A V.F.D. Chaperone is a V.F.D. member who takes a V.F.D. Apprentice in order to teach them everything they need to know about working within V.F.D. There are, at the time of Lemony Snicket's apprenticeship, 52 chaperones of V.F.D. who are ranked on a list for the apprentice to choose from.
V.F.D. Chaperones are volunteers known to train apprentices in the field of their specific area of interest. They are selected by the apprentices, but once they are paired up, the chaperones are given complete control over the apprentices, including dictating where they go and what they do, effectively giving them "In Loco Parentis."
The job of the chaperone is to teach their apprentice in their area of interest, giving them a further education and experience in the occupation they wish to go into. They also seem to train their apprentices in Volunteer experiences, with VFD missions being sometimes assigned to the pair.
Chaperones are often supervised by another Volunteer, whose identity is not revealed to them. The supervisors will assess their teaching and the apprentice's progress, which will eventually be given to the superiors to categorize the chaperones on a ranking list.
It is unknown how one becomes a chaperone, though it is likely considered their occupation within the organization.
- S. Theodora Markson, marked as the fifty-second best chaperone on a list of fifty-two
- Chaperoned Bertrand Baudelaire, graduated before Who Could That Be at This Hour?
- Chaperoned Lemony Snicket, announced his own graduation in Why Is This Night Different from All Other Nights?
- Unnamed Librarian chaperoning Kit Snicket