Trama

Circumstances conspire to keep apart a young woman and her childhood sweetheart, whom she first met during her family's annual Christmas visit to Hawaii.

Olivia and Jeff met at Hawaii every Christmas growing up. In their teens their friendship was on the verge of developing into something else when Jeff's mother died and his family stopped coming. Olivia's family has kept the Christmas-in-Hawaii tradition going, though. One Christmas Olivia, now a up-and-coming architect, suddenly meets Jeff again. He, his sister, and their dad have decided to revive the tradition. Jeff is processing a divorce and they find that the spark is still there but circumstances pull them apart again. What will next Christmas bring?—Devnull

Olivia is the architect responsible for the modern and somewhat boring new city office building in Cincinnati. Apparently the model shown in an early scene means the building isn't finished. The building is being celebrated at the Christmas party, but Olivia has someplace more important to be.

For at least 20 years, Olivia and her family, who live in California, have been going to the same Hawaii resort for Christmas. In flashbacks the viewer learns that about 20 years earlier, Olivia's family met Jeff's family, who have a successful business in Boston. Olivia and Jeff quickly became friends. Both families continued to spend the holiday at the same place year after year, and eventually Olivia and Jeff became more than just friends. But one year, the Williams family didn't come.

A few years later, Olivia looks up and sees a man who looks familiar. Then her family discovers the Williams family has returned, minus Jeff's mother. And Jeff was married, but his wife really wanted to spend the holidays where there was snow, with her family in Vermont. Jeff also had a daughter Madelyn. Olivia is disappointed with this news, but she is happy to see her friend again. There is trouble with Jeff's marriage, which gives Olivia and Jeff's father hope.

Meanwhile, the widowed father Alec begins to take an interest in the pretty manager of the resort, who has welcomed the two families for many years but now has this greater role. This is despite her being the worst thing a Red Sox fan can imagine: a Yankees fan. Jeff's sister is determined to keep her father healthy but he takes every opportunity to cheat. Olivia's brother Todd is with a man and they have a son Ian.

The next year, Jeff returns with Madelyn, and the little girl and Olivia hit it off right away. Jeff is divorced; he moved to San Diego and began selling boats, but his ex likes being up north. Now it's Olivia who is with someone; Gregg didn't come. Yet. But it later becomes clear that while Olivia loves the beach and relaxing, Gregg is very driven and hates a lot of things Olivia likes. He tries hard. Really. And he's a nice enough guy. But the audience wants Olivia to end up with Jeff. So does his dad Alec. Olivia hasn't figured this out yet. Will she? What if it's too late? And what about the other potential romance?