1. If you have difficulty articulating your feelings, don't worry first about not sounding right. As you learn to open up and be honest (no matter how you sound, using whatever vocabulary makes you comfortable) about how you feel, with practice you will be able to express your emotions better.
2. Why imagine? Why not just feel?
When you are out with your friends, think whatever you want to think. As cliche as it sounds, be yourself. Of course respect others and display some common courtesy when you're out with them, but being genuine is the best way to go. If you relax a little bit and not worry so much about how you should do things or how you should feel, things will run much smoother for you.
When you are in situations you do not feel secure in, trying to limit yourself with "how-to's" and instructions will limit your progress. When you first began to play football, you made mistakes. By recognizing the boundaries through free play of the field in regards to these unknown-situations, you will be able to better handle yourself the next time such an event arises.
What do you believe your purpose should be when being with others? You said it yourself - you want to be the cool guy everyone wants to talk to. But why? Does being around others who admire you and are pleased by your presence make you feel better? By reading through your explanation of football and school, it seems that you place a lot of importance on how others think of you. Knowing how they think of you allows you to adjust to these circumstances accordingly. What would you do in the case if a group of people did not like your company? Would you try to adjust your behavior to fit them?
Your goal is clear, it's just that you have so many thoughts and emotions regarding the process of how to achieve this goal that it makes you second-guess what it is. I think you are worrying too much about what is right and what is wrong. Do what you feel is best.
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