I saw a homeless guy do this recently. Even though I was driving a car at 30 miles an hour exiting the freeway, it was clear he was using the age old tactic of “building a personal connection, through stimulating conversation on a topic of mutual interest.” It just goes to show confidence, and charisma aren’t directly related to financial or physical well-being. The question remains, aren’t all homeless people technically coworkers. If they break up panhandling under that overpass is going to get awkward. Is it ever appropriate to do this kind of thing at work?