Structured personal accounts of contemporary events and happenings composed in the Irish language are exceedingly rare in the pre-Revival period; that is to say, in the period prior to the founding of the Gaelic League or Conradh na Gaeilge in Dublin in 1893. The first such composition and the main focus of this paper is the account of the Ulster Earls’ journey from Rathmullan in Co. Donegal to Rome in 1607–8. It was written by Tadhg Ó Cianáin, a member of the native learned class, who accompanied the Earls on their journey. Tadhg Ó Cianáin’s account of the Earls’ journey to Rome includes many instances where specific reference is made to conversation as an accomplishment and pleasurable social activity. There would seem to be no doubt but that this reflects Ó Cianáin’s observation of a practice which was being cultivated on the Continent for societal and aesthetic purposes, and regarded as being conducive to family, kindred and community cohesion. Nonetheless, the examples of conversation-in-being culled from Irish literature more generally and cited in this article bear witness to the ongoing engagement with conversation, discourse and storytelling which has always permeated Irish culture.