Ok.
STOP.
I don't want to regurgitate the same **** that I'm sure you've heard time and time again back at you but I want you to READ very carefully. I want you to take this to heart, because it's the truth. Because if you really accept this, I firmly believe that it will be one of the most productive steps you can take towards being a better you. Ready?
If you want to be succesful, not just with women, but with life in general (and they dont come in that order) you need to eliminate negativity from your life.
Let that sink in. It means so much more than what it appears at face value. Of course, you can't expect bad things never to happen. The driving point here is that you learn how to turn the negative things that happen to you in to a positive experience. The key to this is perspective. Accept things that don't go how you had hoped as lessons learned. Analyze where you went wrong, and correct it. Each time, you will come closer and closer to getting to where you want to be.
The other absolute truth is that it's not the hand that your dealt, but how you play your cards. Everybody has strengths and weaknesses. Make note of each. Magnify your strengths, and do all that you can to improve in areas where you aren't so strong. To me, it sounds like you are a bit self conscious, its ok. Everybody is. Thats a weakness. But you cant let that stand in your way or it will shake your ability to think positive, and in turn your confidence. By allowing your confidence to be shaken, you are stopping yourself from being the best man that you can be. Just by posting here, you've demonstrated a willingness to change, which is a fine line from motivation, and not much further off from ambition, a definite strength.
You were probably hoping for a more immediate solution to what appears to be your biggest roadblock - body image.
Just as with any other weakness, you need to look at it as the enemy. And crush it. How do you do that? Set goals.
Ex.
Issue 1: "I'm uncomfortable about my receding hairline"
Solution: Either pick a new hairstyle, or go with a close buzz - not bald. You have a head shape that would be complimented well with a buzz. If you dont like it, grow it back. Its a very masculine hair cut - Think Jason Statham, Bruce Willis. It works well for them. Each have receding hairlines, and similar shaped heads to yours. It may work for you too.
Issue 2: "I'd like to be more physically fit. I understand it's importance, but dont have the money for a gym membership"
Solution: Three parts go in to fitness, each bears great importance. The first is nutrition (not diet), second is exercise, third is rest.
Nutrition - Your body needs fuel to perform exercise, and to recover from that exercise during rest. You wouldn't fuel your car with ****ty, watered down fuel. Why then would you fuel the only body you get with ****. Eat healthy, its not as hard as it sounds and if you do it right, you dont have to count calories - focus on feeding yourself as many natural foods as you can. If you cant immediately identify what plant or animal it came from, dont eat it. Have as many complex carbs and natural sources or protein as you like. You'll feel better and have more energy. Drink lots of water. Avoid simple carbohydrates and excessive amounts of sugars and fats. It may involve a lifestyle change, but the end result is more than worth it. Google clean eating.
Exercise - Once you have the right fuel, your ability to perform improves. Make the most of it. It doesn't have to be expensive, it just involves going out and getting physical activity on a consistent basis. Both aerobic and anerobic. Try to run or jog 3 days a week. MAKE time for it, and commit to it. Your body will reward you in time. 2 days a week, do resistance training. Save up for dumb bells or a weight bench. They aren't terribly expensive. In the mean time, perform body weight exercises. Pushups, dips, squats. If they get easy, there are hundreds of variations on each to make them harder. Run monday, lift tuesday, jog wednessday, run thursday, lift friday. Rest saturday and sunday. Be honest about your fitness. There is a wealth of information online about how to pick a training program that works for you. This too, involves a lifestyle change, but is well worth the effort.
Rest - Your body needs time to recover, just like your cellphone or laptop needs time to plug in and recharge, so do you. Best to sleep at night, wake in the morning and do your physical activity before school/daily tasks. Establish rhythem and regularity. Find your balance. Its worth it.
If you do these things, you will see a rapid change in your fitness, confidence, and well being.
Issue 3: "I want to improve my appearence. I want to like what I see in the mirror"
Solution: Get a job. Learn to budget. Get a checking, and savings account - preferrably at different banks. The money in your checking account is for immediate spending - the money in your savings account is to stack up for large purchases like a car, school, hair transplant, whatever is important to you.
The checking money is whats important now. Use the money to buy things to improve your appearence. Invest in clothes that look good, and fit you. Its better to have a smaller wardrobe of nice clothes that you are comfortable in then a larger wardrobe of generic clothes that lack style. You dont need to be rich - check ebay, and take time building your wardrobe. Integrate them into a staggered rotation so you never wear the same thing twice in a week.
Build your wardrobe to include:
7 pairs of nice jeans.
7 pairs of sweat pants/basketball shorts/casual house wear/workout pants
7 plain t-shirts/undershirts
7 nice t-shirts that fit well and define you
3 button downs
2 pairs khakis
2 pairs tennis shoes/sneakers. One for daily wear, the other to go out with.
1 pair of boots
1 pair dress shoes
1 pair workout shoes
1 nice jacket
3 generic, and two nice hoodies
1 nice coat
And atleast 7 pairs of socks and boxer briefs.
Pick styles that work for you, and when in doubt, take female friends shopping with you. Take care of your clothes. Do laundry weekly. Iron and hang jeans, button downs, and nice t's. Fold everything else. Buy shoe polish and clean your kicks weekly, preferrably on laundry day so they become complimenting habits. A well dressed man projects confidence and commands attention. See if your body image doesnt improve with a good hair cut, chisled physique, and nice crisp clothes.
It's nearly 2010 for christ sake. Manscape. Invest in face wash, exfoliators, moisturizers. Establish a skin care routine and follow it religiously. Women love a man who cares about his appearence, this builds and projects confidence. Get a straight razor and electric trimmer. Once youve picked your hairstyles, facial and otherwise find a barber you like and have him maintain it weekly. In between your weekly appointments at the barbershop, do your best to maintain them yourself. Tip your barber. Its classy, and motivates him to do the best work he can for you. Buy several different colognes - two for casual use, and two high end scents for dates or nights out. Experiment and find what scents work for you, again, female friends are helpful.
Get these things down. Thats one weakness out of the way. Identify your other weaknesses, set goals and achieve them. Set and achieve goals to improve on your strengths as well. Keep busy, focus on your own happiness. Do this for you, and nobody else. Soon, you may not even need to worry about chasing girls - you will become a prize and they will come to you. This is called your inner game. After you have that, you can work at improving your outer game, and learn to enjoy rather than fear the -- ahem. "Finer things in life"
I hope you read this, and put as much effort into implementing it as I did writing it for you. If you take this to heart, I guarentee your life will improve. Read it. Live it. Get off your ass and do it! Take control of your life now, and be the man your destined to be.