In present-day English, well and now function as pragmatic markers with a wide range of text-structuring and interpersonal meanings. Both markers are used as topic-changers and serve as a means to signal speaker-attitudes or to gain a shared level of understanding between speaker and addressee on the interpersonal level. Whereas well is generally back-looking, now directs the hearer to the upcoming topic (e.g. Aijmer 2002). Because well and now have developed from a similar — adverbial — origin, this paper will examine to what extent the propositional source of the two markers serves a role in their later semantic-pragmatic development. The aim is to examine, by means of a historical corpus study, to what extent the development of well and now has been directed by underlying theories of grammaticalisation — implying semantic bleaching and pragmatic strengthening — and (inter)subjectification (Traugott 1999). Specific attention will be paid to contexts in which speaker and addressee have diverging views and where the use of a pragmatic marker can help in expressing personal stance and in creating interpersonal ties with the addressee. The material for this paper is taken from three historical corpora which contain speech-based data, viz. the diachronic part of the Helsinki Corpus of English Texts (HC), the Corpus of Early English Correspondence (Sampler) (CEECS), and the Corpus of English Dialogues (CED).