First and foremost to gain respect. I want to be a bad ass mofo because I want to be respected by guys as equals. I don't like to be made fun of for my weight. I also don't get the proper respect from girls either. I also like to stay healthy too.
Next Monday you'll feel more confident. After the gym you'll feel more confident. After one more drink you'll feel more confident. After you get a better haircut, a better jacket, a better job.
You've been "getting ready" for two years.
She's standing ten feet away right now. She'll be gone in four minutes. No amount of preparation will manufacture the courage that only comes from moving your feet.
Walk over. Stumble through the first sentence. Let it be clumsy. Let it be imperfect. You will feel more alive in those ten seconds than you have all month.