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A [metaphorical] town that is said to be visited when one encounters a circumstance/makes a decision that is likely to end in pain and suffering for one or more parties. Often used as a threat ("[I'll take you on] a trip to trouble town buddy") or in relation to a [prospective] partner ("she'll take you to trouble town and give you a first class tour") often used with the terms "trouble city" or "trouble village" depending on the level of trouble given in deemed situation
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