Fighting for out of your league

I've had a lot of time to think recently, and to be a bit more alone than I normally am. Being on planes flying around the world, screwing with your sleeping patterns, and having a couple more days from work will do that a guy I guess.  Plus drinking by yourself might have its usefulness. All joking aside and with the above being said, I think I've had an epiphany, or maybe I'm finally able to put into words, something that I've been thinking about for a long time now.

I always seem to be interested in girls that are far out of my league. 

Whether I try to talk myself into the fact that she isn't, to try to calm myself down, the fact of the matter though, is that she always is. Every girl that I've ever been fully interested in has been so amazingly far out of my league. The question that keeps popping up in my head though (and I don't have a solid answer for) ... Do I continue doing that to myself (I'm not getting any younger you know)? Do I continue to be interested in girls that are so far out of my league? And if the answer continues to be yes, then I need to learn, at some point in the very near future, to stop getting discouraged if it doesn't work out or I don't really get a chance.  Because it's really not meant to work out in the first place. The hardest part of continuing down this destructive path I have myself on, will be to stop getting discouraged time after time. To realize that I would need it to really work but one time, just one time, it will work out and then I'll have found that absolutely amazing girl that I've been chasing for my lifetime. I guess the real epiphany comes in realizing that the reason I always chase after girls out of my league, is because of an incessant need to find someone that is better than me. Someone to learn from, someone to grow with, and someone to be a better person because of. I've always liked the quote "If you're the smartest person in the room, then you're in the wrong room", but I seem to be only just realizing that I'm actually trying to live that way.

At the end of the day, I'll have to keep trying. So maybe I have my answer after all.  I don't know any other way, and it really only takes one chance after all, right? Like Blake Shelton says, in his song "Over" ... "I don't wanna fall asleep alone, and wake up knowing that I died without the one."

Honesty

Do people really want honesty?  This is something that I struggle with often.

When someone asks me a question ... 1) If I know you well enough, should I tell you exactly what I think?  2)  If I know you well enough, should I tell you what you ultimately want to hear?  3)  If I don't know you that well, should I just lie to you because you won't know the difference anyway?

I feel like there are actually some people in this world that want to know the truth, for better or for worse, because they are actually trying to become better people or learn more about themselves.  The problem, I find, is the tweeners ... the people that tell others they want to hear the truth, but then use that truth to prove that you were wrong, don't know what you're talking about, or just don't believe that's what you just said.

By trait I am pretty shy, actually I'd say reserved.  I'm probably the most perfect combination of my mother and father that you could possibly get.  A chameleon, if you must ... someone that's quite shy, however can hold a conversation with just about anyone, and in the right situation can feel quite comfortable holding that conversation.  I'd like to change.  I'd like to become more out going, as I've gotten older.  I'd like to be able to tell everyone the truth, but that's the problem.  That's where the "more out going" turns into "going back to what I've always known".  Avoiding confrontation is something that I do really well ... I've taken tests to prove that.

It seems to me that people don't want others to be more out going by becoming more truthful ... they want others to become more out going by just doing whatever the group is doing.  Hopefully my observations are skewed or even flat out wrong.  I'm not sure I'd be happy living in a place where I'm trying to always be a chameleon, in the sense that I need to change in order for people to accept me.