At his younger brother's wedding, a committed bachelor/womanizer (McConaughey) is haunted by his romantic past. Matthew McConaughey ... Connor Jennifer Garner ... Jenny Lacey Chabert ... Sandra Emma Stone ... The Ghost of Girlfriends Past Christina Milian Noureen DeWulf ... Melanie / Ghost of Girlfriends Present Amanda Walsh ... Denise Michael Douglas ... Uncle Wayne Breckin Meyer ... Paul Robert Forster other cast: Anne Archer Daniel Sunjata ... Brad Camille Guaty ... Donna Tina Casciani ... Vargas Girl 3 Christa B. Allen ... Teenage Jenny Rachel Boston ... Dina Noa Tishby ... Kiki Annalaina Marks ... Vargas Girl 1 Emily Foxler ... Nadya Tom Kemp ... Minister Chi Muoi Lo ... James Rachelle Wood ... Model #1 Paul Cassell ... Wedding Guest #1 Catherine Haena Kim ... Charlece Erin Wyatt ... Model #2 Logan Miller ... Teenage Connor Stephen Russell ... Disinterested Minister Samantha Goober ... Marissa Cynthia Kirchner ... Vargas Girl 2 Chad Mountain ... DJ Alyssa McCourt ... Clarissa Kasey Russell ... Young Jenny Sam Byrne ... Pete Hastings Devin Brochu ... Young Connor Tia Shipman ... Model Kortney Adams ... Jenny's Colleague Albert M. Chan ... Sam Alexander Fagan ... Teenager #1 Lynn Clayton ... Connor's ex-wife Guy Guglielmi ... Unemployed Mall Santa Aeshia DeVore Branch ... Bar Girl Stephen O'Neil Martin ... Hector the bartender