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.
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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.
The chaos created by a broken air conditioner and a disgruntled mascot reveals how little respect the Sunshine Center's staff has for Ben (Mathew Perry) – and just how little he knows about them. As Ben is forced to reach out his disgruntled employees, Crystal's (Allison Janney) request for a double date puts Alonzo (James Lesure) and Alice (Andrea Anders) in an awkward spot.
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.
Though Alonzo hopes to use a lingerie football game to persuade a pair of dot-com millionaires to donate to a new children's center, it's Alice's sales wizardry that closes the deal. And 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).
On the eve of a charity tennis event, using Twitter while driving makes Crystal (Allison Janney) a hazard behind the wheel. After her carelessness disables both Alonzo’s tennis partner and Roman, Crystal worries she’ll be sued. And as Crystal looks to avoid legal trouble, Ben (Matthew Perry) and Alice conspire to keep Alonzo in the dark about their past. Guest starring Jimmy Connors and Fred Savage.
As Roman receives an unlikely promotion, a confusing email has Ben wondering if his office romance with Alice is really over. While the ensuing confusion reveals that Alonzo is keeping a secret about his ex-wife (guest star Nadege August), Crystal orders Ben (Matthew Perry) to fire their unpredictable P.A. announcer (guest star Richard Kind). Meanwhile, after the Sunshine Center’s cleaning woman dies, Crystal offers to arrange the memorial service.
Ben’s (Matthew Perry) latest one-night stand becomes complicated when he discovers that Vivian (guest star Lizzy Caplan) is Crystal’s new assistant. And as Crystal (Allison Janney) forgets a promise she made to Roman after she fall in love with a 50-year-old BMX rider (guest star Toby Huss), the Sunshine Center mascot’s need for a new office tests the limits of Alonzo’s kindness.