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Social and cultural diversity are globally increasing at an unprecedented pace. The implications of this increase for individuals and societies can vary: Benefits such as cognitive flexibility and creativity may ensue when groups manage to cooperate and integrate, but stress and conflict may follow when groups are segregated and marginalised. This thesis focuses on a form of diversity that challenges traditional stereotypes (e.g., a female entering a male-dominated profession) and is thus termed counter-stereotypical diversity. The aim is to empirically and theoretically explore how people psychologically adapt to counter-stereotypical diversity. One primary prediction was derived from the literature, which is that exposure to exemplars of counter-stereotypical diversity (termed counter-stereotypes, CSTs) can boost cognitive flexibility, and this was tested across 12 experiments (reported in Chapters 4, 5, and 6). Various secondary predictions were also tested, for example the role of need for cognition in moderating the effects of exposure to CSTs on cognitive reflection (Chapter 5), and the longitudinal effects of exposure to CSTs on cognitive flexibility and intergroup bias (Chapter 6). CSTs were conceptualised as a special case of expectancy violations, and Chapter 7 theorised that they can be followed by three types of responses: (1) indifference, (2) threat (and defensiveness), and/or (3) challenge (and open-mindedness). Overall, this thesis improves our understanding of how people psychologically adapt to counter-stereotypical diversity.