In recent years, organic single crystals combining elastic and photoluminescent (PL) properties have attracted extensive attention due to their promising applications in many fields. However, elastic organic crystals with two-photon luminescence (2 PL) waveguiding properties are still rarely found, which is imperative for various applications, including near-infrared (NIR) bioimaging and nonlinear optical (NLO) photonic devices. This work reports an elastic single crystal with a long needle shape, anthracene-9,10-dicarbaldehyde (An-DC). Its crystal (100) face exhibits highly reversible bending by applying the mechanical force, which is facilitated by the van der Waals (C– H···π), H-bond (C–H⋯O), and π···π interactions among molecules. The crystal emits a strong orange-red fluorescence when excited by blue-violet light. Interestingly, it also exhibits excellent two-photon fluorescence emission when stimulated by near-infrared light. Based on these linear and nonlinear optical characteristics, the waveguide applications of the An-DC crystal were implemented. Notably, in the bending state, the luminescence performance and the crystal structure of the An-DC crystal are maintained well, which can be used as a low-loss material for linear and nonlinear optical waveguide devices, thus expanding the potential use of flexible organic crystals.