What happens when nation-builders in an independent state imagine themselves to have fallen behind kinfolk living under imperial oppression, and how does this affect their vision of a future of national unity? This paper explores the shapes that critical self-comparison could take among Romanians in the Kingdom of Romania around the turn of the twentieth century by considering three interconnected vignettes. First, it outlines the context in which politicized notions of mutual interdependence between the Kingdom and Transylvania allowed for comparison as self-criticism to take root and gain salience in the public sphere. It explores the implications that comparison as self-criticism had on ascribing agency and apportioning blame for causes of the disparity between state and kinfolk. Second, it examines two Transylvanian travelogues produced by major political and cultural figures on the fringes of the Romanian establishment, and, in a reflexive move, contrasts their politics of comparison. Third, it offers a grassroots perspective on how the travelogues of teachers and priests, as rank-and-file nation-builders, expressed these topoi. The article contributes to the nascent trend of considering historical comparisons in actors’ own terms, and as historical processes unto themselves.