When Cheryl wins two tickets to visit Hugh Hefner at the Playboy Mansion in a charity-raising contest that Jim secretly entered her in, she decides to take Dana instead of him.

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According to Jim Season 5

# Title Air Date
According to Jim
5:1 Foul Ball Sep 20, 2005
5:2 The Tale of the Tape: Part One Sep 27, 2005
5:3 The Tale of the Tape: Part Two Sep 27, 2005
5:4 Charity Begins at Hef's Oct 4, 2005
5:5 The Race Oct 11, 2005
5:6 Anec-Dont's Oct 18, 2005
5:7 The Chick Whisperer Nov 1, 2005
5:8 James & the Annoying Peach Nov 8, 2005
5:9 The Dream Nov 15, 2005
5:10 Lean on Me Nov 29, 2005
5:11 The Gift of Maggie Dec 13, 2005
5:12 Sex Ed Jan 10, 2006
5:13 Renewing Vows Jan 24, 2006
5:14 The Stick Feb 7, 2006
5:15 Mr. Right Feb 7, 2006
5:16 Get Your Freak On Feb 21, 2006
5:17 The Grumpy Guy Feb 28, 2006
5:18 Polite Jim Mar 7, 2006
5:19 Daddy Dearest Mar 7, 2006
5:20 The Thing Green Line Mar 14, 2006
5:21 Jim's Best Friend Mar 21, 2006
5:22 Belaboring the Point May 2, 2006

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