According to Jim S07E06 - Ruby's First Date

Episode Overview

With Cheryl away, Jim struggles to navigate Ruby's teenage dilemmas, prompting him to enlist Dana's assistance. When Dana suggests that Ruby should go on a date with an older guy, Jim feels compelled to step in. He, along with Dana and Andy, ends up tailing Ruby to ensure everything goes smoothly on her date, leading to unexpected and humorous situations as they try to protect her from potential pitfalls.

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