The riskiest I've ever given was for this guy to streak for a block downtown in college.
It was late at night, about 1 AM, and stores were closed, but the street was still brightly lit and there was some traffic...not on the street itself, but you could see the cars at the next intersection. He ran down the block really quickly and ducked into an alley, I met him there with his clothes. Looking back, it was insanely risky and we got very lucky we didn't get caught, but it was still an awesome night!
Riskiest done was just mooning people in the other dorm at college, nothing special.
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