Old friends and Second Chances- ADVICE

I need some advice! 

In high school I knew this boy. We clicked and became super close super quickly. I liked him as a friend, but he liked me as more. We did the whole define-the-relationship thing and j thought we were okay. However, he just couldn't get over his feelings. After about a year or so of trying to work things out and even taking breaks to give him time to move on, he gave me a choice of a) dealing with him pursuing me forever or b) not being friends at all ever. I chose option b because I couldn't deal with him crossing boundaries all the time, nor should I have had to. 

A year later (freshman year of college) the kid contacts me and wants to try being friends again. He told me he had worked through his feelings. I told him we could try, but I made no promises. After about a year, we were closer than ever. I counted him as one of my closest friends I had ever had, which was saying a lot for me (I had abundant trust issues back then). Sophomore year, I go back to school and he asks me to skype. Immediately, I'm freaking out and sure he's going to cut me off again. And that's what he does. He said he had never gotten over his feelings for me and hoped that if he denied it for long enough (that he had feelings) that they would go away. Of course I was hurt and furious. Things ended again. Three weeks later he tries to talent back, but I was still so mad and hurt and upset that I cussed him out and told him to basically go to hell; that he had lost me as I was never coming back. 

I'm now graduated from college and it's been a couple years. Over those years, as much as I have been Andre and resented him, I've missed him. He was one of the best friends I've ever had, even if he kept screwing everything up. We've talked a couple times over the years (mainly one of us would mistakenly text the other), but always incredibly briefly. 

We started talking again today. He's married now and I'm practically engaged. It sounds like he would like to start reconnecting, but I'm hesitant. I still have some resentment towards him, but I've also missed him. I know we'll never be close like that again. It would also be inappropriate if we were. 

Basically, my dilemma is this: should I even give it a chance? Part of me misses our friendship and is curious if we could manage to be friends (all of us including significant others, not just us). But I'm not sure it's a smart idea, you know? I'm the person who always gives too many second chances and I'm not sure I'm seeing this situation clearly. Do you guys have any advice? 

Sorry this post was so long! 😂