bite of the cherry

The phrase originates from the observation that a cherry is a small fruit typically consumed in a single motion. It was initially employed to describe the act of attempting to repeat a task that had already reached its conclusion, a second bite being a logistical impossibility for a fruit of such modest dimensions.

By the 1940s, the term cherry had acquired a colloquial association with virginity. The resulting social awkwardness prompted a shift in American usage toward the word apple. While the first recorded instance of the apple variation appeared in 1922, its adoption proved problematic for the internal logic of the idiom. As an apple requires several bites to consume, the original nuance of a singular, unrepeatable opportunity was largely surrendered to the requirements of decorum.