
Connor Mead, played by Matthew McConaughey, is a high-profile celebrity photographer who thrives on living life at full speed. Devoted to his lifelong bachelorhood, he juggles simultaneous relationships with multiple women, embracing a carefree and commitment-free lifestyle. As he revels in his reputation and charm, Connor confidently dismisses the idea of true love, viewing it as unnecessary and amusing.
The story takes a pivotal turn on the eve of his younger brother Paul's wedding, when Connor's cynical attitude towards love casts a shadow over the celebrations. His behavior not only dampens the mood but deeply affects Jenny Perotti, portrayed by Jennifer Garner, the one woman who has always remained immune to his charms and holds a special place in his heart. This evening sets the stage for a profound transformation as Connor confronts the consequences of his choices and the people he has hurt along the way.
That very night, Connor receives an unexpected visit from the ghost of his late Uncle Wayne, a legendary ladies' man who once mentored him. Uncle Wayne brings an urgent message conveyed through three spectral guides who take Connor on a revealing journey through his romantic past, present, and potential future. Throughout this supernatural adventure, Connor is challenged to reflect on his life and consider whether he can change his ways and embrace the possibility of finding genuine love and lasting happiness.