In summer 2006, twenty-year-old Gerald Yeung and his childhood friends from Hong Kong travel to South America and Africa on their parents’ dime. Confronted by challenges foreign to their privileged upbringing, the “Wannabe Backpackers” persevere in their Christian Dior clothes. They make plans to do it again when they turn thirty. The decade that follows doesn’t go exactly to plan. Gerald chases the American Dream in a town of twenty thousand and subzero winters. Others pursue a fast-and-furious life in Hong Kong. They all experience failed relationships, career setbacks, and a decreasing ability to impress girls at clubs.