Since the handover of Hong Kong from Britain to China in 1997, there has been underlying tension and many outbreaks of civil disobedience in Hong Kong. The Hong Kong people’s hostility towards China was fully visualized in the student-led “Umbrella Revolution” in September 2014. This paper explores the roots of conflicts this social uproar from cultural and political perspectives. It examines the fundamental flaws of “One country, two systems” that provokes fear of re-colonization by assessing the similarities between the British hegemony and Chinese sovereignty in Hong Kong. This paper also analyzes the rhetoric of the Hong Kong Federation of Students and their demands, in order to provide a deeper investigation into why Hong Kong people often alienate themselves from their mainland counterparts. One hypothesis in this paper suggests that over a century of British colonization influenced the political ideals in Hong Kong, while such concepts cause resentment as they deviate from those of the rest of China. Seeing the divergence of Hong Kong’s individualism from Chinese Confucianism, this paper proposes that the departure of cultural identities within one national framework creates difficulties for forming a cordial relationship between Hong Kong and mainland China. While Confucianism emphasizes on constructing harmony in the society, the construction itself requires much exclusion, as well as sacrifice of personal interests. This harmony building agenda proves extremely hard in Hong Kong, where multiple languages are spoken and individuality, as opposed to conformity, is celebrated. Despite the return of sovereignty, conflicts between Hong Kong and China become almost inevitable with these fundamental differences.