Previous studies have attributed little attention to the historical factors surrounding the development of counterfactual meanings in the adverbs almost and nearly, though some have referred to evidence of pleonastic negation found in proximatives across languages. In the present study, the historical development of the two adverbs will be considered in investigating recent data from Late Modern English, in which a majority of counterfactual uses appear with a complement referring to undesirable events, sometimes expressed hyperbolically. It is hypothesised that the presence of intersubjectivity contributed significantly to the development of counterfactual meanings in both adverbs, in focusing attention on the aversion of, rather than the proximity to, the event described in the complement. However, in the case of nearly, the proximative meanings of counterfactuality are likely to have emerged out of contexts in which meanings of temporal proximity (expressing counterfactuality) were ambiguous with meanings of spatial proximity (expressing factuality), as in the frequent appearance of nearly with past participles.