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Suppose I want to use the phrase "many, many" to compound the "maniness" of the thing I'm describing.

There are many, many people.

The people (of which there are many, many)

The first one is standard, but the second one is contended. Can it be used in that way?

An example of one that wouldn't be so awkward is:

There are lots and lots of people.

The people (of which there are lots and lots)

Each one can be properly used in its singular form, but once repeated, one of them falls apart. Why?

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This is strictly spoken or informal written English. Unless you're writing some kind of serious formal report, business letter, or academic paper that's going to be published in a reputable journal, it shouldn't matter. Who's gonna contend that "many, many" is unreasonable colloquial English? I'd still say "very many people", "myriad people", or "scads of people" instead of "many, many", & certainly anything, even "hordes of people" is better than "lots & lots", which, IMHO, is a sign of limited imagination & perhaps VGS (Valley Girlitosis Syndrome): We are talking usage & style here. –  user21497 Jan 17 '13 at 14:14
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But @BillFranke the OP is asking whether the second line can be used at all ("The people (of which there are many, many)"). My answer is no, it can't, but I couldn't tell you why. Good question. –  JAM Jan 17 '13 at 14:51
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@JAM: Sure the second line can be used in colloquial English. Why not? You say "no" probably for the same reason I'd say "Change it" if I were asked to edit it: I don't like the style. But there's nothing ungrammatical or unnatural about it in spoken or informal written English. Maybe it's awkward because it crosses registers: "which there were many, many of" is consistent, but "of which there were many, many" is inconsistent. ..."of which there were many" seems consistent to me. One of my American friends says "tiny small towns" and "little small towns" all the time! :-( –  user21497 Jan 17 '13 at 14:59
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2 Answers

This is best reserved for the spoken word I think. Use one "many" to convey the meaning, or revise the sentence using a different word, like "multitude," for example.

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One issue is that you are using many, many to compound the number. It doesn't do that: it simply emphasises many. Where an adjective is simply repeated for emphasis, you can't repeat it in the style of your second sentence.

My love is like a red, red rose
*My love is like a rose which is red, red.

However, it can work if you need it for emphasis in the second form:

My love is like a rose which is red, red!

...but that is quite a particular use.

The phrase lots and lots doesn't work in the same way: it's effectively a single unit, just as red or many is. Because it's a single adjectival phrase and not repeated, you can place it at the end of the sentence.

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Perhaps lots and lots works better as a stand alone phrase because lots is a noun. –  bib Jan 17 '13 at 18:48
    
Those familiar with the vintage BBC radio programmes 'Round the Horne' and 'Beyond our Ken' will perhaps remember Betty Marsden's oft repeated line 'Many times. Many, many times.' –  Barrie England Jan 17 '13 at 21:34
    
Perhaps I misused "compound" in the OP; I certainly meant something that meant the same as "emphasize". –  Joe Z. Jan 17 '13 at 23:18
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@JoeZeng Whatever; the point is that "lots and lots" is a single "unit" just as "many" is, and you can only have one such "unit" at the end of the sentence. Unless you want to shout "red!" contradicting a statement "Ha! Your love is a blue rose." –  Andrew Leach Jan 18 '13 at 7:11
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