Does anybody know at what point in the history of English (in England) it became possible to say, e.g:-
"Who are you going out with tonight?"
i.e. not only reversing the two words "with" and "whom" but actually separating them.
A linked question is when did "whom" first become optional in everyday speech? I imagine that it was once obligatory, as "him", "her", "them", etc., still are, after prepositions and as the objects of verbs.

Regards,
Adetola Obembe.
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A linked question is when did "whom" first become optional in everyday speech? I imagine that it was once obligatory, as "him", "her", "them", etc., still are, after prepositions and as the objects of verbs.

Instead of "obligatory", did you perhaps mean to
say "natural"?
\\P. Schultz
Adetola Obembe:
A linked question is when did "whom" first become optional in everyday speech? ...

The OED1 lists the objective use of "who" as a separate sense, or rather two separate senses (pronoun and conjunction). The two earliest cites have only approximate dates, 1300 and 1400 respectively. The first cite with an exact date is from 1450. (Only one of these three actually uses the spelling "who", but it's the same word.)

Mark Brader Safire's Rule on Who-Whom:
Toronto "Whenever 'whom' sounds correct, recast the sentence." (Email Removed) William Safire, NY Times Magazine

My text in this article is in the public domain.
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Instead of "obligatory", did you perhaps mean to say "natural"?

I've just looked up various definitions of "obligatory" on the web. The following best describes what I meant to say:-
Imposed on one by authority, command, or convention

- in this case, convention. What I really meant was, was there a time when there was no known grammatical alternative to "whom" to any native English speaker? For example, by convention, no one speaking even informal or colloquial standard English today would say: "I'm speaking to he" - though I understand that in parts of Gloucestershire, the locals use "he", "we", and "they" when standard English speakers would use "him", "them", or "us", e.g. "Them doesn't like we!" Similarly, I imagined there was a time when it would never have occurred to any native English speaker to use "who" instead of "whom" after a preposition or as the object of a verb.

I wouldn't use the word "natural" in this respect though, as grammatical usage is not something we're born with - it's a matter of consensus and convention within any linguistic community at any particular time.

You're obviously interested in semantics, as I am, so why did you think my use of "obligatory" was perhaps incorrect?
Regards,
Adetola.
The two earliest cites have only approximate dates, 1300 and 1400 respectively. The first cite with an exact date is from 1450.

Thanks, Mark. I'm astonished. I imagined it would have been an early 20th century phenomenon, 19th century at most - probably because I've never seen it used in any 19th century novels, even when characters from the "lower" classes are speaking.
Regards,
Adetola.
The two earliest cites have only approximate dates, 1300 and 1400 respectively. The first cite with an exact date is from 1450.

Thanks, Mark. I'm astonished. I imagined it would have been an early 20th century phenomenon, 19th century at most - probably because I've never seen it used in any 19th century novels, even when characters from the "lower" classes are speaking.

I tested Literaturepost.com's collection to see. I use Google for that because they don't have a good search tool of their own, or they didn't use to. Try this: go to Google.com and paste in:
site:www.literaturepost.com "whom are you going"
and also run a search on
site:www.literaturepost.com "who are you going"
I think you'll be interested. It doesn't answer your question of how far this goes back, though.

Best Donna Richoux
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Thanks, Donna. The "who are you going" search was the more interesting of the two. Obviously my observations on 19th century literature were completely wrong. Apparently the Victorians etc. weren't quite as "correct" as I'd imagined. And the site too is an excellent resource.

Regards,
Adetola.
What I really meant was, was there a time when there was no known grammatical alternative to "whom" to any native English speaker? For example, by convention, no one speaking even informal or colloquial standard English today would say: "I'm speaking to he"

But they DO say "It's difficult for my wife and I
to plan a vacation." It is a general and pervasive usage, employed by millions of educated people.
It is easy to be misled by the fact that the
choice of pronoun form often lines up with what
would have been the appropriate grammatical case
if grammatical case still existed. That feature
constitutes a mere bathtub ring, left over from a
former system. The roles of the "I/me, he/him",
etc, forms of the pronouns have been floating and
morphing ever since English lost its inflexional
system beginning in the 11th century. There are
parallels in other languages (e.g., French: "C'est moi qui l'ai fait").
\\P. Schultz
But they DO say "It's difficult for my wife and I to plan a vacation." It is a general and pervasive usage, employed by millions of educated people.

Though perversely it's because such people know "my wife and I are planning a vacation" and not "my wife and me are planning one". As for "for my wife and I", they use it because they self-consciously believe it to be correct. The same people often revert to "for my wife and me" in their less self-conscious moments. However, any youngster hearing this may un-self-consciously adopt it, unaware it's someone else's mistaken and self-conscious idea of speaking "correctly", and so it perpetuates itself.
The roles of the "I/me, he/him", etc, forms of the pronouns have been floating and morphing ever since English lost its inflexional system beginning in the 11th century. There are parallels in other languages (e.g., French: "C'est moi qui l'ai fait").

I still do believe in case for pronouns, morphing as it does. For instance, most people would answer: "Me" or "I did" or "It was me", and rarely "I" or "It was I", to "Who did that?" (assuming they'd done it and were honest). So "me" in that sense is obviously cognate with the French "moi" (can you remember the term for this French usage?) and could be regarded as a special case.
Regards,
Adetola.
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