Usually means: Confident, carefree, and sometimes reckless.
Definitions Related words Mentions
We found 11 dictionaries that define the word Jack the lad:

General (8 matching dictionaries)
  1. Jack the Lad: Oxford Learner's Dictionaries
  2. Jack-the-lad, Jack-the-lad: Collins English Dictionary
  3. Jack the Lad, Jack the lad: Cambridge Advanced Learner's Dictionary
  4. Jack the lad: Wiktionary
  5. Jack The Lad, Jack the Lad: Wikipedia, the Free Encyclopedia
  6. Jack-the-lad: TheFreeDictionary.com
  7. jack the lad: Longman Dictionary of Contemporary English

Slang (3 matching dictionaries)
  1. jack the lad, jack the lad: Green’s Dictionary of Slang
  2. Jack-the-lad: English slang and colloquialisms used in the United Kingdom
  3. Jack The Lad: Urban Dictionary

Definitions from Wiktionary (Jack the lad)

noun:  (British, slang) An irresponsible young man, seeking personal pleasure and gratification without any regard to responsibilities. A rogue.

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