In the 1970s, successful graphic designer and ladies' man Charles Swan III (Sheen) is dumped by his girlfriend Ivana (Winnick), and it throws his life into a tailspin. He does not know whether he loves her or hates her or wants her back or never wants to see her again. Along with his best friend, Kirby (Schwartzman) and his manager, Saul (Murray), Charles starts to suffer from nightmares, fever dreams of past relationships and hits rock bottom as he tries to recover from the recent breakup and tries to turn his life around.