i never , ever give beggars money. Last $$ I put in a cup was for a high school football team.
Except once. I was at a train station and some guy came up to me in US Army BDUs, said he was just discharged and told me he needed train a couple bucks fare to get to somewhere for something. I thought "this seems unusual, just left the army but doesn't have any money at all? But I don't want to be wrong about this". So I gave the guy $10. If he was lying, he gets points for effort and originality. If he was telling the truth I'm glad I helped him get where he was going with enough left over for a coke and some chips. That's the most I ever gave someone who randomly asked me for money.