I'm always somewhat wary of posting fairly personal stuff on a forum that I'm not massively active on, but this thread is pretty interesting and is about stuff that's been on my mind lately.
Growing up I was always pretty uncomfortable with the way I looked/was - I was shy, retreating, a bit odd looking, significantly taller than most of my class mates (something that wasn't really an asset until later) and generally pretty geeky. I considered myself a pretty nice guy and generally worthwhile in a personality sense, but I had no self-confidence and spent a lot of time at home playing computer games and reading. However, over the last few years I have 'blossomed', as it were. I was never fat, but I was certainly carrying more weight than was flattering on me until I left school, at which point I lost a lot of it. I still put weight on in odd places, and struggle to stave off a beer belly, but generally I'm okay. I should eat better and do more exercise, and I am improving in this regard. I think the first year of university, with the heavy drinking, occasional drug use, lack of sleep and general antics have actually had a physical effect on me, as I look significantly older/a lot less baby-faced these days, which is an improvement - perhaps a little haggard, in comparison, but it all adds character. I have also learnt what to do with my hair and how to dress more flatteringly, and developed an ability to grow a pretty great beard, although I tend not to these days, and have a generally dark complexion that often leads people to think I am of Mediterranean descent (often these people are themselves Mediterranean, which is incredibly flattering). Coming back from travelling this year, my self-esteem pretty much sky-rocketed as various friends commented on how good I was looking and, for once, I could see it. I also received flattering comments from random internet people, which was lovely, too. Overall these days, I am incredibly happy with the way I look - I have my off days, like everyone, but they're much rarer now.
Oddly, though, my improved self-image has not led to much of an increase in confidence with the ladies. These days when girls are looking at me, I tend to assume that they may well find me attractive (in fact, sometimes my ego is ridiculous in this regard). However, I'm not all that confident with approaching girls - I know I can be interesting and fun, but I'm also crap at idle chit-chat and am uncomfortable approaching girls I don't know because I feel pretty creepy doing so. On top of this, I have a horrible habit of falling for close friends, which I rarely actually act upon as I know how horribly awkward it can be when a good friend suddenly tells you they're into you and you don't feel the same. I also tend to go for quieter, more retreating girls as I struggle with spending long amounts of time with louder, more intense people. The Catch-22, though, is that as a guy who does not approach girls very often, I only really get to know ones who approach me, and these tend to be, by their very nature, the louder, more intense type.
So, yeah, I'm my self-image is great. My ability with girls, however, still needs some work.
Also, I started going grey at 17 and I think it's fucking awesome. In my family it's either premature greying or premature balding, and I know which I prefer!