A young lawyer, Jane Liu, is assigned by her mentor to help Madam Wong, a 75 years old repeated shoplifter, as a pro bono defense counsel. What seems to be an easy open and shut case suddenly takes a weird turn when Jane discovers that Madam Wong's repeated petty crimes are intentional and deliberate.

The story of the Lim family from Long Long Time Ago, continues in this two-part film series. Conflict grows between Ah Kun and his nephew Shun Fa. Themes of a generation gap between those born in the 1950s and the following generation are explored in their varying reactions to nation-building policies implemented from the 1980s to the present day.

Evan (played by Shawn Thia) and Sarah (played by Xenia Tan) enlist into the Institute of Sustainable Population, a governmental facility that assigns all conscripts a spouse as a drastic measure to increase the country’s population. They both hope to make the best out of their situations, albeit in polar opposite ways. Evan tries to game the system for his benefit, whereas Sarah works towards an honest living when their paths eventually cross - for the worse.

Ah Huang, Ah Qiang and Ah Hui have been friends for as long as they can remember. When Ah Huang's mounting debts drive him to desperate measures, Ah Qiang and Ah Hui agree to lend him money. He uses the money to build an illegal business. Even after the business become successful, he refuses to repay the money to his friends. However, when the business collapses, Ah Huang is forced to question everything as his family, friendships, and remaining money are all threatened.