So let me try to sum up the past 3 years as quickly as I can without rambling.
We met 3 years ago and instantly clicked as friends. Time passed and I developed a small crush on him, nothing serious though as I knew he had a girlfriend. A few months passed and they broke up, a few weeks after that he asked me out. I told him I didn't want to be his rebound and to give me some time to think things through. About a week later I decided I did like him so I may as well give it a shot. Well I told him I would go out with him if the offer was still on the table he told me, "last night I got set up with a friend of a friend. It went well, and we have a second date planned. I don't want to just throw away a good thing, and also risk our friendship. I like you, but I know we're both kind of unsure." I agreed told him I completely understood and that was that. A few months later he was still with the girl and while in a fight where one of his friends was present his friend had let something along the lines of "you should have gone out with Lilly" slip. This of course didn't make the situation any better. She demanded an explanation bla bla bla she went control freak and refused to let him ever speak to me again. Of course our paths still crossed from time to time at this point though I was over him.
2 years passed, in that time I could count on 1 hand the times our paths crossed, and the words we exchanged. She had gradually pulled him away from ALL of his friends, and they got engaged for reasons that no one understands. Then out of nowhere we crossed paths at a party. We sat and talked a bit, and he seemed miserable they were due to get married within a few months. A week later we bumped into each other and he says, "so I just want to let you know I made a mistake a few years ago and I want to fix it. I've been miserable for a long time and I never should have given you up. After the party I was finally able to admit all of this to myself and realize that I am an idiot. I called off the wedding, and I know things may never be the same between us, but I'd like to hope they could be. Maybe in time they could be better, that is if you'll give me a chance when you're ready, if you ever are. I just thought I should let you know that I'm sorry for everything, especially letting you go. I just hope at the least we can be friends again."
I was essentially speechless and confused. I just looked at him and said, "I'm sorry that things didn't work out for you, but I have to run right now I'm meeting someone," and I ran. Literally.
It's been about a month since then we've talked on and off and bumped into each other through mutual friends that he is reconciling with. Last night at a party he asked me out. I told him to give me time to think about it because I didn't want to be his rebound, and I didn't want to lead him on either because where I am not I don't see him like that anymore.
I've talked to a few of my friends there are those who thought after he asked me out and then started dating her he was a dbag forever. Then there are those who love us both and keep saying, "do it do it!"
Part of me wants to give him a shot, the other part of me says don't do it. So should I or shouldn't I? Before you ask if I'm only considering it because he called the wedding off for me. No, yes it's a romantic gesture to a certain degree, but no. The doubt I have is from being a potential rebound, and already our friendship is pretty rocky I just don't know what to do.