re: Letter of recs from professors.

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I'm assuming I should ask professors who I've already taken as opposed to ones I'm currently taking. Does it really matter?

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Yes, ask for letters from profs who you've taken multiple courses with; the ones who actually know who you are and are familiar with your work. That will allow them to personalize the letter. If you ask for letters from profs who don't know you very well, you can expect a generic, unremarkable letter - IF the prof remembers to write it and submit it by the due date.

There is also a culture of hyperbole when it comes to these things, and a prof who doesn't know you isn't going to put his/her name on the line for somebody they don't know. And even if you aren't applying to Harvard, these letters are still read carefully, esp. if you're applying for funding like an assistantship or fellowship.