The near-field characteristics of single, double, and arrays of connected dipole nano-antennas coupled to bolometers were studied by infrared scattering scanning near-field optical microscopy (s-SNOM) and analyzed by numerical simulations. Results were consistent with classical antenna theory showing the expected p phase difference across the terminals of the dipoles. However, according to the observed differences between the measurements and simulations, the symmetry of the amplitude signal appeared to be sensitive with respect to the position of the bolometric element relative to the dipoles. The effect of the position of the bolometer on the associated near-field distribution suggests an influence on the coupling and efficiency of energy transfer into these detectors, which could be important for determining tolerances in the fabrication of such devices. These results show how near-field measurements in general can provide critical information to guide the design of nano-antennas, nano-antenna-phased arrays, and integrated photonic devices.