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| Matthew McConaughey | Connor |
| Jennifer Garner | Jenny |
| Michael Douglas | Uncle Wayne |
| Breckin Meyer | Paul |
| Lacey Chabert | Sandra |
| Robert Forster | Sarge |
| Anne Archer | Vonda |
| Emma Stone | Allison |
| Daniel Sunjata | Brad |
| Noureen DeWulf | Melanie |
| Camille Guaty | Donna |
| Rachel Boston | Deena |
| Amanda Walsh | Denice |
| Emily Foxler | Nadja |
| Catherine Haena Kim | Charlece |
| Noa Tishby | Kiki |
| Logan Miller | Teenage Connor |
| Christa B. Miller | Teenage Jenny |
| Olga Maliouk | Ghost of Girlfriends Future |
Celebrity photographer Connor Mead 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.
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