Winnie, a dating blogger who anonymously writes under the pen name Luckless, goes viral for a post about a disastrous date with Holden, a perpetually single sports agent who refuses to settle. When Winnie’s boss offers her very own column on the popular lifestyle site, Mush, Winnie has no choice but to keep dating Holden for content. But things get complicated when feelings develop and Winnie learns that Holden has a teenage son.

Allie (Rebecca Dalton), an out of work art teacher, has to accept a job with the Santa Squad to help wealthy widower Gordon (Aaron Ashmore) and his two precious daughters rediscover the magic of Christmas. As Allie is lifting the holiday spirits of the family with Christmas decorations, cookies and shopping, her kindness is rewarded with the most unexpected of gifts: love!

While stuck in her car after an accident, a young woman makes an emergency call and reaches an operator who attempts to keep her calm. Having immediately formed an undeniable bond, they spend months trying to reconnect amongst repeated obstacles and misunderstandings.