A well-worn platitude holds that surprise (admiration for the Greeks, but closer to astonishment for their successors) is the starting point of philosophy (while carefully distinguishing philosophical surprise from the routine kind). Surprise also functions as an important concept in aesthetics. Russian formalism elucidates it through the concepts of ostranenie and defamiliarization. Roman Jakobson in 1919 began a heuristically rich analysis that reveals the role of metonymy in prose and new poetry — in contrast to the centrality of metaphor in traditional poetry. This reassessment of the role of contiguity (as well as of randomness and arbitrariness) as opposed to similarity (or, stated another way, syntax vs. paradigmatics) has found some resonance in (mainly, but not exclusively, French) thinking about the concept of event. After its introduction in Gilles Deleuze’s The Logic of Sense (1969), the real apotheosis of the event unfolds among different thinkers (Derrida, Badiou, neo-phenomenologists) who glorify the unexpectedness, unforeseeableness, ineffability and causelessness of the event. The article shows that this kind of event theorizing (with its inherent optimism and joyous enthusiasm for new horizons and possibilities) is bound to the type of event within which that thinking took shape, the “revolution” (as it conceived itself) of May 1968. This “theory” cannot fully account for either certain previous events (the Holocaust) nor subsequent ones (such as 9/11 or the pandemic). Parallel with the thinking about the May 1968 event came reflections on subjectivity, or rather on the rapid alteration in its historical types during the 20th century accompanied by efforts to grasp what has taken the place once occupied by the subject. This new and elusive entity (referred to as advenant or “coming about” by Claude Romano) corresponds to the metonymic, contingent nature of current social and/or semantic reality itself.