Connor Mead (Matthew McConaughey) is a famous photographer who regularly uses women, only to leave them behind before the night is over. Jenny Perotti (Jennifer Garner) is Connor’s childhood love, who also happens to be the maid of honor at Connor’s brother’s wedding. When the two see each other at the wedding rehearsal dinner, sparks fly with a series of aggressive conversations and lingering feelings from their old relationship. Connor grows tired of Jenny’s jabs, and wanders upstairs to find the owner of the home, his Uncle Wayne (Michael Douglas) pouring himself a drink. Uncle Wayne warns Connor not to become old and lonely like he was, and that he will be visited be three ghosts that night. Freaked out and drunk from the party, Connor retires to his room where he finds a teenager waiting for him. She turns out to be the Ghost of Girlfriends Past, and takes Connor through his life story with women. After a long night revisiting his past, Connor makes a leap for the only girl that ever mattered to him.