How do I stop being shy and cowardly

This question confuses me.

"First off the friend group I have doesn’t fit me, I’ve had girlfriends and they never have for example."

Just made my fucking head explode, what does that mean exactly? What friend group would you prefer? Are you saying your friends aren't as cowardly as you? Are you a.. guy?

If you hear a girl is into you a fun thing to do is make her pee her pants by approaching her in a very friendly way. I mean come on, the moment you hear someone digs you, you should automatically understand the prospect that is... "YOU'VE ALREADY IMPRESSED HER", now go make her fuckin' day grand by saying hello. What would you possibly have to lose at that point?

Ok so let me try to make this simple. How to stop being shy cowardly... well it's bullshit when people say "oh you just have to be confident in yourself". It's like, no shit that's what you're trying to do right?

What works for me is to constantly ask yourself "why" and "why not"

You see a girl who you know likes you that you want to approach. Your head says,
"I'm scared...", ask yourself why, more than likely its for an idiotic reason
"what if I say something stupid",...
- "why not say something casual instead like 'what's up?'" "what if she laughs at me?"
- " why the fuck would she laugh at you, you're just saying hi, she already likes you so it's not like you have to impress her"
"I'm not great at talking, how can i talk to her without talking" - "just show eye contact and smile at her, are you seriously THAT insecure to fear rejection of a smile?"

The mind conversations can go on and on, but instead of giving yourself a reason NOT to do something, try playing devils advocate in reverse and see how far that gets you.

I guess I don't really understand what you are trying to say. So what if your friends haven't dated, if you enjoy being around them then be around them. Unless you want to be friends with some players or something. But anyway, just because a person hasn't dated anyone doesn't mean they are shy, I'm assuming you're young, like high school so I mean not everyone dates, in my whole group of friends no one has dated besides me and it's no big deal. School and whatnot is more important to us. If you want more friends then make them, talk to people in your classes or something, hang out with them through that and whatnot. Or join a club, a sport, something like that to bond with people of similar interest. And if you hear a girl is into you, just talk to her it's as simple as that, it's even more simpler for you because she won't say no if you ask her on a date or something. Anyway have a good one.

Have you ever thought about being someone you're not for a bit until you find the true, unshy you?(:

You shouldn't refer to yourself as "cowardly". It is difficult for anyone to step out of his or her comfort zone, especially to make a move your current crowd probably won't understand. Clearly you're craving something different from life than what you have now. Sounds clique, but don't let life pass you by. I feel it's important to put yourself out there, take a risk and possibly (probably) end up happier later on. Think ahead of how badly you could feel if you remain idle only to look back later and feel regretful. Finding friends that "get you" can be difficult, but won't it be worth it when you find a few people that are going through the same kinds of things you are, that understand you, that you could be totally comfortable around? How much do the opinions of people that don't get you really matter? Don't miss out on happiness because you're concerned about what people might think. I realize that making a move toward change sounds much easier than it actually is, but you can do it. I truly wish you the best :)