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When is it possible to say for instance:

Perhaps you could help me with that.
I would really appreciate it if you could compare this one with:
  • Would you please help me with that?
  • Can you please help me with that?
  • I wonder if you could help me with that.
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Being tentative by using words like these can be polite.

All of your examples are similarly polite.

At some point tentativeness starts seeming a parody of politeness, or even "passive aggressive".

If you are being politely tentative, you should be happy for the person to say "no". If you are using tentative language to try to manipulate someone then you are being passive aggressive. But only you know if you are really asking if something is possible, or if you would be upset if the person says its not possible.

Among polite people, the default assumption is usually that the other person is being polite, especially in the case of a non-native speaker, so that a request not phrased as an order will usually be received without offence.

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  • Do you mean that in the English language or custom, it is not the word choice but rather whether you could say no feeling no pressure that defines the politeness?
    – Taro
    Commented Dec 20, 2021 at 10:14
  • It can be hard to tell if a particular set of words are meant to be polite. There isn't a simple formula "this sentence scores 7/10 on the politeness scale". It helps if you can hear the intonation, and if you know the person. But don't worry too much about it. There's no need to be that tentative, but also there is nothing rude about it either.
    – James K
    Commented Dec 20, 2021 at 10:38
  • Yes. Among polite people, the default assumption is usually that the other person is being polite, especially in the case of a non-native speaker, so that a request not phrased as an order will usually be received without offence.
    – Michael Harvey
    Commented Dec 20, 2021 at 12:58
  • Intonation makes a great deal of difference. A native speaker might say sarcastically 'Perhaps you could help me with that?' when they mean 'Shut up, I know what I am doing', but a non-native speaker would be unlikely to make that error.
    – Michael Harvey
    Commented Dec 20, 2021 at 13:01
  • +1 and to add that while I think "Perhaps you could..." is usually passive aggressive, if it's coming from a superior, like your boss, then it could be a nice way to ask you to do something while trying to avoid sounding too demanding or authoritative.
    – gotube ♦
    Commented Dec 20, 2021 at 23:26

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