New to the pill, at least in this context.

First, some background:

I am hoping to be transfering to a 4 year state school in the fall of 2019, and want to be able to make the most of my time in college. I'll be 24, so I would think that would already put me at a social disadvantage being older than almost everyone else. I'd like to hone my social skills before then so when I get there I can feel confident in my social abilities and not have to worry whether college will live up to my expectations or not. I plan on probably pledging a fraternity (mostly for business connections and brotherhood, but the parties and shit are obvy a plus too) as I've been told by a current student at the school ill be attending that there is one on campus that has a lot of ROTC kids, is full of cool dudes, and probably wouldn't mind having an older veteran around. The whole year and a half I've been at this post I've had fuck all for a social life and contact with women. All male unit, and the surrounding town is shitty as fuck with nothing to do but a couple shitty bars full of drunk soldiers and STD ridden women. We're not allowed to go out of town without approval from our command. My buddy and I said fuck it and went to the beach this past weekend, and decided we're gonna make it a regular thing this summer. I want to use this to my advantage and start brushing back up on and improving my social skills greatly.

Now about my buddy:

Reasonably naturally good looking (7ish?) IF he takes care of himself which he doesn't. He doesn't care about his appearance or the impression he makes on others. He dresses lousily (pretty much only wears jeans that are too big, band t shirts that are too small). He was in a bar at the beach in basketball shorts that didn't fit and nike slides (yeah it's the beach, nobody expects you to wear a three piece suit but that doesn't mean look like you're homeless). He's had girls negatively comment on how he was dressed before (not a shit test). On top of that he regularly holds a frame of being "out-chadded" by others. Dude is one of my bestfriends and I love him to death, but I'm sorry, I just don't want to approach girls with him. I try to take care of myself and I take pride in my appearance, I don't want his lack of doing so to drive my SMV down. I'm also reasonably good looking (girls have told me I'm anywhere from a 7 to a 9, I've had decent looking girls approach me before, grab me as I'm walking through the bar, come up behind me and smack my ass (aka assault me)) and am working on getting back in the gym and getting swole again. There's not really anybody else I have to go to the beach with that won't end up getting on my nerves within 2 hours.

So, am I fucked up here or am I justified in my concerns? If I am justified, how do I get through to him to start taking better care of himself so we can have a good summer together and start spinning some plates?