Clifford Geertz once wrote: “Translation is not a simple recasting of others’ ways of putting things in terms of our own ways of putting them, but displaying the logic of their ways of putting them in the locutions of ours… [it is] catching ‘their’ views in ‘our’ vocabularies” (1983:10). In our digital age, culture is getting both ‘smaller’ and ‘bigger’. It is no longer the big C culture of literature and the arts, or the culture of anthropologists or sociologists, but local ways of life and everyday behaviors, attitudes and beliefs. Paradoxically, culture is also getting bigger, operates on a global scale, connects through the affordance of technology, ‘migrates’ with people on the move and becomes an increasingly denationalized, deterritorialized and decontextualized commodity (Kramsch 1998, 2009, 2014). This paper aims to investigate the challenges involved in trans-lating cultural experience from one language to another in the second/foreign language classroom. I will first review research on the relationship of language and culture in Applied Linguistics. I will then present some of the findings of a recent study by Lihua Zhang and myself of some eighty professional language teachers, both native and non-native, teaching 17 different languages on various campuses of the University of California (Kramsch & Zhang 2018). Their testimonies will lead us to reflect on the nature of the challenges encountered, particularly on the post-modern challenge of teaching across different timescales.