When to use ‘who’ and when to use ‘whom’ seems to be one of the most common areas of confusion for English learners, and even possibly for native speakers. Personally, I don't find it confusing at all and (although I am no grammarian, as reflected in my answer) I even tried to reply to one of those questions in April 2017, my first month at ELU:
Conflicting who/whom usage rules in a sentence
I later found that members regularly and repeatedly ask about ‘who’ and ‘whom’ here:
https://english.stackexchange.com/search?q=Who+whom
‘Who and whom’ questions also get asked at other grammar websites with great regularity.
So linguistically speaking, what is it about ‘who’ and ‘whom’ that is so difficult for so many new learners?
Non-native speakers trying to improve their English often tend to go by rules rather than usage. Could it be that the 'rule' covering the use of who and whom is itself complex, ambiguous or contradictory?
Note: I am not asking what is the difference between who and whom, so somebody please don't close this question as a duplicate unless someone has previously asked specifically why who & whom create such difficulty for so many learners.
Nor is it primarily opinion-based if you can quote standard references or expert commentators to support your answer.
Answer
I think there are a few reasons:
Most people are not great at taking an explicit grammar rule and just adopting it; rather, we're much better at internalizing rules when we also have exposure to language that conforms to those rules. Since whom is rarely and inconsistently used, most people don't have enough exposure to it to get a good sense of when it's used.
Most people (including most English teachers, most popular grammar and style writers, etc.) are not great at formulating explicit grammar rules, partly because they don't give a coherent overarching grammatical framework that those rules can fit into. Normally that doesn't make much difference because the explicit grammar rules aren't really how you learn grammar, but with something like whom where explicit grammar rules are almost all you've got, this is a problem.
- In the specific case of whom, a large part of the problem is that it often sits at the intersection of two clauses, yet explanations of it never seem to worry about that.
There's a close relationship between who/whom and certain other areas where traditional grammar differs from everyday English:
When to use subject vs. object pronouns. Do we say "It is me", or "It is I"? "Me and Jamie", or "Jamie and me", or "Jamie and I"? "She is taller than him", or "She is taller than I"?
Preposition stranding vs. pied piping. Do we say "that we spoke of", or "of which we spoke"?
So when trying to understand the grammar of whom, we also have to balance all the other pieces of formal grammar that we don't usually worry about.The grammar of whom is often somewhat "long-range", in that the pronoun can be separated from the verb or preposition that it's the subject or object of. Consider this bit from Daniel Defoe's 1719 novel Robinson Crusoe:
This ſeaſon I found my family to encreaſe; for one of my cats that ran away from me, and whom I thought had been dead, returned about Auguſt, with three kittens at her heels, like herſelf, which I thought ſtrange, because […] [link]
where whom is erroneously being used as the subject of had, apparently because the writer (or narrator) felt it to be the object of I thought. You'll see this sort of mistake even with points of grammar that are not common sources of confusion; you'll encounter things like "Talking to people you don't know, about things you don't understand, sometimes make you look foolish" [made-up example], where make should be makes, but where the singular-ness of talking has become less salient by the time the speaker got to the verb.
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