I've been keeping an eye out for him. I see him again, and he will receive a half pint.
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He's not panhandleing he's offering a service for money. Made you laugh you pay a dollar. At least there is no 2 drink minimum for his jokes.
Flagging on the corner may constitute an eyesore, but it is free speech. When they cross the line is when they: run at you, crowd you, corner you, put their hands on you, yell profanity, approach after dark, approach near an ATM, follow closely behind you after being asked to leave. I've seen a lot of aggressive panhandling at gas stations, post offices, and laundromats that pretty much constituted assault.
I saw one that said, "I'll bet you a dollar that you'll read this sign." I thought it was clever so I gave him a dollar, which is rare for me. I regularly donate to Denver Rescue Mission because they make sure the homeless eat and they are willing to accept lots of different styles of donations. You can just visit their website and see what they are asking for. That way you know people are being helped and the money isn't going to vodka and cigs.