This account highlights recent contributions from the Lacour group at the interface of chirality and light–matter interactions. Cationic helicenes, ylide-derived macrocycles and heterocycles, and boramidines are presented as complementary chiral platforms for tuning photophysical and chiroptical properties, notably ECD and CPL. Resolution methods and chiral ion pairing further extend these studies to advanced regimes, from supramolecular assemblies to ultrafast and X-ray spectroscopy.