Dear Garrett,
First of all, don't care too much about what other people think of you. They have their own shit to deal with, and you are at best an after-thought.
Fuck playing sports for anything but fun with your friends. All that's going to do is give you bad knees and back when you get older. Join the drama club and maybe even the choir even though you think the guys that do that are fags and your friends will laugh at you. You will get laid by accident in the environment, and it will hone some of your true talent early on.
Talk to every girl you want to hook up with, but don't appear to be over-eager. Make a play for every girl you want, but take rejection gracefully when it comes because that can pay off later. Don't assume any girl is out of your league. It's hard enough to get laid already---you don't need to provide them with another reason to not fuck you. They're going to fuck someone, it might as well be you as much as the next douchebag. No one girl is that important, and they are like a bus: there will always be another one along.
Take your grades seriously, go straight to Ohio State for a communications degree, and pledge Sigma Chi, as it's a great frat and you are a legacy. Hit up the gramps for the cash. He will be cool with it and he knows your Dad is a cheapskate that will never understand the benefit of a frat. I know frats may seem silly and conformist, but you will get top-shelf pussy all the way through college without even trying and you'll make valuable business contacts that pay off for the rest of your life. And don't whine because you're dying to escape Ohio winters---it's only four years, and that's no time at all in the grand scheme of things. And trust me, you don't want to live with your Dad anyway---he's a shitty influence.
Move to LA right after college and focus on making contacts in comedy/writing, because that's where your talent truly lies. Work hard at it, and ignore distractions the best you can. Focus, focus, focus! No one is going to give you a free pass because you think you're brilliant----there's no substitute for paying your dues and making connections. Along those lines, come up with a trick that allows you to remember people's names and stick with it.
If you decide to stay on the east cost, make sure you move to NYC as soon as possible and follow the above paragraph. Be sure to start seeing a band called Phish, out of Vermont, in 1989. They will blow your mind and you will have the time of your life seeing them for years to come. Also, don't choose the music you listen to based on what your friends like, or what seems cool. Just because it's not heavy metal does NOT mean it sucks! Make sure you get into The Smiths, The Clash, and The Replacements as soon as possible and see them live when you get the chance.
Experiment with drugs, as they can be among life's finest rewards, but try to lay off smoking pot every day. While it may make life more fun in the short term, it comes at the cost of killing motivation to better yourself. On the other hand, be sure to keep some xanax around for when you really, really could use a good ten hours of sleep.
Don't go over five or ten miles over the speed limit. You're only going to get there a few minutes later anyway, and the cumulative costs of fines, insurance, etc. of being cited will waste thousands of dollars. And speaking of that, don't buy that ring for Julianna, either. That's not going to end well.
And lastly, spend a lot more time on your chipping and your putting.
Best of luck,
Old Garrett
