A Jack the Lad - Idioms by The Free Dictionary
a Jack the Lad
Jack the Lad
A confident, carefree young man. Primarily heard in UK. Jim's a bit of a Jack the Lad—he likes his job as a bicycle courier and doesn't care what anybody else thinks.
a ˌJack the ˈLad (British English, slang) a young man who is very confident in a noisy way, and enjoys going out with male friends, drinking alcohol and trying to attract women: He used to be a bit of a Jack the Lad — I never thought he’d settle down and get married.This was originally the nickname of an 18th-century thief called Jack Sheppard.