Ahmet Hamdi Tanpınar and his short stories and novels have been one of the main fields of study among researchers of Turkish Literature. Translation studies researchers have also studied his works. Especially his masterpiece, Saatleri Ayarlama Enstitüsü, which was translated into 25 different languages, is among the works examined by translations studies researchers. What makes this novel so popular is the fact that the protagonists in the novel lived in three different periods, namely the First Constitutional Era, the Second Constitutional Era and the Republican Period, and thus remained between the old and the new, the Orient and the West, in other words got confused between traditional and modern cultures. Thus, in Tanpınar’s works, particularly in this novel, which depicts Turkey’s transition to modernism and the social problems experienced in this process, reader encounters culture specific items of the beginning of the 20th century such as Ottoman institutions, religious authorities, religious rules, currencies, and food varieties. Some of these culture specific items are limited only to that period, and some of them can only be correctly perceived within the context of the novel. In this study, challenges encountered by three different translators while transferring these culture specific items of the previous century into different target languages, namely German, Arabic and English and translation strategies that differ depending on the target languages were examined with reference to the cultural affinity and distance in translation. The analysis, conducted within the framework of approaches on translation of culture specific items suggested by Venuti, Newmark, Aixela, and Florin, differs from similar ones as it is carried out on three different target languages and cultures. The challenges encountered in the translation of culture specific items, which are called “realia” (Florin 1993), into a culturally distant language (i.e., German, English) are different from the challenges in cases in which target language is a culturally close one (i.e., Arabic). While the problems that can be encountered when translating into a culturally distant language have been the subject of many studies, it can be said that the problems encountered when there is not enough distance between the source and target culture have been neglected. However, when source culture and target culture are close, other challenges await the translator. An example to these challenges can be implicit reception traps, called false friends. From this perspective, in this study, it is claimed through representative examples that target language to which culture specific items are translated into is of great importance, and that paratexts written by translators also differ in this sense, and whether the target language plays a significant role in the translation process.