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.

With Christmas quickly approaching, Sean Sr. receives the top honor as the lector of Midnight Mass. Meanwhile, when Sean Sr. invites some unexpected guests to Christmas Eve dinner, Ann starts to unravel.

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.

In an unexpected turn of events, all the Moodys find themselves living under the same roof again when Bridget, who lives in the Chicago area, returns to her childhood home with a suitcase in hand after a fight with her husband.

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.

Sean Jr. finally agrees to join Sean Sr.’s Moody Heating and AC business, but trouble ensues when a rival company infringes on their territory. Meanwhile, Bridget finds someone in whom to confide, while Dan struggles with the guilt of being interested in cousin Marco’s girlfriend, Cora.

Just when the Moodys think things couldn’t possibly get worse, they are faced with a devastating challenge. All Ann wanted was a nice, white Christmas!

Christmas caroling is a Moody tradition that Sean Sr. does not take lightly. However, when an unexpected guest shows up to the Moody house, caroling takes a hilariously embarrassing turn.

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.

Freshly single, Dan returns to his childhood home for Christmas to find it’s in various stages of disarray, with one functioning bathroom. As the extended family gathers for a welcome meal, Dan meets Cora, with whom he instantly clicks.