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A ten pint challenge would be a person that you are instructed by your companions to woo on finishing your tenth pint of an evening (be that of beer, cider, wine, absinthe, etc. the important part is that it contains alcohol). Such a person would usually be assumed to be quite a minger as it is [understood] you were 10 pints down and thus bear little [responsibility] for your actions. Attempting to successfully charm the pants of someone after 10 swift pints is quite a challenge - although in addition your response to the command is indicative of your [inebriation].
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