Connor Mead, a talented photographer known for his tendency to juggle numerous romantic entanglements, finds himself at a pivotal moment as he attends the wedding of his brother, Paul, to Sandra at their late uncle Wayne's estate. Amidst the jubilant celebrations, Connor unexpectedly reconnects with Jenny Perotti, the one woman who truly captured his heart. However, this chance meeting is soon interrupted by a series of unexpected ghostly visits from the spirit of Uncle Wayne.
Among the first of these supernatural visits is the "Ghost of Girlfriends Past," represented by Allison, Connor's first love. She takes him on a reflective journey through his previous relationships, particularly spotlighting key moments with Jenny. Flashbacks reveal their shared high school experiences, including a significant memory tied to the instant camera Jenny had given Connor, a memento of their inevitable bond. As this narrative unfolds, we see how the past still clings to Connor despite his attempts to move on.
Uncle Wayne’s ghost offers Connor some poignant advice about relationships: to avoid them entirely in order to evade the pain of heartbreak. Consequently, Connor immerses himself in the art of seduction, adopting his uncle's strategies while avoiding Jenny whenever possible. However, his efforts become increasingly complex as his feelings for her deepen, ultimately leading to him fleeing from her once again, leaving Jenny feeling desolate and rejected.
In a frantic present, Connor's misadventures reach a peak when a mishap occurs with the wedding cake. As he attempts to reconcile with Jenny, he is confronted by the "Ghost of Girlfriends Present," represented by his loyal assistant, Melanie. She unveils the harsh reality of Connor's superficial life, where his emotional disconnect is ridiculed by other partygoers.
At this critical juncture, Paul expresses a heartfelt desire for his brother to change and genuinely connect with others. Meanwhile, Jenny finds solace in Brad's arms, intensifying Connor's sense of loneliness and highlighting his own emotional void, as summed up by Melanie and his trio of previously spurned lovers. The situation spirals further when Sandra learns about a past indiscretion involving Paul, leading to an explosive confrontation. Even as Connor tries to intervene, he is pushed away by Paul.
The narrative takes a darker turn when the "Ghost of Girlfriends Future" appears, propelling Paul into a bleak vision where Jenny marries Brad, leaving Connor isolated and alone. A chilling glimpse into the future shows Paul mourning at Connor's funeral, bringing home the gravity of the impact of his choices. Urged by Wayne's wisdom, Connor is compelled to reassess his life choices, leading him to a waking moment where he realizes his time to change has not passed.
When Connor finds that Sandra has called off her wedding to Paul, he rushes to persuade her to reconsider. Emphasizing the greater sorrow attached to not loving than the pain of heartbreak, he successfully mediates peace. He quickly re-integrates into the festivities, stepping up as an unconventional wedding photographer, and at last shares a treasured photograph with Jenny, reigniting their connection. In a beautiful moment under a snow-kissed sky, they dance to a familiar song that once kept him from asking her to join.
As the day concludes, Uncle Wayne, now reunited with the “Ghost of Girlfriends Future,” attempts to charm Melanie, but faces rejection from the comforting presence of Allison, even after all these years. This whimsical conclusion highlights the enduring influence of love, loss, and the opportunity for redemption.
