Jim still struggles with household duties while Cheryl is out of town, but has real problems when Ruby asks to go shopping for a training bra. Jim asks Dana to be the temporary mom for shopping. Turns out, Ruby is getting ready for a date.
- Ruby wants to go out on a date, but Jim thinks that she is too young. Since Cheryl is still out of town Jim recruits Dana to back him up, but she thinks that its a good idea and says Ruby can go on the date. Jim still isn't completely happy, but eventually comes around and lets Ruby go. But when it turns out that Ruby's date is an extremely older boy Andy, Dana, Jim, and Cheryl (who is viewing events from a laptop) follow Ruby to make sure she isn't doing anything bad. As soon as Cheryl announces that she thinks Ruby's date is some kid who hit on her a while back Jim decides to go in, but not before he can get his hands on a clever disguise...