Ion-pairing is a fundamental phenomenon that significantly influences phase-transfer catalysis. In this study, we conduct a comprehensive investigation of ion-pair interactions, aiming to establish a comprehensive understanding of their nature and implications. The study begins with the examination of polar ionic compounds to define the concept of an ion-pair in the context of phase-transfer catalysis. Subsequently, a diverse range of ion-pair catalyst models were explored to gain insight into the factors governing their interactions. Finally, the focus shifts towards the characterisation of real phase-transfer catalysts, bridging the gap between theoretical models and practical applications. Through a combination of computational approaches and theoretical analysis, this work provides valuable insight into the nature of ion-pair interactions within phase-transfer catalysis fields.