Until she was engaged, however much an upper class woman might resent her chaperon, there was no honest way to escape her. Even after her engagement, the only man she could be around alone that was not a relative was her fiancé, and even then only for limited periods of time.

Because chaperons were so common, no one thought it odd to have one present. A gathering of wealthy young women could easily have as many chaperons present as there were girls. These women were a constant presence and a part of everyday life.

When a couple did become engaged they had more freedom, but were still expected to stay strictly within the realms of propriety. The fiancé usually took the chaperon's place, making sure his future bride's honor was still protected.

The only appropriate way to escape from a chaperon was to become engaged, at which point a lady's honor was given into the care of her fiancé. Even then, an honorable man would take great care to make sure that his future bride's honor was cared for and not attempt to seduce her or in any other way take advantage of what privacy their engagement offered. He would also never break the engagement, as the time his fiancé had spent alone with him would then damage or even ruin her reputation, even though she would still be a virgin.

Less honestly, a young woman might evade a chaperon who was not as watchful as she should be. While most young woman would not do so no matter how a chaperon grated, it was possible to slip out of sight of a distracted or otherwise occupied chaperon. It would likely be more common for a child to escape her watcher than a woman who had come out into society, because it would tarnish her reputation less than it would for a courtable woman to do so.