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.
During a business trip, event planner Kayley and sports agent Brett find themselves unable to fly home for Christmas due to a snowstorm. Determined to get back to NYC by Christmas Eve, the two team up and try to make their own way home.
Christmas enthusiast Steph, has created a program, Six Degrees of Santa. When Steph's own gift lands in the hands of a leading internet entrepreneur, Jason, he's convinced that the original Santa might be his soul mate.
