Charles (Charlie Sheen) is a successful graphic designer whose fame, money and charm have provided him with a seemingly perfect life. When his true love, a perplexing beauty named Ivana, suddenly breaks off their relationship, Charles' life falls apart, and he swirls into a downward spiral of doubt, confusion and reflection. With the support of his loyal intimates—Kirby (Jason Schwartzman), Saul (Bill Murray), and his sister, Izzy (Patricia Arquette)—he begins the hard road of self-evaluation to come to terms with a life without Ivana. The film begs the question: Is it possible to love and hate someone at the same time?