Search Results: i need to relax around her

Ok so im 14 and on a scale of 1/10 im a 5 or a 6 at max (appearance wise). So yea im not the most handsome guy you'll ever see but Im not disturbingly ugly by any means. I have a lot of friends and I would say 80% of the people who know me, like me as a person. Im quite confident and relaxed around girls and something I pride myself about is my sense of humor. I can make basically everyone laugh (girls included) without like humiliating myself or something. Just plain old humor. However, I'm not that "successful" with girls my age. I have had 2 girlfriends before with who out relationships were like 1-2 months long. I'll stop bubbling now. For the past year or so I have been talking to a really hot girl my age but almost only through texts. She has been throwing hints here and there but nothing major that I could REALLY say "oh she likes me". The problem is that she's really stupid and doesn't have an exciting character so during this time that we were talking I wasn't so into her. However, for a while now (1 month or so) I'm thinking of her very often and I really like her (yes suddenly). We will both be at the same Island for holidays in a few days and we have told each other to meet up there if possible. The problem is that even though I believe I have a good chance with her I can't get off my mind that "dude. She's out of your league" thing. Is it really true? Or do I have a chance? Should I go for it? And if yes, how should I approach her?
If you have read this whole thing thank you so much! Sorry if I have some mistakes here and there I'm from Greece... Anyway I would be SO happy if someone can answer me this question :) thank you again for reading all this thing and I hope you answer me!

My ex girlfriend of 2 years broke up with me just over 3 months ago because she felt I wasn't as in to her as she was to me, at the time this was partially true although I did love her and treat her well. She was VERY into me for 2 years. We were initially on a break period for a few weeks and met up on dates a few times so I as 'fairly' relaxed about it as I felt we would sort it out. During this time I came to realise what I wanted and on the third occasion I told her I wanted her, I was very much in love and wanted to get back together. Ironically she said she didn't know what she wanted anymore. I later found out she had dated a guy twice shortly after we broke up. I was crushed.

After a few more weeks I persuaded her to meet up for a date to see how things would go. It was amazing. She invited herself back to my house, although nothing happened. I did try to kiss her but she turned away, saying she hadn't kissed anyone in a while and wasn't sure she remembered how (cop out!). Ok so nothing happened with the other guy I thought which was good. She told me the next day it was wonderful, and that she was very sure everything would be fine with us and she felt very positive she just needed some space and wanted to see her friends more after being in a long relationship. We would go out again.

So I asked her out again a couple of weeks later after she had finished some studies she had going on. She took two days to reply and said she was sick and could we reschedule. Bearing in mind my emotions were running high I got a bit pissed off and thought she was messing me around. I decided to also wait a few days to say ok and eventually called her and it was a nice conversation and we would go out again.

A couple of days later I spotted on Facebook she had booked a holiday with a friend to go away. After we had spoken on our date about going away together.

To be continued...