According to Jim - Ruby's First Date

Seizoen: 7 - Aflevering: 6 / 152 - Eerst uitgezonden: 29 januari 2008 - Episode ID: 5762

While Cheryl is still out of town, Jim is having hard time dealing with Ruby's girl problems, so he assigns Dana to help her. However, when Dana tells Ruby to go out on a date with an older guy, Jim if forced to intervene, as he, Dana and Andy end up following Ruby to her date.