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.

Sean Sr. struggles with back pain, so Bridget's old friend, Nick, comes around to help. Ann becomes suspicious about Dan's love life, as he makes an important decision. Meanwhile, Marco and Sean Jr.'s business is growing.

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.