In this talk, I will discuss progress in our understanding of Legendrian surfaces. First, I will present a new construction of Legendrian surfaces and a direct description for their moduli space of microlocal sheaves. This Legendrian invariant will connect to classical incidence problems in algebraic geometry and the study of flag varieties, which we will study in detail. There will be several examples during the talk and, in the end, I will indicate the relation of this theory to the study of framed local systems on a surface. This talk is based on my work with E. Zaslow.