The self-involved head of San Diego sports arena the Sunshine Center, Ben Donovan (Matthew Perry) faces a relationship crisis as he struggles to cope with an unpredictable workplace and even more unpredictable boss, Crystal Cohen (Allison Janney). And as he faces the prospect of losing his "friends with benefits" relationship with his marketing director, Ben learns that Crystal has hired her estranged son as the Center's newest employee.

Expecting recognition on his tenth anniversary at the Sunshine Center, Ben (Matthew Perry) instead finds himself dealing with a difficult teen pop star (guest star Nick Jonas) and a contest that has the staff vying for Crystal's attention. But once it's clear that the rigged contest is really Crystal's (Allison Janney) scheme to get closer to her son, Ben demands acknowledgment for all his hard work, too.

As Crystal (Allison Janney) convinces Alonzo to handle her dog to face off against her arch nemesis Macaulay Ridgeway (guest star Ray Wise) in The San Diego Dog Show, Alice asks for his help impressing a hated high school classmate (guest star Rosa Blasi). And while the spirited competition goes to Alonzo’s head, Heather sets Ben (Matthew Perry) up on a surprise date.

Ben tries to get his employees to like him, but his plan backfires; Heather must find a new halftime act when the Sunshine Center mascot quits.

Already roped into helping Alice face her fears over not being good enough for Alonzo, Ben (Matthew Perry) also takes in Roman after he's been banished from living with his mom. After revealing that her problems with Roman started when her pregnancy derailed a promising figure skating career, Crystal (Allison Janney) finally gets a chance to make things right with an audition for Smurfs on Ice.

When an important audit reveals a sentimental side of Crystal (Allison Janney) he’s never seen before, Ben (Matthew Perry) helps her resolve her lingering feelings for an ex-husband (guest star James Taylor). Alonzo hopes to use a lingerie football game to persuade a pair of dot-com millionaires to donate to a new children’s center, but it’s Alice’s sales wizardry that closes the deal.