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.

When Cheryl returns home for a visit the kids end up occupying her time, so Jim decides to prepare a special date with her at the airport lounge, only to end up mistakenly arrested.