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Dictionary.com renders "work both sides of the street" as:

To take two contrary positions at once; have it both ways

Similarly, idiom.thefreedictionary.com has "work both sides of the street" as:

Engage in double dealing, be duplicitous

On the other hand, Urbandictionary.com renders the similar idiom to "walk both sides of the street" as:

Country slang for a bisexual

Is the differentition between working and walking accepted? Compare (http://www.patheos.com/blogs/thoughtfulpastor/2013/06/13/more-on-the-epic-battle-between-good-and-evil/?repeat=w3tc)

Severus Snape–a man who had to walk on both sides of the street.

In short, does walking both sides of the street necessarily carry sexual connotations?

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  • 2
    Personally, I am not familiar with the phrase "walking both sides of the street," but I can see why some people think it has a sexual connotation, just as "his door swings both ways" manages to communicate a similar thought. Commented Aug 22, 2016 at 15:37
  • I've heard both uses, and both used to describe sexual and non-sexual ideas.
    – user191580
    Commented Aug 22, 2016 at 15:44
  • 4
    An entry in Urban Dictionary simply tells you that at some point a single person decided to put an entry in for a word or phrase. They might be the only person in the world for whom the word or phrase has that specific meaning. You shouldn't take it too seriously. Commented Aug 22, 2016 at 15:44
  • As other moderators here have argued, sometimes these social/collective web sites have merit if they might not be correct.
    – user191580
    Commented Aug 22, 2016 at 15:46
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    Euphemisms are very flexible. If you're in a context where someone's sexuality is being described, practically any phrase that involves two-sidedness will be understood to mean bisexual. We don't need set phrases (although some become popular), any metaphor will work.
    – Barmar
    Commented Aug 24, 2016 at 21:55

1 Answer 1

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No, neither of the phrases is necessarily sexual.

For example a 04 April 1906 conversation in the US House Committee on Coinage, Weights and Measures was:

Mr. Wood: The English system is taught in German schools?
Mr. Monaghan: Yes, sir.
Mr. Gaines: Why?
Mr. Monaghan: For the purpose of giving them the advantage of what others have.
Mr. Gaines: Working both sides of the street ?

And 25 April 1955 in the US Senate Mr. Fulbright said this about Time Magazine:

Time accuses me of walking both sides of the street successfully, of conforming to my constituents, and of knowing how to tip my hat to southern industrialists.

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