Flow around a cylinder is a classical problem in fluid dynamics and also one of the benchmarks for testing viscoelastic flows. The problem is of wide relevance to understanding many microscale industrial and biological processes and applications, such as porous media and mucociliary flows. In recent years, we have developed model microfluidic geometries consisting of very slender cylinders fabricated in glass by selective laser-induced etching. The cylinder radius is small compared with the channel width, which allows the effects of the stagnation points in the flow to dominate over the effects of squeezing between the cylinder and the channel walls. Furthermore, the cylinders are contained in high aspect ratio microchannels that render the flow field approximately two-dimensional (2D) and therefore conveniently permit comparison between experiments and 2D numerical simulations. A number of different viscoelastic fluids including wormlike micellar and various polymer solutions have been tested in our devices. Of particular interest to us has been the occurrence of a striking, steady-in-time, flow asymmetry that occurs for certain non-Newtonian fluids when the dimensionless Weissenberg number (quantifying the importance of elastic over viscous forces in the flow) increases above a critical value. In this perspective review, we present a summary of our key findings related to this novel flow instability and present our current understanding of the mechanism for its onset and growth. We believe that the same fundamental mechanism may also underlie some important non-Newtonian phenomena observed in viscoelastic flows around particles, drops, and bubbles, or through geometries composed of multiple bifurcation points such as cylinder arrays and other porous media. Knowledge of the instability we discuss will be important to consider in the design of optimally functional lab-on-a-chip devices in which viscoelastic fluids are to be used.