedding at the insistence of his mother, Nora (Tuesday Weld). Just as he knew it would, Jjaks' encounter with his estranged family quickly disintegrates into the usual frustrating mess. His connection with the forlorn Freddie, however, is immediate and intense and before he knows what's hit him, the two are making love in the bathroom. Thus begins a passionate and painful love triangle as Sam and Jjaks go head to head for the girl they love. Dark, funny and poignant, Feeling Minnesota is the story of three volatile, imperfect people still holding out a desperate hope for love and a second chance at life.