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According to Jim Season 1 Episode 7

When Andy decides Dana is responsible for his inferiority complex, he asks her to join him in his therapy – but she falls for his therapist. Jim and Cheryl disagree about letting the kids to have their own TV; Jim admits to riding his motorcycle, breaking a promise he’d made to Cheryl earlier; and Ruby innocently divulges a secret of Cheryl’s, exposing a broken promise of hers to Jim.

Episode Title: Cheryl's Old Flame

Air Date: 2001-11-14