Ghosts of Girlfriends Past 2009

Connor Mead (played by the inimitable), a renowned photographer with a penchant for bedding multiple women at once, finds himself attending the wedding of his brother Paul to Sandra at his late uncle Wayne’s estate. As he navigates the festivities, Connor is unexpectedly reunited with Jenny Perotti, the only woman who has ever truly captivated his heart. However, this chance encounter is soon overshadowed by a series of supernatural visitations from the ghost of Wayne himself.

The first spectral visitor is Allison, Connor’s initial paramour, who materializes as the “Ghost of Girlfriends Past.” This ethereal entity whisks Connor away on a journey through his romantic past, revisiting pivotal moments in his relationship with Jenny. We see glimpses of their high school days, where they shared a tender moment that foreshadowed a romance that was never meant to be. As the memories unfold, we are reminded of the instant camera that Jenny gifted Connor, which he promised to cherish forever - a symbol of the enduring connection between them.

Wayne’s ghost offers Connor some hard-won wisdom: to avoid romance at all costs in order to spare himself the agony of heartbreak. Instead, Connor devotes himself to mastering the art of seduction, learning from his uncle’s playbook and applying these newfound skills to ignore Jenny whenever they cross paths again. Their reconnection is short-lived, as Connor’s growing emotional attachment causes him to flee, leaving Jenny to awaken alone and broken-hearted once more.

Fast-forward to the present, where Connor’s antics culminate in a catastrophic mishap involving the wedding cake. As he struggles to make amends with Jenny, he is confronted by the “Ghost of Girlfriends Present” in the guise of his trusty assistant Melanie. This spectral guide reveals the stark reality of Connor’s shallow existence, as the other wedding party members mock his lack of empathy and genuine connections.

In this moment of reckoning, Paul shares a heartfelt expression of love for his brother, imploring him to transform and find true fulfillment. Meanwhile, Jenny seeks solace in the arms of Brad, leaving Connor feeling crestfallen and confronted with the cold, hard truth about his own emotional bankruptcy - as relayed by Melanie and his trio of recently jilted lovers.

As Sandra becomes privy to Connor’s unintentional disclosure that Paul had an illicit encounter with one of her bridesmaids early in their relationship, she unleashes a torrent of fury upon Paul. A remorseful Connor endeavours to soothe the situation, but Paul dismissively tells him to leave. In an eerie manifestation, the “Ghost of Girlfriends Future” materializes, whisking Paul forward in time to witness a dismal reality where Jenny marries Brad while he remains perpetually alone. A haunting vision unfolds further into the future, with Paul standing as the sole mourner at Connor’s funeral. As if conjured by Wayne’s words of wisdom, the latter appears and urges Connor to alter his trajectory, literally pushing him towards the grave, where his numerous ex-girlfriends await to bury him.

As Connor awakens in bed, he is initially relieved to find that it’s still early in the day, only to discover that Sandra has cancelled their wedding plans and departed. With a change of heart, Connor intercepts her car and persuades her to pardon Paul, emphasizing that the anguish of heartbreak pales in comparison to the regret of never risking one’s heart in the first place. Rejoined at the revitalized festivities – where he serves as an unconventional wedding photographer – Connor mends his relationship with Jenny by sharing a cherished photograph of her. They share a tender moment, embracing and dancing under the snow-kissed sky to the same song that once held him back from asking her to dance.

Upon completing his duties, Uncle Wayne embarks on a quest with the Ghost of Girlfriends Future, attempting to woo Melanie before her physical counterpart takes a spin with Brad. Ultimately, he meets rejection at the hands of Allison, the Ghost of Girlfriends Past, who still appears 16 years into the future.