meanings of ‘up in Annie’s room’

late 1910s: an answer to an enquiry as to the whereabouts of someone who cannot be found—1930s: the space at the top of the dartboard where scores are doubled

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meanings of ‘Tom Tiddler’s ground’

a game in which the player who has the role of Tom Tiddler defends his territory against the others, who try to steal his money—hence a source of easy money

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