I was born into a family of good looking people. Its just in our genetics. They are very vain, and I mean VERY!! When you bring a girlfriend home (me or any of my cousins, my brother etc), our girlfriends always get analysed, talked about how pretty (or not) they are. My grandad even tells every girlfriend to come in the family, we dont want any ugly girls in this family!! (All my cousins are guys except for one who is only 3).
As a young kid I was always one of the most popular (if not the most popular kid in my school), invited to all the parties, everyone picked me for their sporting teams etc etc. Every adult who knew me said I was made in life because people are just draw to my personality and energy. However I still was not that confident. As I got older (like 12-16), I simply started to practically do no sports and eat a lot of junk food. I got acne (not a real bad case but reasonably bad), enough to crush my confidence. I put on weight, and became quiet chubby. I lost my confidence even in sports (which is basically my life), I was teased by some people and my confidence was simply crushed. Some days I would even cry before going to school. All my family was like, ohh poor CLOONEY, all his cousins and brothers are popular, good looking, have beautiful girlfriends and he has nothing. lol, only further crushing me. Then at like 16 I thought, fukc this, I took up boxing religously (this boosted my confidence temendously), I got in great shape, I went to a skin specialist and got my skin cleared up (I have naturally very smooth skin, like a pretty boy, lol, but with all the zits you couldnt see it properly, now I am asked by people what I use to make my skin look like "peeches and cream"), haha.
So, by the time I was 19, I had perfect skin, was in awesome shape, started buying HEAPS of new clothes, and generally working on my confidence. I started getting a hell of a lot of puzzy and my familiy started to say, WTF, CLOONEY is now the best looking in the entire family, lol. Even my mum would yell out to people, this is my son!! hahahaha, omg! I was even told I was too beautiful for the family (although not really, a couple of my cousins are models paid very handsomly)! We just look very different to eachother! Nyways, then I noticed I was like Dirtheart mentioned, obsessed with my looks, I wanted to be better looking than EVERYONE, thinking this would give me confidence. So I started to change my outlook, realising I could not get every girl, and those I couldnt, who cares. I built an inner confidence more, and realised that you have to dig deep when times get tough, your exterior wont help you push on and through the challenges life throws at you, it will simply let you enjoy your time out in the public arena more and perhaps add to your charisma etc, as looks are definately interpreted as confidence and a trait others aspire too. However like I said, it dose not help with the hard times in life and it does not get you any girl you want.
Nyways, that is my story......not sure if it will help anyone, but its the story of my "ugly duckling phase".