Situated within the variationist sociolinguistic framework, this study has focused on the qualitative analysis of structures in Brazilian Portuguese (BP) that resemble other syntactic phenomena, such as preposition stranding in English and orphaning in French — i.e., respectively, “é algo que vale a pena conversar sobre” and “e se quiser dormir, tem três quartos a casa, pode escolher qualquer um para”. Based on a corpus of Tweets extracted and compiled through R, we examined a sample of twenty thousand Tweets in order to identify the potential envelope(s) of variation. In other words, this sample provided data to also explore when the stranded variant could have occurred but did not and when it could not have happened without loss of semantic equivalence between sentences. Thus, this has allowed us to evaluate which factors regulate the use of the stranded variant in comparison with other strategies. The partial results of this research suggest that there are two envelopes of variation: one with four relativization strategies and, in constructions different from relative clauses, another in which there are only two variants besides the phrase-final preposition one. Regarding relative clauses, the following are the three other relativization strategies: the standard variant (“é algo sobre o que vale a pena conversar”), the resumptive pronoun variant (“é algo que vale a pena conversar sobre isso”) and the prepositional phrase-chopping variant (“é algo que vale a pena conversar”). Although there is the issue of data scarcity when analyzing this type of syntactic phenomena, our findings suggest that sentences with the stranded preposition “sobre” are more frequent and acceptable than others with “com”, “de”, or “para”. There is also a hypothesis of common ground being one of the determining factors for the possibility of phrase-final prepositions occurring in BP. Finally, this study aims to contribute to a broader discussion of syntactic variation, which is still a very controversial topic within Variationist Sociolinguistics.