What is "hobo romance"?
It is often used in Cards Against Humanity game online

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Two meanings   will appear.   First,  the Romantic Idea of the "itinerant worker" or "tramp" in American Culture.

http://www.press.uchicago.edu/Misc/Chicago/143783in.html

Another meaning might be something like the Romance between    a homeless man and woman,  or between  people who have no property and no structure in their life.

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I don't know what it means, but knowing something of that game, it's undoubtedly offensive. Maybe ask your question here:  http://boardgamegeek.com/thread/696546/references-you-might-not-have-gotten

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I am not sure what the phrase is supposed to mean, but a Hobo is a homeless person.

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Vagrant dalliance?

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