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I remember receiving emails titled "Gentle Reminder" from University administrative staff. But I am not sure if this is a friendly phrase. You may be wondering what I mean by friendly. Let me give you an example of what I have in mind:

  • Please take off your shoes before entering the house. - friendly

  • Kindly take off your shoes before entering the house. - not friendly

[Well, at least that's what I have been told.]

The reason I am asking about the phrase "Gentle Reminder" is that I want to write a short note reminding my referee (person who writes reference letters for me) that the letter is due in a few days. Would "Gentle Reminder" be a friendly phrase to use in this context?:

Hi, XXX,

Just a gentle reminder that the reference letter for the position of [name of position] is due on XXX. Thanks very much.

Thanks!

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    I don't understand why one of those would be "friendly" and one "not friendly" - the only differences is please vs. kindly. "Kindly" is slightly more formal, if that's what you mean, but it's not unfriendly. Less friendly might be simply "Take off your shoes before entering the house" or "You must take off your shoes before entering the house."
    – stangdon
    Commented Jul 13, 2016 at 12:12
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    I understand why you might have been told "Kindly do this" is not friendly even though the words look OK. "Kindly do this" is often used (in AmE anyway) when people are irritated or frustrated and trying to demand you do something but remain polite. For example, Olympics Fans Asked to Kindly Stop Tweeting So Damn Much or Dear Warner Bros: Kindly stop producing giant, bloated messes.
    – ColleenV
    Commented Jul 13, 2016 at 13:16
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    Personally, I don't really think that this overly-kind phrasing is necessary. It looks like you're walking on eggshells around whomever you're sending this message to.
    – Catija
    Commented Jul 13, 2016 at 13:26

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Interesting. This might be a matter of opinion, since neither

  1. Please take off your shoes before entering the house.
  2. Kindly take off your shoes before entering the house.

seem friendly to me. I think most people would agree that they are polite, but not necessarily friendly. It would also depend on the speaker's tone, if it was spoken. If it is said in a friendly tone, then you could take it to be friendly. If it is said sternly, then it might not be as friendly.

Regarding "gentle reminder", yes this seems friendly. I don't think I have ever heard or read it before. But what I have seen and heard is

friendly reminder
Just a friendly reminder that the reference letter for the position...

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    To me, both options sound kind. But I'm not sure what the OP was trying to say with being friendly. In an email like that, the example above would be enough. (IMO)
    – burcu
    Commented Jul 13, 2016 at 4:22

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