According to Jim: Ruby's First Date

After Cheryl leaves town to take care of her mom, Jim realizes he can't be both mother and father to his children, so when Ruby tries to have girl talk with her dad, he reassigns "mommy power" to Aunt Dana. But when Dana gives Ruby permission to go out with an older boy, an upset Jim can't stand idly by, and he, Dana and Andy end up following Ruby on her date to the mall.