Cool is short lived, cool is shallow, cool is what people clump around thinking they are supposed to.
What attracts guys to girls isn't that different from what attracts girls to guys - niceness.
You will SEE mean girls and mean guys with friends hanging on their every word, but it's fake, and it doesn't last any longer than a song stays # 1.
So say little compliments and friendly interested things as you pass by, and keep walking.
Don't get too personal and don't plant yourself in front of him.
You might go 2 weeks just saying Hi or Wasn't that exam awful, and if he totally ignores you, that's your clue to not go the next step.
If he responds, then you say Hey I like that shirt or Do you think you'd ever join the orchestra.
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