I love my boyfriend but I'm not sure if I made the best decision. We have talked it over but this isn't the first time we broke up. I thought maybe we needed a break this time and he was willing to let us take a break. In our relationship we were together almost 24/7. I realized how unhealthy this was. Plus he did not get along that well with some of my friends. In his past as a child, he was always depressed and lost a lot of people.

I didn't want to hurt him, but I felt like we just kept going in circle. I don't think we should continue going out because he keeps asking for another chance and I keep getting confused and changing my mind. Our relationship has been badly damaged already and I honestly don't think our relationship will be the same if we went out again. I wanted take time to heal these wounds and he said he could wait as long as I needed, but I don't think it's fair for the both of us.

What if I heal but move on and he's still waiting? This good-bye was really painful for the both of us. Did I make best decision though?

You are not sure of things and it sounds like you don't really want to be with him. So yes you made the right decision.
Goodbyes are painful but when you are not making it as a couple there is no point in being miserable.

Having read your post,it sounds like you've already answered the question.I think you have made the right decision as you say you kept going round in circles,breaking up ,getting back together, breaking up again etc.etc.

If for some unknown reason later down the road you do end up back together, then just call it fate,but for now I think you both need to go your own ways.

I am sure he will not be waiting for ever and will move on himself,you both need to experience other parts of life to grow.I'm not sure how long you have been together but you will miss each other,especially if you've been together 24/7,but it will get better as time goes on.