I often have your way of thinking; it drives me crazy. I wouldn't say I'm in any way a push-over as a result, I'm just a KIND person, to those that seem worth the kindness.

My best mate, some years ago, would pay things (like bus/fuel expenses, when I went to see him, and even food when I stayed) for me, because I couldn't, as I didn't have an income. Anywho, once I started getting an income, I kinda put all that guilt I had for him being such a good friend, and I sorta, ... well, ... bought him a lot. >.< I must've given him a few hundred quid, for things likes games, bus journeys, food, and computer hardware, over the last few years. I did finally stop, when I realised that I had paid him back ages ago. Luckily, he's my best mate for a reason, and as it stands, I don't regret giving him all that stuff, and I do once in a while treat him, but not because I feel an compulsive need to repay him, but because he's my brother and he deserves it, even if he is a pain in the arse, sometimes. xD

Thing is, I usually only spend money on people who're family, or very, very good friends. Be careful, though, ... can be very easy for someone to take advantage of your kindness, so make sure you're being generous to the right person. No harm in being nice in this world, but arseholes don't deserve niceties, IMO.