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Any tips on doing this? I'm #15 out of 40 on the waitlist (this is for next semester, obviously), so I doubt I'll get in. Should I wait until after add/drop anyway? Or is it the sooner the better?

I have good, articulable reasons for wanting to take the class btw. And he advised me on a short written project, so he knows who I am but we're not super-tight.

If the class is elective, explain how the class is relevant to your future career. If you're a 3L and the class is only offered sporadically, explain that you will miss out.

If you're just a 2l and your reasons are just scheduling, suck it up and wake up earlier on registration day next year.