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I came across this expression "sneak around with someone". What does it mean? Does it have to do with "date someone"?

Here is an example:

  • We all know that John has been sneaking around with Jenny for five years now.
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  • yes, they have been secretely dating. – anouk Jan 16 '20 at 20:59
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"To sneak around with someone" means to be dating with some amount of (and motivation for) secrecy. It might be an extramarital affair, or a relationship of which some others might disapprove.

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