Katie Jolly is a driven young woman with aspirations to leave her small town of Homewood and the family business behind for a career in New York City. Katie’s dreams come to a halt when her father’s sudden injury leaves the future of the company on her shoulders. Saddled with Jolly Lumber’s looming financial troubles, she must also navigate the complexities of love and family as well as the pressure to win the annual Lumberjack Competition.

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.