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.

Young Alex gives away his most prized possession, a signed Michael Jordan rookie card, in an attempt to impress his crush, Nori. Also, mid-life Alex struggles to find the money to take his daughter, Abby, on a glamping trip with her friends, and older Alex tries to make plans for his birthday so he doesn’t have to spend it alone.

When Mid-life Alex helps his daughter, Abby, with a family tree project, he's tempted to find his biological father. Also, Young Alex must perform at Ron's family reunion talent show, and Older Alex meets Older Abby's new boyfriend.

Mid-life Alex contemplates accepting a new job offer and leaving his partnership with Darryl. Also, Young Alex works with Young Darryl on an invention for his school’s Invention Convention, and Older Alex meets Eleanor’s fiancé, a contractor helping to fix his roof.

Mid-life Alex becomes friends with another dad at Abby’s school, Ben, without realizing he’s the guy who ruined his marriage. Also, Young Alex competes for Nori’s attention on a field trip, and Older Alex runs into his former business rival, Kelly Frasier.

Young Alex and Justin panic when they are left home alone for the first time and think someone is breaking in. Mid-life Justin notices Mid-life Alex financially struggling and asks for his help with a business proposition. Older Alex and Justin become emotional when they return home to sell their parents' house.

Darryl and Wendy set up Mid-life Alex on a blind date during Thanksgiving dinner. Young Alex and Justin compete to impress Nori's brother, and Older Alex goes to the diner to see Eleanor on Thanksgiving Day and is surprised when Kelly shows up.

Lisa decides to invest money in Mid-life Alex's new invention, and it begins to affect their dating relationship. Young Alex and Justin secretly open their Christmas presents before the holiday, and they accidentally break it. Older Alex interferes with Abby's career.

Mid-life Alex sells one of his inventions to his childhood arch-nemesis, Phil. Also, Young Alex is challenged to a fight by his classmate, Phil, and Older Alex accompanies Eleanor to Phil's funeral and gives an eulogy when no one steps up to speak.

Darryl asks Mid-life Alex to wait until after Wendy's birthday to break up with Lisa. Also, Young Alex runs for student council president against Nori, and Older Alex gets upset when he finds out Abby quit her job.

Midlife Alex contemplates getting back together with his ex-wife when she visits for Abby's birthday party; young Alex invites his lab partner to a dance to get over his crush on Nori; older Alex tries to keep Eleanor from leaving with her fiance.