According to Jim (2001)

S5E4 Charity Begins at Hef's

Cheryl wins a pair of tickets to meet Hugh Hefner at the Playboy Mansion through a charity contest that Jim had secretly signed her up for. Excited about the opportunity, Cheryl chooses to bring Dana along instead of Jim, much to his dismay. As they prepare for their glamorous adventure, Jim grapples with his feelings of jealousy and disappointment, leading to humorous situations as he tries to come to terms with Cheryl's decision.