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Two friends, John (played by Owen Wilson) and Jeremy (Vince Vaughn), crash weddings to pick up women. One day they crash the wedding of the daughter of the Treasury Secretary, Secretary Cleary (Christopher Walken). Instead of short-term flings they end up being invited to the Clearys island estate, and potentially meet the loves of their lives...
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
John Beckwith
Vince Vaughn
Jeremy Grey
Rachel McAdams
Claire Cleary
Christopher Walken
Secretary Cleary
Isla Fisher
Gloria Cleary
Jane Seymour
Kathleen Cleary
Ellen Albertini Dow
Grandma Mary Cleary
Keir O'Donnell
Todd Cleary
Bradley Cooper
Sack Lodge
Ron Canada
Randolph
Henry Gibson
Father O'Neil
Dwight Yoakam
Mr. Kroeger
Rebecca De Mornay
Mrs. Kroeger
David Conrad
Trap
Jennifer Alden
Christina Cleary
Geoff Stults
Craig
James McDonnell
Attorney
Jesse Henecke
Attorney
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