According to Jim S7E6 · Ruby's First Date

According to Jim

Season 7 · Episode 6 · Ruby's First Date · 22 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.