A dating blogger who writes under the pen name Luckless, goes viral for a post about a bad date with a single sports agent. When Winnie's boss offers her, her own column, she has no choice but to keep dating him for content.
Avery is harboring a secret dream to be a fashion designer and work for Lisette Monique. 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 image.