Connor Mead is a famous photographer and womanizer. After breaking up with three women simultaneously on a conference call to save time, he travels to his late uncle Wayne's estate in
Newport, Rhode Island, to attend the wedding of his younger brother Paul to Sandra. There, he becomes reacquainted with Jenny Perotti, the only woman who captured his heart. At the rehearsal dinner, Connor delivers a drunken speech and makes a pass at Sandra's attractive and flirtatious mother, Vonda, and also unintentionally offends her ex-husband, the stern Sergeant Volkom, Sandra's father. He is then visited by the ghost of the inveterate
playboy Wayne, who warns Connor that he will be visited by three ghosts who will lead him through his romantic past, present, and future. The first is the "Ghost of Girlfriends Past" in the form of Allison, his first lover. They revisit scenes from his past, focusing on his relationship with Jenny. She and Connor were very close at school; she gave him his first
instant camera which he used to take her picture, promising to keep it forever, and even was there for Connor when his parents died. By
middle school, they were on the verge of romance, but Connor's hesitation at a dance caused Jenny to dance with and kiss another boy. Wayne, now Connor and Paul's legal guardian, advised a heartbroken Connor to avoid romance at all costs in order not to feel such pain again, and began to teach him his techniques as a pickup artist. When he next saw Jenny, he ignored her in favor of Allison. Several years later, Connor and Jenny met again and rekindled their romance. After spending the night together, Connor realized that he was falling in love and panicked, leaving Jenny to wake up alone and broken-hearted. Back in the present, Connor accidentally destroys the wedding cake and fails to reconcile with Jenny. He is confronted by the "Ghost of Girlfriends Present" in the form of his assistant Melanie, who shows him the other members of the wedding party making fun of his shallow lifestyle. Paul expresses his love for Connor, noting all of the sacrifices that Connor made in order to take care of him when their parents died, and his hope that he will someday improve. Meanwhile, Jenny is being comforted by Brad, which upsets Connor. Melanie and his newly jilted trio of lovers discuss his lack of empathy. Sandra hears of Connor's accidental revelation that Paul slept with one of her bridesmaids early in their relationship, and furiously confronts Paul. A returned Connor attempts to mend the situation, but Paul tells him to leave. He is visited by the "Ghost of Girlfriends Future", who takes him forward in time to see that Jenny marries Brad while both Connor and Paul remain alone. Further in the future, Paul is the only mourner at Connor's funeral. Wayne appears and tells Connor that this is his fate if he continues on the same path, pushing him into the grave to be buried by his many ex-girlfriends. Waking up in bed, Connor is relieved to find it is early on the day of the wedding, but discovers that Sandra has called it off and departed. Intercepting her car, Connor convinces her to forgive Paul, saying that the pain of heartbreak is outweighed by the regret of never risking one's heart in the first place. At the restored festivities—where he serves as wedding photographer—Connor reconciles with Jenny by showing her the picture he still carries of her. They kiss and dance in the snow to the same song Connor once hesitated to ask her to dance to. His work complete, Uncle Wayne strikes out with the Ghost of Girlfriends Future, tries to hit on Melanie before her corporeally present counterpart dances with Brad, and is finally rejected by Allison, the Ghost of Girlfriends Past, who still appears 16. ==Cast==