Celebrity photographer Connor Mead is a renowned womanizer who disdains the idea of true love and marriage. On the eve of his younger brother Paul's wedding, Connor's disdain for romance leads him to vocally debunk the concept of matrimony to the wedding guests, causing an uproar, particularly unsettling the bride. However, his uncompromising lifestyle faces an unexpected challenge when he is visited by the ghost of his late uncle Wayne, a larger-than-life figure who once lived a life similar to Connor's but now comes bearing a warning. Wayne informs Connor that he will be haunted by three spirits over the course of the evening: the Ghosts of Girlfriends Past, Present, and Yet to Come.

These spectral visits embark Connor on a journey through his past relationships, starting with his first love all the way to the present. Each ghostly encounter reveals the depth of how his flippant attitude towards relationships has affected himself and the women he has been with. As he travels through time, Connor is confronted with the reality of his actions and the hurt he has caused. With each revelation, he is compelled to reevaluate his life choices, beliefs about love, and the way he treats others, especially his current romantic interest, who has always been significantly important to him. Through this introspective journey, Connor is faced with the pivotal question of whether he can redeem himself and alter his path to avoid a lonely, loveless future.