Recent scholarship has subjected eighteenth‐century masculine identities to complex and contested analyses, but paid relatively little attention to friendship. The correspondence between Charles Jenkinson and John Robinson, hitherto a resource for high political narrative, is here examined to trace and analyse the development of lifelong sympathy and affection between two diligent, conventionally polite but privately emotional men, whose friendship outlived the chances of patronage and politics that initially threw them together. The evidence sheds light not only on events in high politics but also on the nature and significance of a close relationship between male friends in middle and old age.