Hi Reface,
This is going to sound a bit extreme, maybe. But here goes. I believe in order to make good friends you have to be ruthless. What I mean by this is you have to be willing to disregard the people who make you feel bad. I think one of the biggest problems in society is that people settle for second hand happiness - Living through other people, living by an image, living to please others, stuff like that.
Theres no shame in being ruthless where your friendships are concerned. I don't mean be rude to everyone you don't like! But by all means, feel and know the difference between an aquatence and a friend. Also one of the hardest things to overcome with low self esteem is slipping into bad habits, setting yourself up for a downfall. If you're a people pleaser, it's that guilt you have to work on! If your worse fears come true and people don't want to spend time with you, stuff them, you didn't need those individuals in your life to begin with. Just be ruthless and move on to the next bunch of people, and the next etc. Make your motto in this goal "if someone makes you feel bad, get rid of them" Good luck, keep us posted. :)