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.

Charlie is an artist in a slump. He is constantly harassed by his "step-father-in-law," Bob Masters, about his having shot a burglar in the recent past. When Charlie and Jennifer decide to take in Tina as a boarder she turns out to be a model ready and willing to pose for Charlie.