We study the emergence of non-Gaussian quantum features in pulsed squeezed light generation with a mesoscopic number (i.e., dozens to hundreds) of pump photons. Due to the strong optical nonlinearities necessarily involved in this regime, squeezing occurs alongside significant pump depletion, compromising the predictions made by conventional semiclassical models for squeezing. Furthermore, nonlinear interactions among multiple frequency modes render the system dynamics exponentially intractable in naïve quantum models, requiring a more sophisticated modeling framework. To this end, we construct a nonlinear Gaussian approximation to the squeezing dynamics, defining a "Gaussian interaction frame" (GIF) in which non-Gaussian quantum dynamics can be isolated and concisely described using a few dominant (i.e., principal) supermodes. Numerical simulations of our model reveal non-Gaussian distortions of squeezing in the mesoscopic regime, largely associated with signal-pump entanglement. We argue that the state of the art in nonlinear nanophotonics is quickly approaching this regime, providing an all-optical platform for experimental studies of the semiclassical-to-quantum transition in a rich paradigm of coherent, multimode nonlinear dynamics. Mesoscopic pulsed squeezing thus provides an intriguing case study of the rapid rise in dynamic complexity associated with semiclassical-to-quantum crossover, which we view as a correlate of the emergence of new information-processing capacities in the quantum regime.