Feeding the "Homeless"

I did something kind of stupid yesterday. I fed a homeless guy.

Actually, he probably wasn't even homeless. He wore cheap dirty clothes, but he probably has a place to live. He was standing on the corner by my neighborhood Starbucks. As I passed he asked, "Could I have a dollar? I'm just trying to get something to eat." As someone who has occasionally given money to "beggars" and immediately regretted it, I instead offered to purchase him some food.

"If you prefer that, sure." OK, I said, and as he followed me he asked, "Is it OK if we go to Quizno's?" As that's where I was going myself, I said that was fine. After I ordered my sandwich, I told the lady to get the guy whatever he wanted. He then asked me if it was OK if he got a Combo. I was a little irritated that he was taking advantage of my generosity. But.... I had offered. And really, at this point, what was a couple more dollars? So I paid for his sandwich plus a drink and whatever else he got. He thanked me several times and I was relieved that he never said "God Bless You"...

I did all this, and quite frankly, I felt like a bit of a chump afterward. Why did I buy this particular guy a sandwich? People ask me for change or a dollar every day and I usually pass them by. But this guy had a specific request for food. Other times, when I've made the offer to purchase food for someone, they backpedal and say they need the money for the bus or other random things. But this guy took me up. Maybe he was truly looking for money to buy food. But he wasn't starving. He was by no means skinny. Frankly, he was rather obese. But that doesn't mean he couldn't use the nutrients.

I've never been starving, but I've gone without eating because I couldn't afford to eat. I've had times where I almost passed out because I was trying to stretch my groceries by eating less. But when it's gotten truly desperate, I've been lucky to have people who could help. So I'm sympathetic. 

And yet, I still feel like I was a fool, like this guy took advantage of me. This isn't directly related to religion or the normal topics of this blog, but it still sort of feels like a moral-ish question. What do you think?