This article offers a cognitive perspective on the evolution of the semantics of English nominal gerunds (NG) (I regret the signing of the contract) and verbal gerunds (VG) (I regret signing the contract). While the formal differences between NGs and VGs are well documented, their semantics remains largely unexplored territory. The perspective that is taken here is centered on the linguistic notion of reference and various aspects of the conceptualization involved in it. As they formally hover between more nominal and more clause-like internal properties, gerunds form an interesting test case for the cognitive perspective on referentiality. Our corpus analysis describes how the situations that NGs and VGs refer to are conceptualized as deictic expressions grounded in the speech event in Present-day English, and how this has changed since the Early Modern period. It is shown that only a multi-layered model of referentiality can account for the subtle differences found between NGs and VGs: while no fundamental shifts are found with regard to the traditional referential subtypes (specific, non-specific, generic), NGs and VGs do turn out to differ in their choice for either nominal or clausal grounding mechanisms, in their status as existentially stable or flexible entities and in the mental spaces in which they situate the events that they conceptualize.