How do I pursue a relationship with him, and risk our friendship?

Life envolves taking risks… sometimes they turn out very good, other times very bad… it’s nothing you’ll ever be able to know before hand. Sure you can have a feeling that it might not work out, or a feeling that it will work out, but if you got the feeling that it’ll work out, you’re afraid that it’s a naive thought and that your own feelings are betraying you.

If you’re afraid it won’t work out, try to keep the end as mutual as possible, so you and him will be able to stay friends without it feeling too awkward. I won’t say I think you should grap the oppotunity and take a chance by asking him out, cause you should decide that for yourself and not for what other think you should… But I’d like to point out that if you don’t try n’ take chances sometimes, then one day you might regret that you didn’t took the chance… and if it was a mistake, then hey you’ll have had that experience and you’ll learn from it till next time, and so will he.

There are probably not many who really wish to admit that their worst relationship wasn’t wasted… many probably would say that their worst girlfriend or boyfriend was not worth even 5 minutes… but I don’t believe that is true, cause everybody becomes more aware of things next time they enter a new relationship. So don’t be scared about it if you should decide to try and get together with him. Should you break up and you want him back, then work for it… get him interested in you again.

If you really feel it could ruin your friendship and it won’t be worth it, then don’t do anything. Just listen to your own feelings what you burn for the most :)

hope you will be happy nomatter what you decide