Abstract Two bis(3‐pyridyl) ligands 1 and 2 based on a planar chiral [2.2]paracyclophane scaffold were synthesized in enantiomerically pure forms. These ligands act as trans‐chelating ligands for square‐planar‐coordinated metal centres such as palladium(II) ions. Upon forming mononuclear homochiral [ML2] complexes, they show complete chiral self‐sorting in a narcissistic self‐recognition manner as proven by NMR spectroscopy, mass spectrometry and single‐crystal X‐ray diffraction.