Jason,There is always something that a person would like to change about himself/herself, but I think you're being too hard on yourself. From my picture, my head shape looks pretty good, but from the side, it's oblong, and I don't like it. I always tend to check out other shaved heads, and I get jealous when I see a perfectly round head. So it's normal to be apprehensive, but once you shave your head, you will probably just obsess about getting it perfectly smooth (nothing wrong with that). I know it might seem harder for you since you're younger, but hey, I didn't have my first relationship with someone until I was 25 (married her by the way), and I was already losing my hair. If you already have your hair extremely short, there is not going to be much of a change when you shave it as far as what others will see. Most guys here seem to have found the reaction to be a non-event. Don't mess with surgery though, or you could end up looking like this: http://www.snopes.com/photos/people/jackson.asp We're here for you future sly bro.
Jason, I would say shave it just like most have said before me. I don't know of one of my bald headed brothers out there who are totally happy with their dome but they wear the look and feel great about it. A friend of mine has a great shaped dome (I think) and I see my imperfections. I always say that I would like his shape and he says he has issues too and likes the look of my dome. I say go for it, it is not as bad as you think it is.