According to Jim

Ruby's First Date

Aired Jan 29, 2008 · 9:00 PM ET · 25 min

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.