This year, it has been a decade that the concept of click chemistry was pioneered in polymer and material science by the exploration of the synthetic scope of copper-catalyzed azide/alkyne cycloaddition (CuAAC), the click benchmark. The impact on the endeavors of polymer chemists has been substantial because the power of this concept, featuring modularity, orthogonality, and versatility for the design and synthesis of polymeric materials, was recognized very soon in macromolecular research groups worldwide. After this first burst of research activity, challenging the boundaries of CuAAC in terms of attainable polymer constructs, ongoing method development, and implementation, in response to the need for metal-free alternatives, resulted in a valuable toolbox of click-inspired conjugation methods. Because of the large diversity of employable reactions, applied in various polymeric systems, the first-time or occasional click user will be confronted with a burden of choice. Therefore, the principal aim of this Perspective is to clearly denote the recent progress of click-inspired chemistry in macromolecular science by detailed conceptual analysis and to provide some selection procedures, allowing potential users to readily match their expectations of click chemistry to the state-of-the-art. Consequently, first-time or occasional users should be able to identify and select the most appropriate click-inspired reaction for their purposes and eventually contribute to the next generations of advanced polymeric materials.