In this talk, I will explore the systemic asymmetry in the use of wh-interrogatives between some European and American dialects of Spanish and Portuguese. In particular, both Caribbean Spanish and Brazilian Portuguese have generalized the use of preposed subject pronouns in these interrogatives (cf. Caribbean Spanish ¿qué tú quieres? ‚what do you want?‘), as well as clefted interrogatives (cf. Brazilian Portuguese que que vocé quer? ‚lit. what that you want?‘). Using both synchronic and diachronic data from these dialects, I investigate the possibility that one or both of these processes can be explained in terms of language contact between earlier dialects of Spanish and Portuguese and Romance-based creoles.