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.

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.

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.

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.

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.

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!

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. 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.