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1.
When partying with a large group of friends, the first person to pass out is presented with the hobo surprise. A used condom in the street is found and the contents of the used condom is squeezed out onto the sleeping person's face. Similar to the dispensing of a go-gurt!!!
Katherine was given a hobo surprise much to the delight of her colleagues.
by HS President March 01, 2010
 
2.
The delightful parcel created when you purchase and eat a packaged lunch (such as fast food take-out), and put all the wrappings, crusts, and other leftovers into the largest package when you are finished, so that a garbage-sifting vagrant may find a delightful meal at a later time.
"McDonalds has the best hamburger clamshells for making hobo surprise!" said Danielle, an avid philanthropist.
by Mad Margaret January 14, 2010
 
3.
When a homeless person enters a phonebox to search for spare change in the coin slot and upon leaving he is surprised to find a bucketful of semen falling onto his head, splattering the exquisite contents all over his rags.
"Peter got hobo surprised last week, and he loved it"
by Horatio Q Nobcluster December 26, 2007