Charlie Babcock's Homosexual Encounter (S01E09)

Pepper's love life takes a turn when Grady Harper, the renowned and single quarterback from Chicago, enters the scene. They share a delightful dinner together, but their romantic evening is interrupted by Charlie, Grady's number one fan, who suddenly shows up. Charlie quickly realizes that Grady is focusing all his energy on Pepper. This prompts Pepper to question Grady about his sexuality, and both she and Charlie urge him to come out publicly. Meanwhile, Pepper also finds herself at Chick's high school reunion, where she enjoys a live performance by music icon Liz Phair.