Everyone views singlehood differently. For Edrick (Elvin Ng) , it is the pain of not being able to find the right girl. As for his brother, Wesley (Nat Ho) , it signifies a life of freedom. Yet for Edrick's best friend Jess (Felicia Chin), she simply blames her old-fashioned mother, who forced her to focus on her studies instead.
Having a matriarchal Peranakan grandmother, getting married and having children are non-negotiable, and she threatens to leave the brothers out of her will unless they do so. Unfortunately for them, Edrick has been single for too long, and has little interest in the fairer sex, while Wesley has been engaged to his partner, Olivia (Ching Shu Yi), for so long and yet never marry. When they are about to in 20 days, Olivia realizes Wesley has been cheating on her. The trio embarks on their 20 days journey, each learning and going through their own troubles in singlehood. Will Edrick and Jess find their own share of love in 20 days? Or will Wesley's marriage plans fall through due to the ongoing affair? And will their grandmother's wish ever be fulfilled?