To investigate six shy and five non–shy individuals' experiences of shyness and descriptions of behaviors, emotions, and thoughts in social situations, a semi–structured interview guide was employed. The interview guide included questions about situations that induce shyness as well as descriptions of the participants' shyness from the time when they started to feel shy until the present. Also, the participants were asked about the possible impact of shyness on their social and academic life, as well as possible strategies they use to overcome shyness. Questions about negative and positive consequences of shyness were posed. The participants were also asked how they view other shy people. The analysis was based on interpretative phenomenological analysis (IPA; Smith, Jarman, and Osborn, 1999). The main results showed that the shy participants started to become shy during junior high school, at which time the non–shy participants gradually became less shy. On the other hand, the shy participants remained shy throughout high school and in most cases beyond that time. The results further showed that shy and non–shy participants could be quite passive in new, social situations. However, shy individuals were concerned about what other people think, whereas non–shy individuals focused on the environment in order to grasp the social rules. One finding unique to shy individuals was that some of them experienced identity confusion associated with their shyness. Since these participants are adults it cannot be explained by adolescent identity-formation. The present findings also suggested that shy individuals feel shy in spontaneous situations, whereas non–shy participants feel shy in non–spontaneous situations. Furthermore, the results indicated that the shy participants used strategies involving role play. This finding suggests it might be difficult to determine whether someone is shy or not. Further, the present results indicate that self–ratings are valid on their own, and that peer ratings may actually fall short.