Cassie has settled into Middleton and is busy making a home of Grey House. Her boyfriend, Sheriff Jake Russell, and his kids are happy to have Cassie in the neighborhood, but she has yet to gain the trust of some people in town.
A fresh layer of snow covers the ground around Sam’s new lake house. Trudging through the snow, Sam and Cassie walk back to the house after a brisk hike in the wilderness. The scene is a vivid reminder of Sam’s childhood vacations in Montana. As they enter the house Cassie’s eyes are immediately drawn to a group of paint swatches hung on the wall. Sam explains that he always likes to start fresh when he moves into a new space. Sam then asks Cassie about her thoughts on John’s offer to join him on the dig in the Maldives. Cassie knows that the job is a great opportunity for adventure and she is seriously considering the opportunity. Silence follows and as they stare at each other, Cassie tries to break the tension by talking about Sam’s paint swatches. With his eyes still fixed on Cassie, Sam pulls her to him and kisses her deeply. The kiss stuns Cassie and she can only muster a nervous smile.
When Matt Kell, husband and father to two young boys, succumbs to terminal cancer on Christmas day 2005, his widow, Gina (Lacey Chabert) is left to cope with the pain of his loss. Wanting to be close to her kids, Gina starts to volunteer at their elementary school and meets the Spehn children, Jack, Danny and Charlotte. In a tragic coincidence, just weeks after Matt’s death, the Spehns' mom, Cathy, was also suddenly taken by cancer, leaving her distraught husband, Michael (Warren Christie), to care for their three kids on his own. Sensing the hopelessness in Michael that she so recently saw in herself, Gina reaches out to him and his kids and the two families begin to forge an unlikely friendship.
