After a brief reconciliation, Dan and Cora break up again, sending him back home to his parents' house. Ann then forces Dan into an unwanted therapy session with her friend, Grace.

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 Sr. reconsiders his retirement plans, while Ann has second thoughts about her career. Meanwhile, Dan and Cora bump into each other again, Sean Jr. gets serious about his future and Bridget's relationship with Nick gets complicated.

Ann has no intention of leaving her new psychology practice, and Sean Jr. continues to brew up schemes to get rich quick.

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.

The Moody family gathers once again for a wedding when something sudden shocks the entire family. Meanwhile, Sean Jr. and Marco make amends and things turn around for Bridget's love life.

The Moodys picks up with Sean Sr. contemplating retirement – road trips across the country in an RV with Ann, while Sean Jr. takes over the family HVAC business.