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When Cheryl and Dana's mother, Maggie, visits for the holidays, Jim and Cheryl compete with Ryan and Dana for her affection
Cheryl encourages Jim to meet a former girlfriend wants to discuss business for lunch, and then regrets it when she becomes convinced that the old flame has romantic intentions.
When Jim and Cheryl watch an sex education video that is shown at Ruby's school, Jim realizes that he is watching a young him.