Tori (Kim Chiu), a hardworking executive assistant, is asked by her boss and childhood best friend Chloe to help her with her playboy ex-boyfriend, Zach (Xian Lim). Tori’s task – date Zach, who’s still hung up on Tori, to prevent him from ruining her present relationship with Greg. Tori pursues Zach but gets embarrassed when Zach laughs at her. Zach realizes that his “relationship” with Tori can be a way to get closer to Chloe and get her back. He then tells Tori that he now agrees to be her boyfriend but Tori’s offer no longer stands. Zach doesn’t want to give up. Tori tells him that the only way that she can be her boyfriend is for Zach to court her. Zach agrees but unbeknownst to him, Tori plans to make him suffer. As Tori and Zach keep up their pretense, they learn more about themselves and discover that they are falling in love for real. But Chloe realizes that she is still in love with Zach and tells Tori she wants Zach back. Will Tori choose her friendship with Chloe over Zach’s love? Will her relationship with Zach be worth risking her friendship and her heart for?