Bet on Me

Bet on Me was a special broadcast pilot where host Casey Jost finds everyday people on the street by giving them a chance to win cash by people watching and then correctly guessing details about the lives of the people around them.

Premise
Jost and his contestants watch passers-by, and procrastinate about their personal lives of these total strangers. After the contestant answer questions like: "Is that guy with his girlfriend or mistress?" or "Has that woman ever smoked marijuana?", Jost stops the strangers to reveal the real answers.

Link
Official Website