Jake Gyllenhaal's first public relationship was with singer Jenny Lewis. According to Us Weekly, the two dated in 2001, just as Gyllenhaal's acting career began taking off. When they dated, Lewis was the lead singer of the indie rock band Rilo Kiley. It's unknown when Gyllenhaal and Lewis officially broke up, but the two did keep in touch after their split. He brought Lewis as his date to the 2011 Golden Globes, though just as friends. At the time, Gyllenhaal was nominated for best actor in a musical or comedy for his role as Jamie Randall in "Love & Other Drugs."