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I'm a documentary junkie, so not sure if this is popular or not. I've just stumbled across it and found it online back in December.
Travel Bum Show​
Travel Bum Show was created by the photographer Andrew Lindy. Not critically acclaimed, just an average guy from Montreal, that lives in NY.
Long story short he decided to stop working and test the waters of the dating world out. Not just normal dating, but dating different types of woman from France, Germany, Puerto Rico, Cuba, and obviously USA. He documents the girls through "confession cam" (knowingly) and just shows his progress and rejections along the way. Very entertaining imo. As one reviewer put it, "Travel Bum Show is a hit, bc it allows for viewers to live vicariously through Mr. Lindy.

"Quit your job, buy a ticket, get a tan, fall in love, never return."

First two episodes...
New York Episode 1: Anna (10 Minutes)
http://www.travelbumshow.com/travelbum/videos/new-york-episode-1-anna/

New York Episode 2: Pavla (8 Minutes)
 
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