When sisters Helena and Rachel are fed up with their love and work life, they agree to swap homes for 2 weeks to take a break. Yet what starts out as a relaxing holiday grows into a whole new perspective on their careers, life and most importantly, romance.
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.
When Josh gets the opportunity of a lifetime to audition for Rainbow Puppy’s Broadway musical, Josh and Blue skidoo to NYC for the very first time where they meet new friends and discover the magic of music, dance, and following one’s dreams.