What's the origin of the phrase 'The apple of my eye'? 'The apple of my eye' is an exceedingly old expression which first appears, in Old English, in a work attributed to King Aelfred (the Great) of Wessex, AD 885, titled Gregory's Pastoral Care. Much later, Shakespeare used the phrase in A Midsummer Night’s Dream, 1600: Flower of this purple dye, Hit with Cupid’s archery, Sink in apple of his eye

The origin of the expression “ apple of my eye ” goes back to the reign of King Aelfred the Great of Wessex in AD 885. The phrase also appears in Old English in “ Gregory’s Pastoral Care .” However, the phrase would stick around for many years before gaining popularity in the early 1600s.