In the series opener, a 14-year-old boy living in Chicago in 1991, was on top of the world inventing cool things and celebrating the Bulls' first championship, until his mom moved him to Los Angeles.
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.
Young Alex gives away his most prized possession in an attempt to impress his crush, Nori.
Mid-life Alex is devastated when he learns Ron showed Abby his favourite movie, 'Star Wars.' for the first time, a moment he had been waiting for. Also, in 1991, Young Alex convinces Justin to sneak out of the house to watch 'Star Wars.'
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.
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.
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.
Young Alex is forced to have a fist fight with Phil Ricozzi, who blames him for breaking up with Nori. This causes midlife Alex and Derryl many problems. Older Alex and Nori attend Phil's funeral, where he realizes what Phil meant to him.
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.
