Alex Riley experiences defining moments at different points in his life.

Young Alex gives away his most prized possession to impress his crush, mid-life Alex struggles to find the money for a trip; older Alex tries to make birthday plans so he won't have to spend it alone.

Midlife Alex is devestated when he learns Ron showed Abby his favorite movie before showing him; young Alex convinces Justin to sneak out of the house to watch, "Star Wars"; older Alex finds himself working for Eleanor at the diner.

Midlife Alex is tempted to find his biological father when he helps his daughter with a family tree project; young Alex must perform at Ron's reunion talent show; older Alex meets older Abby's new boyfriend.

Midlife Alex contemplates leaving his partnership with Darryl; young Alex works with young Darryl on an invention; older Alex meets Eleanor's fiancé.

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

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.