Nathan tries to date his mother's dentist in secret after Carol adds her to the Miller Family Blacklist for charging her a $75 cancellation fee for being late to her appointment. Meanwhile, Carol goes to great lengths to get her money back, and Tom can't figure out why he keeps waking up with gum stuck in his hair.

When Tom proudly tells the family he's dating a much younger woman, Nathan goes undercover to spy on him and make sure his father isn't being scammed by a gold digger.