Ghosts of Girlfriends Past (2009)

Connor Mead, a notorious bachelor and successful photographer, lives a life free of commitment, easily breaking hearts without remorse. On the eve of his brother’s wedding, he’s visited by the ghost of his late uncle Wayne, a playboy himself, who warns Connor about his life choices. Guided by the ghosts of girlfriends past, present, and future, Connor is forced to confront his broken relationships and his unresolved feelings for Jenny, his childhood friend and former love. Through a series of humorous and eye-opening encounters, he realizes the cost of his careless ways and the importance of love, ultimately transforming his views on commitment and rekindling his connection with Jenny.