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Based on the novel On Love by Alain de Botton, writer-director Julian Kemp's My Last Five Girlfriends traces the romantic journey of thirtysomething bachelor Duncan (Brendan Patricks. As the film opens, the despondent Duncan is apparently preparing to take his own life, but not before taking the time to send a message to the last five women he dated.
Taking the form of a whirlwind tour through Duncan World, the film is a comedic exploration of his failed relationships. First there's Wendy (Kelly Adams), who can't get over her ex. Then Duncan adapts a variety of different personalities in a failed effort to charm Olive (Jane March of The Lover).
His relationship with Rhona (Cécile Cassel) ends badly because he can't appreciate her sense of style. Things go more smoothly with Natalie (Edith Bukovics), but he pulls back when he begins to feel that they're moving too fast. After their breakup, he pursues Natalie's friend Gemma (Naomie Harris of the Pirates of the Caribbean sequels).
With Gemma, Duncan feels that he's learned from his past mistakes and found a potentially lasting and true love, but she seems reluctant to commit. My Last Five Girlfriends had its world premiere at the 2009 Tribeca Film Festival, where it was shown in the Discovery section.