Ruby, an aspiring romance novelist, joins a writers retreat in Tahoe, in order to win a lucrative book deal. But when Woody, the hotel owner, shows her the beauty of nature, Ruby wonders if she's been writing the wrong kinds of stories.

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.