Think I should help him, need advice...

There is one friend of mine who is talking to this girl and recently he told m he was eventually going to ask her out.

He's a nice guy and from the way I see it he's somewhat of the ladies man, but he has extremly low self esteem and always talks down about himself, at least when its just us two. Also he is still not over his last relationship, he always says how perfect his ex was and how he hates himself that they aren't together, he loathes her.

The girl is the most two faced person I ever saw, she NEVER talks when the whole gang is hanging out she only smiles when someone says a funny joke. And when one of her friends are over she is a maniac she's talking yelling, playfully wrestling and the whole 9 yards. She is also extremly manipulative and does nothing for nobody she gets everybody to do things for her and me and another guy feel she only hangs with us is to meet our othr guy friends.

I don't want him to hurt himself or screw things up, I don't think his is over his ex at all and just wants to date this girl just because not because he "loves her." Do you think I should let them be together or not???

Stay out of it. It's not like he's going to marry her.

Well how can he love her if they don't start dating? That takes a little time for it to develop, at least maturely.

Being a low self esteem guy myself, if you are really concerned about him, you should just talk to him. Let him know that he cannot be happy with somebody else unless he is happy with himself. He may still have feelings for his ex and he will always be looking back a little bit until the next one comes along. Sometimes even after. By all means, help him the best you can to understand that the past is past, he cannot change that. But he can be a better person for the next girl and this girl if he likes her. He can make it much better than the hurt he was feeling before.

Does he know why the last relationship failed and what part he played? He hates himself, loathes her, but what has he learned? Anything? If not, he will make the same mistakes in this relationship as well if he decides to pursue it. Hopefully that's not the case.

Most people need to learn through experience. I'm sure even with a chat he is going to do what he wants anyway. At least you tried and if you say "I told you so" after, it will have more of an impact.

i think he should make his own experience.. if she is the wrong girl for him he will realize that very soon..
dont worry too much about it... :)

As much as it will suck to watch, I'd step back and let him do his thing. He may be offended and think you feel he's "too fragile" to handle this girl and that might be another blow to his already low self esteem. They sound like oil and water anyway, their personalities. The real her will rear its ugly head for him eventually.

Some guys/girls feel the best way to get over someone is to get under someone, literally. Maybe he needs a new piece of @ss to get his mind off the ex.