Within the frameworks of both formalist and cognitive-functional linguistics, the form and function of the English (nominal and verbal) gerund have long been studied from a theoretical and univariate perspective. In this retrospective review chapter, we argue that recent usage-based and quantitative methodologies, inspired by Cognitive Linguistics, have led to a myriad of novel insights into gerundive constructions. We show that conceptual features associated with “nominal” or “verbal” construals of an event, as presented in the cognitive-functional paradigm, can be operationalized as variables within a quantitative, variationist approach. In doing so, the variation between nominal and verbal gerunds is assessed from a probabilistic rather than dichotomous point of view, with particular attention to lectal variation and lexical constraints. The picture that emerges is multifactorial and opens up many avenues for future research.