I need relationship advice. (Long)

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First off, let me say that typing this out to a group of people on a forum is very nerve wracking. The people I am talking about could very easily see this. It would be obvious to them who I was talking about. Which would just suck complete balls.

Okay, so first let me introduce the two girls:

Basically. 2004 (Junior year in highschool) I started dating a girl. We have been dating off and on until very recently. More often than not, it was on. With a month or two separation here and there. We lived together, she knows me more than anybody else. We argue A LOT. She would do just about anything for me. When I'm with her, it seems boring, or stale. I can't help but resent her a lot of the time, or be annoyed by some of the things that she does. Also, (this sounds bad) over the years she has become less physically attractive to me. I can't tell her this, as that would just be rude. I am not in love with her, but I am very close to her. We've been hooking up recently out of what feels like loneliness and desperation.

Two years ago. During the biggest separation between the first girl and I, I met another girl, and befriended her alarmingly fast. She, and her sister (as well as their parents) have become like my second family. I spend probably 3 nights a week at her house. I don't ever have anything bad to say about her, and I don't think I have ever gotten sick of her. She has a lot of the same issues I have, except she pulls it off remarkably well. I've found that lately I am wondering if I am in love with this girl. Or if we are just really good friends. I don't think about her physically that much, but I'd be lying if I said I didn't want to date her. We are incredibly close, and to be honest, I probably think about her way more than I should.

The issue I am having, is that this girl is liked by EVERYBODY. I'm not exaggerating. Every single guy I know (and some women actually) want her. She refuses just about everybody. Getting no further than a kiss with select people. She breaks up normally after a few days, after finding some flaw. She claims to be incredibly shallow. Also, whenever she does break it off with somebody, or realize that somebody likes her when she doesn't like them back she becomes incredibly awkward around them. Won't talk to them, and has a hard time just being near them. She consistently puts me down in a joking manner. Having AS I have an incredibly hard time reading her, I can't tell if she is flirting, being a b***h, or neither. She has said before that she would NEVER date me. However, I've also said the same thing about her in the past. I also have such incredible feelings of self loathing that to me, she seems so far out of my league it's not even funny.

I feel like if I asked her out, and she said no, it would make our friendship nearly impossible to keep on such a high level. Also, same outcome if we broke up after a short period of time (as is normal with her). So, I often find myself defaulting to my ex which truth be told, isn't fair to my ex, or me. We also have such a tight group of friends, that it would not only ruin my relationship with her, but many of my very close friends as well. I can't ask her out unless I KNOW she would say yes. However, trying to figure that out is driving me crazy. There don't seem to be any real ways to go about finding out what she would say, without implying that I want to ask. Well... not ones that hadn't become transparent as of 5th grade anyway. I just want to find a way to either be with her, and in love, or to get over her, and find somebody else. But right now, in my head, she is SO perfect, that I end up comparing any dates I get to her and... they never match up.

Holy crap that was long, I guess I just kind of ended up venting, my bad. ;\

The first girl is a crutch. Crutches aren't bad, and in fact are a necessity during certain times of life (e.g. when you get into an accident and wreck a leg/hip). Nothing wrong with going back to her with you (and preferably both of you) knowing it's a temporary relationship.

For the second, I recognize your risks and concerns. She's a crutch of a different type. Not only is she a friend, but she seems to have the qualities which you find worthwhile

So how do you broach the subject w/o risking the friendship?

"Hey, you ever thought about us dating?" "What would you say if I asked you out on a date, a serious date?" "I wonder, we've been friends for a while, do you ever think of this turning into something more serious?"

Basically you are looking at finding out her feelings without comitting your own. Do not say "I love you" and then stare blankly. This will cause most people to stutter, stammer and then try to get away unless those feelings are present AND ready to come out also (only in movies).

If, and ONLY if, you are absolutely certain that the girl you actually like does not want to date you ever, then you need to get over her and try to see her less. Trust me, I was in a similar situation in the past to yourself and, yes, it is tough, but you have to persevere for the sake of your own sanity. If you carry on seeing her as regularly as you are without accepting that you will only ever be friends, then you will hurt yourself greatly, that's if you are not doing this already. However, if the opposite is true, get in there and good luck . And as for this on/off thing you seem to have with this other girl who seems to annoy you, if it isn't really doing you any good, stop seeing her. There is no point in seeing someone who you would rather not bother with when you could be engaging in a hobby instead or, perhaps, looking for a different girl who you may come to prefer over your actual current choice...