Taking E. M. Forster and Virginia Woolf as case studies, this chapter examines the relationships – both clear and opaque – among their lives, their writings, and social progress. From a bird’s-eye view, these interrelations seem clear and linear: sexual tolerance and freedom have expanded since Bloomsbury’s time, signal forms of progress to which these authors’ unconventional loves and sensitive writings contributed. But seen from more intimate angles, these interrelations betray lacunae and discontinuities worthy of modernism. Their lives and writings were often not in sync: they wrote about things they had not experienced (Forster on sexual intimacy), feared things that did not befall them (Woolf foreseeing marriage as a catastrophe), avoided taboo topics (Forster on homosexuality), or failed – due to their lack of vocabulary – to describe avant-garde lifestyles they were enjoying (Woolf on urban tribes, Forster on polyamory). For all their articulateness, it would require later generations, including Bloomsbury’s respondents such as Angelica Bell and Michael Cunningham, to clarify how Woolf and Forster contributed – for good or ill – to the ever-evolving phenomena of intimacy.