Alice asks Ben for an assistant, and he assigns Roman to the job, which leads to Alice and Roman to form an unexpected bond. Crystal arranges a funeral to honor a friend at the Sunshine Center, and Alonzo admits the truth about a past relationship.
Ben teams with Alonzo to play tennis great Jimmy Connors and actor Fred Savage in a celebrity tennis tournament. Ben reveals his past with Alice to Alonzo, and a careless act on Crystal's part inadvertently bring her closer to her son, Roman.
Ben encourages Crystal to get closure with her ex (singer James Taylor) by finding him on their anniversary. While he helps Crystal, Ben asks Roman to entertain his date, the quarterback of a women's lingerie football team. Elsewhere, Alice and Alonzo try to handle two rowdy Internet billionaires.
Ben wants his employees to like him, but his program to make that happen backfires. Meanwhile, Crystal invites Alice and Alonzo on a double date with her new boyfriend, and Ben assigns Heather to find a new halftime entertainer when the arena's mascot quits.
Heather sets Ben up on a blind date with her sister, Stephanie, and it seems like a match made in heaven...at first. And since Roman is too shy to ask Heather out, Ben goes on a group date with Stephanie, Roman and Heather. Meanwhile, Crystal asks Alonzo to put her dog through the paces in a dog show, and Alice tries to impress a visiting friend.
Manager Ben Donovan (Matthew Perry) turns 40 and starts to re-evaluate his life in the pilot of a sitcom that follows the goings-on at a San Diego sports arena. Ben's coworkers include Crystal (Allison Janney), his unpredictable boss; and Alice (Andrea Anders), a friend with benefits.