Jim prepares Kyle for his first "date" with Ruby's slightly older piano teacher, Mandy, whom Andy has fallen for and is secretly dating behind Kyle's back.

Cheryl and her friends, eager to get an afternoon away from the kids, arrange a "Daddy and Me" group for Jim and other dads with young kids at their home. Jim makes the best of a potentially boring situation by turning babysitting into a sporting event--staging baby races where the dads bet on their kids and drink beer.