Failure to Launch (film)
2006
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Celebrity photographer Connor Mead (Matthew McConaughey) lives life in the fast lane, committed to bachelorhood and simultaneous relationships with multiple women. On the eve of his brother's wedding, Connor receives a visit from the spirits of his jilted lovers, who take him on an odyssey through his many failed relationships to try to find out what made him such a cad -- and if there is any hope of Connor finding true love. Wikipedia