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The problem with me is that I applied to 4 programs and I didn't get in in any of them. The last program which was almost guaranteed admission (because I already found a researcher willing to accept me); I emailed my undergrad thesis supervisor for, what I called at the time of the email "my last reference letter request ever to make". Unfortunately, I wasn't accepted to the program and now I'm applying again to a different school.
The problem is I feel so weird about emailing him again for another reference letter. Other than the generic email, how can I go about emailing him? I am sure he remembers me , but I don't know how to justify the amount of requests that I've sent him so far !

Any idea on how I should approach the issue?

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    I'd say that 4 is not that many. I am currently, probably, upwards of 20ish. Honestly, I lost count. I have very patient advisors/supervisors... – Fábio Dias Jul 16 '17 at 21:42
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    I'd agree, four is not that many. All the supervisor has to do is to keep a word document and then change possibly one or two details on it. As well, many places accept electronic replies. – jim Jul 16 '17 at 21:51
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    When I was about to apply for grad school, I was advised to apply to a dozen or so places (maybe more). For various reasons I ended up not following that advice, but "feeling weird emailing my advisor" was not one of them (the advice came from one of the prospective letter-writers). – darij grinberg Jul 16 '17 at 21:53
  • /@darijgrinberg how did you go about emailing your supervisor? I feel that I am emailing him literally the same email everytime :/ – Emma Jul 16 '17 at 22:26
  • Why don't you keep the Original and send copies? If I were your supervisior I would be slightly annoyed, but if you are polite, he won't ruin your career. Don't make promises you can't keep ;) The same Email every time is not nice, even you have the same request. Use other words for same request (so one can see your effort). – BitAccesser Jul 17 '17 at 7:03
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You haven't asked for too many. Write to your supervisor, tell him what happened, and ask whether he will write "a few" more reference letters. People will generally be willing to help you if they understand the reasons for your requests. (Do not ask for "one more" or you could find yourself in the same situation again.)

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    It's also important to note that the first letter takes longer to write than any subsequent letters. I am usually happy to provide additional letters because I only need to tweak my original letter. – Ben Norris Jul 17 '17 at 0:13
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    Supervisors know what they're getting themselves into when they have students, and that includes N reference letters where N can be arbitrarily large. They all had their own supervisors write them N' such letters, and they understand that this is how they can pay it forward. Good luck with your applications! – Greg Martin Jul 17 '17 at 4:44
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When my students ask me to write letters of reference to graduate programs, I ask them to provide me with a list of all the programs they intend to apply to, with deadlines. I do tell them "it's OK if one or two gets added or dropped off as time goes on; I just need to know when these letters will need to be submitted." It helps that in my field, most of the application deadlines are spread out over a relatively narrow time frame (about 2 months, from December–February) and so my students are unlikely to add extra programs later in the "application season." I definitely don't want an individual e-mail from a student for each program they apply to, if they can avoid it.

As to "how many is too many": In my field, this list is typically in the range of 8–12 programs. I once had a student who sent me a list of 20 programs spread across three or four different fields. I will confess that I got a little annoyed by the number of letters I had to write in that case (especially because I had to change my letter around for each of the different field that the student was interested in.) But I understood that it was part of my job, and I didn't let this annoyance affect the letter I wrote.

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