Matthew McConaughey as Connor Mead

Jennifer Garner as Jenny Perotti

Michael Douglas as Uncle Wayne

Breckin Meyer as Paul

Lacey Chabert as Sandra

Robert Forster as Sergeant Volkom

Anne Archer as Vonda Volkom

Emma Stone as Allison Vandermeersh

Daniel Sunjata as Brad

Noureen DeWulf as Melanie

Rachel Boston as Deena the Bridesmaid

Camille Guaty as Donna the Bridesmaid

Amanda Walsh as Denice the Bridesmaid

Emily Baldoni as Nadja

Catherine Haena Kim as Charlece

Noa Tishby as Kiki

Christina Milian as Kalia

Rachelle Wood as Brunette Lingerie Model

Erin Wyatt as Blonde Lingerie Model

Stephanie Oum as Kako

Micah Sherman as Groomsman #1

Albert M. Chan as Groomsman #2

Michael Anastasia as Groomsman #3

Paul Cassell as Wedding Guest Jeff

Dan Whelton as Foyer Bartender

Devin Brochu as Young Connor

Kasey Russell as Young Jenny

Scott Powers as Connor's Dad

Heather Wilde as Connor's Mom

Michael R. Pouliot as Parents' Funeral Priest

Logan Miller as Teenage Connor

Christa B. Allen as Teenage Jenny

Chad Mountain as D.J.

Samantha Rose Goober as Jenny's Friend Marissa

Alyssa McCourt as Jenny's Friend Clarissa

Sam Byrne as Pete Hastings

Gina Gesamondo as Ice Cold Blonde

Toni Saladna as Slapping Brunette

Abigail Kuklis as Blonde Club Model

Paula Merritt as Brunette Club Model

Kortney Adams as Jenny's Colleague

Cindy Lentol as Amy the Stewardess

Kimberly Carvalho as Bar Twin

Ashley Carvalho as Bar Twin

Tina Casciani as Vargas Girl (uncredited)

Quiana Grant as "On Your Car" Bar Woman

Annalaina Marks as Vargas Girl (uncredited)