Amber Verdon loves the global travel aspect of her job as Project Manager with Chicago-based Marsh Technologies, her work which has led to her putting her first love, painting, on the back-burner, perhaps permanently. Her original career thought was to do that travel while she led the bohemian life of the painter. While mulling over a very attractive offer for a promotion which would give her a more settled life in London, Amber is called back to her small hometown of Whitbrooke Harbor, Illinois by her mother, Barbara Verdon, as her father, Rick Verdon, is currently laid up, and she requires some help for a few days at the family café, despite the culinary arts not being among Amber's skill set. It is an especially busy time in Whitbrooke Harbor with planning for the imminent Founder Days celebrations, this the one-hundredth anniversary, Amber who plans to stay until Founder's Day. While back in Whitbrooke Harbor, Amber learns that the family is facing financial hardship with their rent for the café recently being raised by the new property owner, they unable to make any of their operational payments in the process. Amber also gets involved in the Founder's Day celebration organization herself, she working closely with Jason Taylor, a carpenter by trade, he and his younger sister, Molly Taylor, who works in the café, the last two descendants of the town founders. Jason, who had wanted too to lead the life of the world traveler, long ago returned to Whitbrooke Harbor upon his parents' passing to look after Molly. As Amber and Jason spend more time together, they start to fall for each other. With everything else happening in her life, will Jason be a factor in what Amber decides to do about the London job?

Every 4 years of group of hometown friends get together, catch-up, have a few laughs and take part in a talent show that stems back hundreds of years.

Halley lives with her six year old daughter Moonee in a budget motel along one of the commercial strips catering to the Walt Disney World tourist clientele outside Orlando, Florida. Halley, who survives largely on welfare, has little respect for people, especially those who cross her, it an attitude that she has passed down to Moonee, who curses and gives the finger like her mother. Although the motel's policy is not to allow long term rentals, Bobby, the motel manager, has made arrangements for people like Halley to live there while not undermining the policy as he realizes that many such tenants have no place to go otherwise. Halley, Moonee and Moonee's friends, who live in the motel or others like it along the strip and who she often drags into her disruptive pranks, are often the bane of Bobby's existence, but while dealing with whatever problem arises, Bobby has a soft spot especially for the children and thus, by association, their parents, as he knows that Moonee and others like her are just children acting like a children under whatever guidance they have, Moonee who has less guidance than most. Although there are some lines which he will not tolerate to be crossed, Bobby lets most of the disruptive things that they do go, largely as long as it does not affect the bread and butter of the motel, namely the tourist trade. The summer in this collective is presented, when Moonee and her friends, such as Scooty, are out of school and are left largely to their own devices while self-absorbed Halley does whatever she wants, often just staying in the room watching TV. Halley is supposed to look after Scooty, the son of Halley's friend Ashley, they who live in the unit immediately underneath Halley and Moonee's, while Ashley is at work at a local diner. In turn, Ashley pilfers cooked meals from the diner to feed Halley, Moonee and Scooty. Over the course of the summer, Halley systematically begins to alienate one by one the people who are her unofficial support by responding with that disrespect to anything she feels is against her. As such, Halley begins to take more and more extreme measures to maintain the life she leads with Moonee.

Once one of the biggest musical acts in the world, Bedford and Sullivan - comprised of childhood friends Steve Bedford and Mike Sullivan - broke up ten years ago, an on-stage incident which was the last straw in what was always a somewhat fragile professional relationship. The two have not spoken since in subsequent actions having fractured their relationship even more. While Steve has managed to eke out a solo career with whatever moderate success solely on the strength of goodwill toward the duo, Mike has retreated from the world in those issues that led to that on-stage incident, that is until now as he has agreed to a televised Christmas reunion show called "Bedford and Sullivan at Big Red", Big Red being the Sullivan family home in the small town of Pineville. Talent manager Dianne Carter, who represents neither Bedford or Sullivan but who has some stake in the show, is asked by the show's producer Troy for some assistance, especially in dealing with Mike who is largely missing-in-action regardless of he having agreed to do the show. Of the agents in Dianne's agency, who she assigns to the task is Quinn Allan, for a reason Quinn believed she had kept a secret: that Quinn is Mike Sullivan's daughter, albeit estranged. Quinn, who does not want to deal with her father, is able to negotiate a deal with Dianne in reluctantly accepting this assignment. In heading back to Pineville, Quinn learns that Steve is currently represented by Jason Bedford, Steve's son and Quinn's childhood friend who Quinn believes exacerbated the problems between their respective fathers in the intervening years. In reconnecting with her father, Quinn learns that both he and Steve need this show to happen for different reasons as Quinn, Jason, Steve and Mike negotiate and renegotiate, the latter especially around Bedford and Sullivan performing arguably their biggest hit for the show, One December Night, a very personal song for Mike and one that has some very painful memories. In the process, Quinn and Jason start to fall for each other, a road to a happily ever after for them threatened by what happens with the show.