The pyridyl group has been extensively employed to direct transition-metal-catalyzed C−H activation reactions in the past half-century. The typical cyclic transition states involved in these cyclometalation processes have only enabled the activation of ortho-C−H bonds. Here, we report that pyridine is adapted to direct meta-C−H activation of benzyl and phenyl ethyl alcohols through engineering the distance and geometry of a directing template. This template takes advantage of a stronger σ-coordinating pyridine to recruit Pd catalysts to the desired site for functionalization. The Ushaped structure accommodates the otherwise highly strained cyclophane-like transition state. This development illustrates the potential of achieving site selectivity in C−H activation via the recognition of distal and geometric relationship between existing functional groups and multiple C−H bonds in organic molecules.