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Beat the bum to the punch with "Hey buddy, can you spare a dollar? Got any extra smokes? I just need a dollar to get on the bus."
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At one point of my life when I was younger I got so sick of bums asking me for money I started doing this. I would see them make eye contact start to ask.. and then I would say "hey/ do you have any spare change???"
Usually about 1 out of 3 would give me some spare change and want to talk about this and that.
So it back fired on me, lol I hated taking grubby coins from hands that have not been washed in days... lol