Introduction The modern world is becoming increasingly more open, which helps to facilitate relations between the nations and even whole civilizations. Today, if a person has a wish and sufficient funds, they can freely and relatively safely travel around the world, study or work in different countries, and explore cultures. However, it was not always the case, and experience in understanding foreign cultures often came by trial and error method, sometimes at the cost of serious risks. Those people had often suffered failures and setbacks on their way, but it would be impossible to establish any sort of communication without their efforts. Tim Clissold and Johnathan D. Spence tell the stories of people who acted as the trailblazers of intercultural dialogue. Their misfortunes can teach the reader that what humanity takes for granted nowadays was non-existent in the 18th century or, in Clissold’s case, just about thirty years ago. Common Themes and Concepts Both Clissold and Spence focus on describing the sheer cultural shock of a person who tries to explore and understand a foreign culture. Both of their protagonists had faced significant, if not impregnable, troubles in their Western-Chinese cultural dialogue. A British investor suffered a heart attack after the years of business activities in China, and a Chinese copyist’s life in France led him into a mental asylum. These troubles can be explained with a classic cultural context approach introduced by Edward T. Hall, which divides national cultures into two categories — high and low context, respectively (as cited in Norhayati, 2016, p. 350). Western European and American cultures are generally considered low context — task-centered, regulated mainly by the written rules and laws, and characterized by shorter interpersonal interactions. On the other hand, Chinese culture belongs to high context cultures, where long-term relations are essential, many rules are not written and require internal knowledge, and strong boundaries divide the representatives from the outsiders. Without proper adaptation to context, protracted cultural interaction can turn into a shocking experience with unpredictable or even undesirable outcomes. Characters of Mr. China and The Question of Hu experienced severe shocks caused by cultural context differences. Clissold remembers his own working experience in China as a business representative who tried to understand local business practices and enter the rapidly growing Chinese market by investing in Chinese companies. Due to existing protectionist restrictions of the Chinese economy, Clissold and his partners could not simply buy out Chinese firms. Instead, they had to buy a share and work together with their new Chinese business partners, which proved to be challenging and stressful. At first, Clissold visited numerous Chinese state officials, who gladly received him and promised to facilitate the deals with local enterprises, but did not act according to their words (Clissold, 2004). The New York bankers, who he managed to persuade into visiting possible investment projects in Shanghai, were so shocked by Chinese enterprises that they aborted their business trip p