I have always hated getting haircuts. In fact, I've always kinda hated my hair... I didn't think it looked good "just short", or spiked with gel as was the fad in my day, or buzzed off, or - when I got older - long. It just never quite looked cool in my opinion.
Maybe that's why I've always dreaded getting haircuts so much. I was a pretty mild kid, so the sitting still part didn't really bother me, so I don't really know why I hated it so when I was little but I did - so I always asked to just keep getting a "chili bowl". I rocked that look for years. And years.
Then I started doing the whole gel thing, mostly spiking some short hair, but never really felt like that fit me either - I have a big forehead, and I was too critical on myself because of it. This was probably junior high through high school, then when I got a little older, out of high school, I just kinda stopped getting it cut for awhile, and let it grow out. I kinda liked that except it felt kinda weird having to own a brush suddenly, and I still didn't really think the look fit me... but I did get some backlash when I decided to go ahead and cut it back off, so I thought "meh, maybe this is my best option" and grew it back out a second time. And then it started to happen...
I first noticed it in the shower. I would have a few long strands of hair on my hands. I ignored it for awhile, knowing that "Hey, hair falls out, then it regrows. That's just how it works." Deep down though I thought it looked like too much, and I got kinda nervous about it. I was in my very early twenties, probably right at 21 or maybe 22. Sure enough, my hairline had already begun receding... as if I didn't already lack enough confidence in talking to girls.
I'm in my upper twenties now, and I look very similar to my blood uncle, who has had the same thing going on for as long as I can remember. My family has always commented on how much I look like him, but now it's really uncanny. I've gone with short hair since then, and even started doing buzz cuts just to be done with it because if you have any amount of hair that you can control how it looks due to its length, you will likely care too much to just leave it alone. So my solution: buzz it all off, it is what it is!
I think that's the proper approach when dealing with this sort of thing. Ultimately, I realize how fortunate I am not to have any serious diseases or chronic pain of any sort or anything like that... it is simply cosmetic, which, doesn't matter. I do believe that, but it doesn't mean it's not hard to have confidence with the ladies.
Be that as it may, I would also like to point out that I know of at least three - count 'em, 3 - other guys roughly my age that have a similar situation going on, so I know I'm not alone at least... and hopefully if any other guys with this dilemma happen to cross this writing, they'll know they aren't either. It is what it is, buzz it!