Early thirty-somethings Daniel Bloom and Will Morrison had been best friends since they were children, with Will's wife, Maggie Claire, added to that friendship. Their combined friendship ended five years ago, when Will "disappeared", none of the two hearing from him until now when Will unexpectedly ends up on the lakeside home doorstep of Arthur and Mary Bloom, Daniel's parents, who also have not seen Will since that time, and to who Will does not divulge the reason for his disappearance or return. The only news that Will provides is that he has just finished writing a book which is to be published. Not knowing the issue between the three, the senior Blooms decide to call both Daniel, who is now a New York based magazine writer and one time novelist, and Maggie to come and deal with whatever the reason for their estrangement with Will. Beyond the fact of the aftermath of Will's disappearance for those five years, both Maggie and Daniel are aware of the reason for Will's unilateral decision. In addition, Daniel and Maggie have not seen each other also for the same reason for Will's decision to leave. As the five spend a largely uncomfortable few days together at the lake house, the questions become whether Will, Maggie and Daniel can get over the incident, they can emotionally deal with the reason for the incident, and Maggie can deal with what she felt was Will's desertion of her. Once they find out what's going on, the senior Blooms may be able to provide an interesting perspective on the matter.

Thirtysomething Vincent dreams of winning back his ex, Louise. Grief-stricken and driven to despair, he kisses the break-up goodbye by nocturnal parties and ephemeral affairs--until this day a delivery man gives him a parcel he has never ordered: a strange bottomless box, through which he experiences a time travel that would take him back to standing at Louise's side right before they split up.

Country singer Zane and fiancée Jeannette's wedding is interrupted by the last leg of a contractually obligated tour, leading them on a roundabout journey back to one another. After a video of Zane saving a female fan goes viral, Zane finally becomes the country music superstar he's always dreamed of being. Jeannette is happy and supportive, but after he misses their new wedding date, she begins to worry his dreams may no longer have room for her. Jolene lends her wisdom, but she needs to face up to her own past first. Quinn and Nana Suze share a lesson that sets up a beautiful finish at the wedding - if it ever happens.

Cameron and Wren have had an open marriage for the last 3 years. They set rules as boundaries to assure a healthy open relationship, however they quickly learn that rules applied to the art of emotion will often be broken.

Nicky Beaton and Simone Cole have been best friends since they were children growing up as next door neighbors in the town of Marsden. Despite their geographic distance in Nicky now living in New York City, they will be spending both Thanksgiving and Christmas together on Nicky's return for the respective holidays. Those holidays end up not being as either envisioned. After her first husband Ryan abandoned her and their now fifteen year old son Anthony years ago, flower shop owner Simone will imminently be getting remarried, this time to high school classmate Jeremy Winters. While Simone is bracing herself for the arrival back of who she considers Jeremy's overbearing mother Miriam Winters for the holidays, she is ill-prepared for the feeling she has of being shut out of the bonding that is going on between Jeremy and Anthony, especially in wanting that precious time with her son before he goes away to college in three years. And what Nicky believes will be her short Thanksgiving stay in Marsden ends up being extended to Christmas upon news that her parents, Linda and Dave Beaton, are selling the family home, making this holiday season their last in that house. In helping her mother pack up the house, Nicky discovers among her old high school things a never seen Christmas card that was apparently secretly placed in one of her textbooks. The card is truly a love letter from the unknown writer who didn't sign his name. While Nicky is now a successful businesswoman operating her own consulting firm, she has many insecurities from her high school days, and thus goes on a quest, with help from her parents and Simone, to discover who her high school crush was in needing that affirmation that high school was not all bad. While she is focused on that past, she may miss what is currently right in front of her in the form of Derrick Marshall, her parents' real estate agent who is a bigger part of Nicky's past than she realizes.