Ally Sims is a cynical, superficial, radio talk show hostess in Seattle who doesn't know the meaning of love despite the fact that she gives love advice over the airwaves, and has a loyal fiancée, named Matt, who is tolerant of her busy lifestyle. Two days before her wedding, Ally is visited by the ghost of Jackie Marley who shows Ally her past life boyfriends of the past, present, and future if she continues to live this stressful and shallow life.