Well, good news: I've lost 14 lbs in this past month! Bad news: I still have a ways to go to get to a weight I think I'll be happy with.
Well, I'm at a point where I at least feel confident enough to start putting some effort into my appearance again. It's been about 8 months since I've had a haircut, so it's long enough that I have plenty of options. As well, I'm a firm believer that you have to think about your hair-cut when deciding what to do about facial-hair (ie. you don't want a super-sculpted beard with messy hair).
Right now, these are kind of the three choices I'm thinking about:
1. The "Surfer guy" look. Just leave my hair kind of long and let it hang in my face. I know a lot of girls seem to dig that look on guys, but I question whether that would work with a heavier guy. Not the way I'm leaning, but just keeping an open mind. I'm thinking with a really light beard. I have red-hair, and as much as people joke on it, I would argue that the actual hair-color looks pretty good when it's longer (it's just the pale skin and freckles that come with it that suck :P).
2. The "clean-cut" look. Basically, just basic short hair, cropped on the sides, a tad messier on top. Probably keep it clean-shaven, or maybe a chin-only goatee and maybe slightly longer sideburns. It's nothing super interesting or anything, but it's obviously a Classic look, and might look more natural.
3. The "Bald guy" look. I'm hesitant to go with this, because honestly, I'm a "ginger", so I'm pale as shit, lol. On the other hand, it seems like it would be really comfortable, and worse case scenario, I'm overweight anyways, so I'll just grow it back out as I continue to lose weight. Plus, it seems like when a guy *is* able to pull off the bald look, it seems like girls *REALLY* like it. Not saying I could pull it off, but... who knows?