I need advice

Sorry to sound rude but seriously, if what you say about his tendencies are true, then man up and take charge. Yes, he's your friend, but what's the point in giving up if you know the girl you like probably isn't going to get treated well.

There are points where you should consider the standpoints of your friends because they're people you put your trust in, however, when it comes to a serious relationship with true feelings to a girl then he's an opponent. If you like this girl as much as you say, make it known, challenge him and fight for that girl. He'll either give up if he isn't serious or fight back if he is, those are his choices, the same applies for you.

By this he doesn't imply violence Komuro, just in case you were thinking in hitting your friend or something.

And well, yes. Since your friend is pretty much a Gigolo, don'r mind him that much. He just want her for the pleasure of the hunting.

Now, first thing, listen to Fi and hentai. They are right.

Second, FORGET ABOUT TREATING HER LIKE EVERYONE ELSE BECAUSE YOU'R TOO SHY TO SHOW YOUR FEELINGS. Even if you don't land a direct hit, she should know that to you, she's different to everybody else. A woman likes to feel that she's special, so if you show that to her, she will start to notice that you'r serious about her.

The approaching... Uhm... first, DON'T STALK HER! everyone needs his/her space, and we all hate annoying people. Find the right moment to talk to her, have a good and intelligent conversation, and when she show signs of wanting to do something else, don't push her.

Try doing something for others, like who knows, burning music cd's, movies or something, until she gets her turn (and if she doesn't ask for it, you go and make your offer!).

When I was at school, I was always drawing. That by default attracted people and it was easy to establish conversation with however I wanted.

I would go a little more slowly, try by starting some light conversation and kinda "investigate" the whole situation, like interests and such, if she gladly talks to you and you feel that the conversation is going naturally and if she starts to give you more attention than before you can try something more straight forward like if she has a bf or if shes interested in someone, if shes free try grabbing her attention and spending more time with her but not to the level that it becomes a bother, after you got a good look at the situation try asking her out or so, if you realize that she already has an aim you at least wont have to make a move and you save some dignity. The good thing is also if you approach her often other guys will notice how you're getting more intimate with her and give up eventually so that you dont really have to worry about getting her taken away from you, as for your friend since its a race for a girl that is FREE he wont be mad at all if hes a real friend. Try to be as natural as you can and avoid boasting (i really noticed that it annoys girls unless they have no brains) and keep your guard up, if someone approaches her and you feel like he is aiming for her, try getting in between by inviting her for a coffee with some friends, well in the end the thing you have to watch out the most is timing, if you have a good timing sense it will be alright i guess.

Like everyone has said, just try to talk to her first. You shoudn't be intimidated by the fact that your friend likes her too.

It's very important that you build your confidence in yourself. Most girls in high school likes confident guys. Don't be a wimp and just go for it. The best way to live is to live a life with no regrets. Just take a deep breath and go forth with a "Hi!"

Now you don't want to scare her off by announcing right away that you like her. Try to get to know her more and let her know more about you. Talk about the things you like and your hobbies (as well as hers) to fish out what you guys have in common then use that as your converstation starter whenever you need it. Just remember you can't always wait to be sure if she likes you or not before asking her out. Your kind of have a time limit here since you said that your friend likes her too (and i'm certain there might be more guy interested in her). You just have to be brave and quick to get close to her.

Now you said that your "Gigolo" friend like her too. Don't be too threatened about it. The only thing he has that you don't have YET, is confidence. One good way to approach this is to tell him that you like the same girl. You do this only so that you don't get any hard feelings with each other later on (or cock blocks you unintentionally). If he likes this girl as much as you then don't expect him to just let you have her. And even if he does, it doesn't mean you can take your time with her.

So HOW DO YOU BUILD YOUR CONFIDENCE? It's easy.. "Fake it until you make it!". Basically if you have no confidence to start with then just fake it. How? Start by believing in yourself. Go in front of a mirror and tell yourself the things you like bout yourself and what you know your good at (you can say how good looking you are or how amazing you are as a person). Make sure that when your doing this, you look as confident as you can be. Don't look down or shrivel up. Just stand tall and try to feel confident (it's all acting right now anyways so act as confident as you can be). If you do this repeatedly then you'll eventually become more confident about yourself without you noticing it. BTW this works 100%

So just a recap here of the things you hav to keep in mind:

1) Confidence is KEY!
2) Get to know her better but don't take too long
3) Tell your friend you like her too
4) Fake it until you make it!

PS. Don't bother asking when should be the righ time to confess. It's different per situation and person. So the best thing to do here is go with your judgement.