Okay, here's my story. On my lunchbreak to get some food. A man approached me afterwards and introduced himself and asked if he could sit down. Now, as a veteran of Temple University, I'll tell you that because we are a college located in a major city we have lots of homeless people that come and walk around our campus asking for money. It's a profitable venture for them since we're all niave and theres enough of us on campus that someone has to have change. So anyway, like I said. He sat down and began to talk to me, and I began to talk to him. It was a very nice chat and frankly he was very honest by saying that he wasn't interested in money (I believed him) and he just wanted to talk to someone. I know that people on the street barely get to talk to people, that was one of the things I walked away with from a Midnight Run (wikipedia link). He told me a lot about himself and about his life, and I listened. I was honestly interested because he seemed like he was being very sincere and honest. At some point the topic of walking came up, when I noticed his shoes and feet. I made a very knee jerk reaction and gave him $25 and a subway token and said to him, please, go down and get some sneakers and socks for yourself. It caught him by complete surprise. I was surprised at myself for doing it, but at the same time his feet were absolutely torn apart and how could I worry about $25 dollars that I was going to buy a pair of headphones with, when the guy literally had ratty sneakers without laces and no socks. He never asked for the money, and at many points in the discussion he said that he can't believe that I gave him that much money, and that in addition to the sneakers he was going to find a way to get a set of clothes and a hat. I think he's a really good guy deep down, and just has had some just god awful luck. At some point, the conversation basically came to Is there a way that we can meet again? It's nice to be able to talk to someone, instead of being treated like an animal. I went ahead and told him that I work on campus two days a week (did not say where) but I think I may have made a mistake. I told him where I'm going to be living on campus (building wise) and said that I would keep an eye out for him. Only afterwards I realized to my horror that I've given up too much information and the real nasty part of my personality thinks Great, now he knows that there is one stupid sucker that he can keep getting money from despite the fact that he never asked for money and I gave it to him of my own free will. Needless to say, I was a bit troubled, but felt good about giving him the money because he sounded very honest about getting the shoes and clothes. Until later today. Basically I went down to South Street to spend some free time and on the way back to the subway I was approached by another homeless man, who asked me for money. I had two dollars in my wallet and without thinking just gave it to him. I believe he noticed how I was carrying some cash, and then tried to sell me some weed (probably about as much as the two dollars I gave him was worth) and said Just give me $20 I was like, sorry, I've got to go, and promptly walked away. I was very frustrated with myself when I realized that those two dollars that I gave him were in fact the same two dollars that I needed to purchase my fair on the subway. All my other bills were twenties and I really hate breaking them for subway tokens. Really hate it. I immediately went sour on the whole busniess of helping others and I felt like a big fat dumb hick idiot from the rich white suburbs for giving away my money so freely, and also resented how much of a big ****ING idiot he must have thought I was for trying to sell me a gram of weed for like 100 times what it must have been worth. To make matters worse! I get to the SEPTA trainstation, fumbling with all my stuff to purchase my ticket when AGAIN! I get hit up by a hobo. I TURN AND SEE ITS THE SAME ONE THAT HIT ME UP FOR WEED LITERALLY SIX BLOCKS BACK!!!!! I have no idea how he got there that fast! He beat me and I was using the subway! I missed my train by literally a minute, and ended up sitting on a platform bench stewing over this whole matter. (WHEN YET AGAIN I WAS ASKED BY A FEMAL HOMELESS PERSON IF I COULD SPARE CHANGE!!!! ARRRRRRGH!!!) I know it's not her fault and i'm not going to be like, damn all hobos who dare to ask me for money but I kept on getting reminded of how much of an idiot I felt like after the second homeless person. I decided to write this (I'm riding the 8:40 train back to my home). I'm just really upset about the second hobo trying to sell me the weed, the fact that I gave over my $2 so casually when I really should have used it for MY subway ride (as opposed to the subway ride of the second homeless person I suspect). I know I'm probably overreacting about the $20 bill that I had to break, but it's that and the fact that I met the same guy at the station and he asked me for money AGAIN. I think it feels a little better to vent it out, but I just felt like such a fool, and then in retrospect starting wondering if I had been a sucker to the first guy, and I'm worried that maybe I've made a slight mistake about telling him where I'm going to live this coming year. It's an absolutely huge apartment complex so it's not like he's going to sit on my porch or anything, but I think the worst that could possibly happen is that every time I leave for class he hits me up for money. On the totally opposite hand, I could be the only person in the entire world that that guy knows who actually has talked to him and reaffirmed to him that he is a human being, and is important enough that his opinion carries weight. Not to mention he (hopefully, like I said he promised) got a pair of shoes and socks and a set of clothes out. This coming august, I could be the only person he ever really talks to. The really not so nice part of me just thought about or how I could be the person he stabs one dark night as I walk back to the apartment building for $20 bucks. See what I mean? Help! I need advice, thoughts, anything.