On a flight home to Chicago for a family wedding, childhood friends Josh and Molly innocently agree to fake a wedding engagement to make Josh's dying father happy. Things quickly get out of hand with their two boisterous families, and a series of events causes them to pretend to be a couple and start planning a phony wedding. When the playacting begins to foster real feelings, the two must make some serious decisions: Split up and return to their lives in LA, or make a life as a couple back in Chicago?
Annie's life is a mess. But when she finds out her lifetime best friend is engaged, she simply must serve as Lillian's maid of honor. Though lovelorn and broke, Annie bluffs her way through the expensive and bizarre rituals. With one chance to get it perfect, she’ll show Lillian and her bridesmaids just how far you’ll go for someone you love.
Doug Harris is a loveable but socially awkward groom-to-be with a problem: he has no best man. With less than two weeks to go until he marries the girl of his dreams, Doug is referred to Jimmy Callahan, owner and CEO of Best Man, Inc., a company that provides flattering best men for socially challenged guys in need. What ensues is a hilarious wedding charade as they try to pull off the big con, and an unexpected budding bromance between Doug and his fake
best man Jimmy.