John and Jeremy, single in their mid-30s, mediate divorces in D.C.; their summer social life consists of crashing weddings (always with a back story) to meet young women for a one-night stand. As John thinks about growing up, Jeremy convinces him to go to one more, for the daughter of the Treasury Secretary. Each catches the eye of a daughter of the host. Jeremy scores with Gloria, who proves to be a psycho clinger; John wants real romance with Claire, but she has a boyfriend, a privileged hound. Can John convince Jeremy to stick around long enough so he can woo Claire, and can he tell her the truth about himself before she finds out from someone else? What if he messes up?
Owen Wilson, Vince Vaughn, Christopher Walken, Rachel McAdams, Isla Fisher, Jane Seymour, Ellen Albertini Dow, Kieran O'Donnell, Bradley Cooper, Ron Canada, Henry Gibson, Dwight Yoakam, Rebecca De Mornay, David Conrad, Jenny Alden, Geoff Stults, James McDonnell, Jesse Henecke, Lou Cutell, Sparkle, Frankie Ray Perelli, Patricia Place, Chao-Li Chi, Norma Michaels, Ivana Bozilovic, Camille Anderson, Diora Baird, Ned Schmidtke, Jennifer Massey, Larry Joe Campbell, Irene Roseen, Jules Mandel, Betsy Ames, Carson Elrod, Charles Kahlenberg, Kathryn Joosten, Melanie Hawkins, Summer Altice, Lisa Beach, Al Cerullo, Rachel Sterling, Keir O'Donnell, Noel De Souza