Art brings rich, pleasurable experiences to our daily lives. However, many theories of art and aesthetics focus on specific strong experiences-in the contexts of museums, galleries, and concert halls and the aesthetic perception of canonized arts-disregarding the impact of daily experiences. Furthermore, pleasure is often treated as a simplistic concept of merely positive affective character, yet recent psychological research has revealed the experience of pleasure is far more complicated. This study explored the nature of pleasure evoked by everyday aesthetic objects. A mixture of statistical and qualitative methods was applied in the analysis of the data collected through a semi-structured online survey (N = 464). The result asserts the experience of emotional ambivalence occurred and was composed of a variety of nuanced emotions and related association, rather than just a combination of contradicting emotions. Such paradoxical pleasure is defined as a self-conscious hedonic exposure to negative emotions in art reception. The study also depicted four types of attitudinal ambivalence: loss, diversity, socio-ideology, and distance, reflecting contextual elements intertwined into experience, and the connection between ambivalence and intense emotional experience.