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In this context a "sport" is a young man out and about attending parties, sporting events, charming the ladies and a snappy dresser. In short a playboy bon vivant. The dirt road portion places said sport in an isolated rural area. The connotation of the saying is that he is probably not as "sporty" as he thinks due to the isolated area in which he lives

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Q: What does colloquialism dirt road sport mean?
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