This dissertation explores the dialogue between Dream of the Red Chamber (Hongloumeng 紅樓夢, Story of the Stone 石頭記) and Tang 唐 poetry, especially the works of Li He 李賀, Li Shangyin 李商隱, and Wen Tingyun 溫庭筠. Analytical tools and philosophical concepts are developed for approaching Hongloumeng as a deeply intertextual, highly symbolic novel, the specificity of its referential landscape being assessed and clarified. The works of these poets are explored in their capacity as classical inspiration for Hongloumeng’s remarkable, in some ways radical vision of alternative spaces where sexuality, gender, art, and identity can be explored freely and openly. It will be demonstrated how Hongloumeng engages with these poets’ works especially in terms of their critique of existing social hierarchies and of the dismal opportunities afforded for artistic and gender expression. The recurrence of gendered labor in the Tang poetic material that Hongloumeng references is treated with a view toward value production and social reproduction as historical phenomena. To develop an analytical framework capable of representing subtly transforming historical conceptions of dreams, desire, and identity, this work critically engages with notions of serendipity, chance, fate, and morality in Hongloumeng and Tang poetry, while reflexively developing new conceptions of artistic serendipity that can capture how meaning and non-meaning interact, and how dreams and desire interweave. In the process, this work attempts to articulate its theoretical and methodological positionality vis-à-vis Freudian psychoanalysis, the structuralism of Claude Lévi-Strauss, the post-structuralism of Julia Kristeva’s intertextuality, and liminality studies.