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In the last decades, the quantity of information produced and distributed due todigital resources has been growing; big data is contributing to a better perceptionof our cities. The aim of this paper is to understand spatial segregation in the cityof São Paulo (a city known by its social inequality and urban poverty) byscraping social media tags of emotions. We compared aspects that suggestsocio-spatial inequalities: urban poor versus feelings of love and hate, versusfeelings of joy and fear and the social vulnerability index as background. Threeissues are considered in this research: the emergence of urban space big data,digital inclusion, and architects and urbanists' access to big data. To unveilurban poor singularities through social media is an opportunity to reconnectcommunities to urban design.