Sean Sr. copes with ill feelings after being benched on his hockey team right before the South Side Championship game. Meanwhile, Ann has her first session as a psychologist and the family sees more of her mentor, Grace. Sean and Marco deal with their first business failure together, while Bridget thinks about an awkward moment.

Ann discovers a secret that Dan and her mentor, Grace, have been hiding, as Sean Moody Sr. attempts to play matchmaker for Bridget. Meanwhile, Sean Jr. and Marcus make their very first sale.