Ten years after the unexpected and tragic deaths of their parents, siblings Elliott Warden and Emma Hastings enter 1985 in very different places. Emma prospers, a matriarch of a loving family and owner of the successful club Johnny Dubs, but Elliott flounders in a meaningless career and a sea of shallow relationships. The return to Michigan of his high school sweetheart and her best friend, Donna, provides Emma the perfect excuse to intervene in her brother's love life. Her machinations quickly go awry after the arrival of a pretty, young waitress with a heart of gold and a vivacious, talented and beautiful musician with a soon-to-be fiancée. Believing Elliott to be courting romantic disaster with the younger women, Emma makes several risky plays to finally set him on the path to wedded bliss with Donna. A headstrong Elliott, however, has his own ideas. Will he make the right choice or lose them all?