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.