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Explanation: I think the translation of this sentence largely depends on the preceding context. I don't know what the context is, but I would like to have a guess. Could "winking and nudging" mean that we wink and nudge each other as we work our way through? My impression is winking and nudging are our action, and don't really refer to the road itself. I think your second translation is quite good.
isahuang Local time: 23:17 Native speaker of: Chinese PRO pts in pair: 491