Free spirit Lee Ann plans to sell her baby to pay her rent, much to the dismay of her roommate.

Up in Heaven, the angelic supervisor Gideon sends the apprentice angel Maya down to Earth to earn her wings by sorting out the lives of a group of friends. When Jim learns that his good friend Bill has gone mad and now believes in an invisible talking bear called Oswald, he agrees to bring their group of friends back together for the first time in 12 years for a yacht trip.