The 1960s in Czechoslovakia witnessed a remarkable political movement to foster what was then called “socialism with a human face” by merging the egalitarian-distributive vision of socialism with quasi-Western democratic values. This article investigates the social and emotional origins of Czechoslovak reformism and argues that the movement was rooted in the intersection between social class discontent and the collective emotional pain of a revolutionary intelligentsia that I call the “red-collars.” In doing this, the article explores how the post-revolutionary class structure and shared “melancholic” feelings of the red-collars (a mix of discontent with their material/social circumstances and regret for their part in Stalinist revolutionary excesses) shaped their ideological transformation from Stalinism to democratic socialism between 1948 and 1968. Throughout the 1960s, by declaring emotional pain over their past Stalinism, the red-collars voiced their desire to reform the system and reclaim what they considered the “humanistic core of socialism.”