In 1991, 14-year-old Alex Riley's mom moved them to Los Angeles to marry a pilot. In 2017 40-year-old Alex is an inventor/entrepreneur on top of the world until his wife leaves him and threatens to take their daughter with her. In 2042 at 65, Alex is a highly successful businessman who, after suffering a minor heart attack, decides he’s ready to reinvent himself once again.

Darryl encourages mid-life Alex to get back into the dating scene following his divorce. Young Alex has trouble making friends after his embarrassing moment at the school dance. Older Alex finally has his first date with Eleanor.