We predict that the radiative heat-transfer rate between a cylinder and a perforated surface depends nonmonotonically on their separation. This anomalous behavior, which arises due to near-field effects, is explained using a heuristic model based on the interaction of a dipole with a plate. We show that nonmonotonicity depends not only on geometry and temperature but also on material dispersion—for micron and submicron objects, nonmonotonicity is present in polar dielectrics but absent in metals with small skin depths.