Well anyway, there is this girl, who is hot, cool, funny, and ect. And I think she likes me and I like her but she's a grade higher than me, would it be a little weird for us two go out with that grade difference?
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.