The story centers around John Beckwith (Owen Wilson) and Jeremy Grey (Vince Vaughn) as they spend the wedding "season" showing up at various weddings to pick up women. A lovely vixen named Claire Cleary (Rachel McAdams) captures the love of John and neither knows how to deal with it. Claire is the daughter of the Secretary of Treasury, William Cleary (Christopher Walken) who suspects something is amiss with John and Jeremy and puts the two up to numerous tasks to prove themselves. Jeremy tries desperately to rein his friend back into the life of a wedding crasher but is met with stiff competition from her family and friends.