This paper investigates the phenomenon of greeting in English, which can be surprisingly challenging for speakers of other languages, such as Chinese. By ‘greeting’ we mean the seemingly ‘simple’ act of choosing conventionalized expressions at the opening of an encounter. Following pilot interviews with Chinese learners of English who reported puzzlement concerning greeting in English, we pursue a two-fold approach to explore conventions of greeting in English and Chinese. First, we use corpora to investigate pragmatic differences and similarities between conventionalized uses of English and Chinese comparable Greet expressions, examining them separately and then conducting a contrastive analysis. This step helps us capture the contextual spread of Greet expressions in English and Chinese. Second, we elicit production data from speakers of English and Chinese to investigate their behaviour in the broader opening phase of an interaction across various contexts. The results of the study help us understand in a differentiated way the puzzlement that certain groups of learners of English feel when it comes to greeting.