When Jeremiah returns home for the first time in years to play a gig with his band, he is recruited to take over as the minister of music for the annual Christmas Jubilee at his home church reigniting the feud, and romance, between the pastor's daughter Willow.

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.