Harper Sloane (SARAH POLLEY) is a twenty-year-old, insecure woman who's set to attend Harvard, thus following in the footsteps of her family of lawyers, including mother Deborah (JEAN SMART), father Alan (FRANCIS GUINAN), and sister Susan (EMILY PROCTER).
Yet Harper doesn't feel as if she fits in, so when she meets Cornelius "Connie" Fitzpatrick (STEPHEN REA), the middle-aged photographer working at Susan's wedding, she's swept away by his laid back, self-assured ways and the fact that he doesn't treat her like an inferior.
When Harper visits Connie's office/loft apartment to pick up the wedding photos, he immediately sizes her up and sets out to lure her into his life, slowly but surely. With such low self esteem, she obviously falls for him rather quickly, and lying to her mother that she's moving in with her best friend, Patty (CARRIE PRESTON), instead moves in with Connie. With the only condition being that she pursue some creative endeavor in exchange for staying at his place, the two quickly begin a passionate romance, with her also serving as his photography apprentice.
She soon meets Connie's friends who occasionally meet to discuss philosophical matters. Among them is heavy drinker Zack (TRACY LETTS), as well as Billy (GINA GERSHON), an artist who later informs Harper that she -- like Billy before her -- is just one in a long line of young women to fall for Connie, who gives all of his paramours the nickname, "Guinevere."
As their relationship progresses and goes through its share of ups and downs, Harper must decide how to proceed, especially when everyone from Patty to her mother question the huge age difference between the two lovers.