<p>The present study explores the lived experience of cycling in four distinct situations using a bicycle simulator and a convergent parallel mixed methods design (<i>n</i> = 33; eye tracking, <i>n</i> = 22; explicitating self-confrontation interviews, <i>n</i> = 8). The design of bicycle infrastructure is influenced by various factors, including land availability and levels of cycling activity in urban areas. These factors result in inevitable interactions between cyclists and other road users, such as motorists and pedestrians. However, the cycling experience in diverse environments involving such interactions is not well understood. The present study examines the emotions (pleasure, arousal, and dominance) experienced by cyclists, in addition to their perceptions, cognitive activities, and actions. The study explores how these contribute to situation preference. Cycling while interacting with other road users affects emotions. In particular, a number of significant differences in pleasure were observed across different situations. Furthermore, a strong positive association was identified between preference and pleasure. Cyclists adopted specific behavioral responses in response to the interaction with other road users. These findings underscore the potential benefits of segregating cyclists from other road users to reduce interactions, enhance safety, and optimize cycling performance.</p>