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The paper presents a model of Schadenfreude, pleasure at another’s misfortune, resulting in a typology of cases of this emotion. Four types are singled out: Compensation, Identification, Aversion, and Injustice Schadenfreude. The typology is first tested on a corpus of 472 comments drawn from three social media, Facebook, Twitter and Instagram. Then a specific corpus of comments is collected and analyzed concerning a specific case of Injustice Schadenfreude, the posts concerning Brexit, United Kingdom leaving the European Union. From the analysis, it emerges that spatial or factual closeness does not look necessary to feel Schadenfreude. Finally, a lexicometric automatic analysis is conducted on the general corpus of Italian comments collected using several hashtags and enriched by comments about the fire of Notre Dame, showing how even complex emotions like Schadenfreude can be automatically extracted from social media.