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.

Avery, a socialite on the path to follow in her powerful political family’s footsteps, is harboring a secret dream to be a fashion designer and work for Lisette Monique. When notorious upper east side player Oliver offers Avery the chance to work for Lisette in exchange for publicly dating him in order to rehab his bad boy so he can keep his trust fund, Avery must choose between her family’s expectations and risking it all to be a designer.