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1.
A homeless version of a bobo. Bobo is French for bourgeois-boheme--in other words a hippie yuppie. Those young folk who simultaneously proscribe to hippie ideals and tastes while valuing a yuppie lifestyle. The hobobo adds lack of permanent residence in the mix and implies vagabond status.
Hey Sandy, did I tell you about my most recent trip to Thailand? I met so many hobobos! They all were wearing fisherman pants and playing on their ipads.
by hobobo4life June 20, 2011
 
2.
Someone who is a double hobo.
Look at that hobobo!
by TheWiggidy April 03, 2004