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1.
Originated on Haight Street in San Francisco. There are so many homeless and street people there begging for money, beer, and left over food, that when a normal person who is dressed well, buzzed and going out for a good time is accosted by one of them (thereby killing your buzz) the non-homeless person may ask in an annoyed fashion “Why do you gotta be so homeless ALL THE TIME??!!!”. It is important to add “all the time” because they continue to be homeless and annoying every time you return to Haight Street.

This phrase can be extended to any situation in which another person is being incessantly annoying or pestering you for the same thing, ALL THE TIME!
Example #1 You are walking down Haight Street and you see a man with a “why lie I need a beer sign” and he accosts you and asks for your change. You say “Man, you are here every day asking for beer money, you should get a job! Why do you have to be so homeless ALL THE TIME???

Example #2
Person 1: Dude, can I borrow $10 dollars?
Person 2: Dude! You ask me for money every time I see you, why do you gotta be so homeless all the time?!
by justaperson888 August 02, 2010