The main purpose of this research paper is to investigate predicates expressing the possessive meaning “to have” in Taiwan Mandarin and Czech. In Taiwan Mandarin, the word you has the semantic meaning of “to have” and “to exist” (Huang, 1987; Her, 1991). Mít in Czech, however, has three main usages (Daneš, 1987; Karlík — Nekula — Rusínová, 1995; 1996; Čechová, 2000; Cvrček, 2010): it is used as a modal, an auxiliary or a possessive verb. According to the language data collected from Taiwanese students who study Czech, these students often use mít in Czech to express not only possession but also existence, or they incorrectly use it as an auxiliary — in other words — their knowledge of you in Taiwan Mandarin seems to interfere (Brown, 2007) with their usage of mít in Czech. In this paper, firstly, relevant literature dealing with the usages of you in Taiwan Mandarin and mít in Czech will be introduced; secondly, there will follow a discussion of the language data collected from the NCCU foreign language learner corpus; thirdly, the grammaticalization theory (Heine, 1997) will be applied to investigate Taiwan Mandarin you and Czech mít, which shall offer a number of explanations regarding the observable typological diversity across these two languages. In spite of the fact that there are similar research papers related to the expression of possessive meaning in these two languages, this paper assumes that the cross-linguistic typological discussion shall bring more insight into the characteristics of these two languages. Furthermore, apart from advancing the typological discussion of these two languages, it is expected that this paper will also aid the preparation of related textbooks and teaching materials.