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For easier handling of the examples, let's define two persons - Mike and Janet.

Compare the following statements:

Janet says: "Mike, don't bet on my thinking everything will be OK. You'll have to reassure others too."

Would this mean it's Janet who is doing the thinking?

versus

Janet says: "Mike, don't bet on me thinking everything will be OK. You'll have to hire other people too."

Would this mean it's Mike who is doing the thinking?

Is this difference strictly grammatically correct or is there a better way to distinguish between those two situations?

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RiMMER Ψ, then should not "my thinking" be "me thinking" in your first example? –  Nikita Dec 30 '11 at 20:55
    
@Mahnax I was very confused :) –  Nikita Dec 30 '11 at 22:35
    
If this question is intended to explore the subtleties of various contrived interpretations, I think it's a very bad idea to muddy the waters with me/my. If not, why don't we just have Janet say to Mike "Don't bet on me/my leaving". Which is all I can see in play here. –  FumbleFingers Dec 31 '11 at 1:18
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I think it would be meaningless to put a comma after "thinking". You could put a semi-colon: "Don't bet on me thinking; everything will be okay." That means Mike can safely bet that Janet will not think, and therefore everything will be okay. This might make sense if whenever Janet starts thinking she does something crazy. :-) –  Jay Dec 31 '11 at 5:16
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CRAZY JANET! –  Pureferret Dec 31 '11 at 14:32
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6 Answers

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In the first sentence, my is part of the subordinate clause, not an argument of the main clause. Here my functions as the subject of thinking, and my thinking everything will be OK is the complement of on.

The second sentence is ambiguous. It could be exactly like the first sentence in structure, simply with me alternating for my. Today genitives like my as the subject of a subordinate clause are characteristics of a formal style.

Alternatively, me could be the object of on, which would make it an argument of the main clause. In this case, thinking... is an adjunct to the main clause with the implied subject of thinking being Mike. A comma before thinking (or a pause in speech) would clearly lead to the second interpretation.

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This is my most favorite answer so far. Let's see how the bounty changes things! –  RiMMER Aug 15 '12 at 8:04
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No, both of them mean that Janet is doing the thinking. Only in directly quoted speech do personal pronouns retain their original referent in English: in reported speech, they are substituted by pronouns relative to current speaker.

John said "They were looking at me."

means that they were looking at John, but

John said (that) they were looking at me.

means that they were looking at whoever said this, not at John.

To get the second meaning, you cannot have "me"/"my" - but "don't bet on you(r) thinking" would be odd: I would say something like "don't rely on thinking", though probably I would avoid the gerund entirely "Don't bet that you can" or something like that.

The difference between your two examples is stylistic. Old fashioned prescriptive grammar taught a bizarre rule that "don't bet on me thinking" was ungrammatical and you were supposed to say "don't bet on my thinking", but the former has been in common use since before this rule was invented. See Gerund with genitive.

Edit: with the comma after "me", the "thinking" becomes a participle, and could indeed refer either to the subject (Mike) or the object ("me", i.e. Janet). I missed that reading.

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Colin, do you agree that the following is correct? "Don't kill my reputation saying I slept with Janet." If so, why according to the same rule wouldn't the following work too? "Don't bet on me thinking everything will be OK." –  RiMMER Dec 30 '11 at 21:51
    
@RiMMERΨ: OK, I understand what you're saying now. With a comma after "me", the second sentence is ambiguous - the object is then "me", and "thinking" is a participle introducing a parenthetic phrase, which might modify either the subject or the object. I took it as a gerund functioning as (part of) the object. I didn't notice the other interpretation at all. –  Colin Fine Dec 30 '11 at 22:13
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@RiMMERΨ: I think if you want that second (IMHO contrived) meaning, you probably shouldn't use the word "bet" at all. A more logical choice in that context would be "Don't rely on me, thinking it'll all be okay", but really it need complete rephrasing. For the most obvious interpretation, me/my thinking are equivalent, so you can't involve them in subtle semantic twists. –  FumbleFingers Dec 31 '11 at 1:27
    
@FumbleFingers and ColineFine: I still don't think the comma is supposed to be there at all. –  RiMMER Dec 31 '11 at 1:44
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@RiMMERΨ: If you want the thinking to be Mike's, you're stretching things with this general form of words. The comma would help that interpretation, but if you really don't want it, how about changing "don't bet on me thinking..." to "don't bet on me and think everything will be OK." But I still think the question is flawed, because you're jumbling up an irrelevant me/my issue with a contrived scenario/interpretation. –  FumbleFingers Dec 31 '11 at 4:02
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The two sentences have exactly the same meaning. Janet is doing the thinking both times. The question is whether you believe, like Fowler, that a noun or pronoun followed by a gerund should be in the possessive form, or agree with his protagonist Jespersen that using the objective pronoun has a perfectly respectable history.

According to Burchfield in the New Fowler's, with personal pronouns, usage is equally divided. I think in informal use, at least, most of us use the objective form when the gerund is the object, as in your examples, but are more likely to use the possessive when it is the subject:

My smoking at table annoys her.

There is a very good article on the question at Merriam-Webster Dictionary of English Usage:

http://books.google.com/books?id=2yJusP0vrdgC&pg=PA753

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Expanding on this, we have When is a gerund supposed to be preceded by a possessive pronoun? with an excellent accepted answer. –  RegDwigнt Aug 15 '12 at 18:46
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Technically, neither sentence means anyone is doing any thinking (beyond the minimum required for verbalization, of course). In both cases, Janet is dissuading Mike from making any expectations about an event of thinking that everything will be OK, where that event either belongs to or is associated with Janet (version 1) or is explicitly done by Janet (version 2). Even in version 1, Janet can be expected to be the one hypothetically doing the thinking, barring any intensely philosophical notions of "thought."

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This is a spurious distinction. As @Colin says, me/my thinking are simply stylistic variations - unless you accept the baseless grammarian's prescription that the former is ungrammatical, which I think puts you in the minority among native English speakers. –  FumbleFingers Dec 31 '11 at 1:08
    
@FumbleFingers, perhaps you misread jwodder's answer? –  jwpat7 Aug 17 '12 at 15:23
    
@jwpat7: He seems to be making a semantic distinction, and I don't think there is one. –  FumbleFingers Aug 17 '12 at 16:39
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The lonely comma after the first word of the quote causes the confusion and lack of flow. Try instead…

Janet says to Mike: “Don't bet on my thinking everything will be OK. You'll have to reassure others too.”

Janet says to Mike: “Don't bet on me thinking everything will be OK. You'll have to hire other people too.”

It would be even better to rephrase altogether, removing unnecessary negatives (don't) combined with passive voice (-ing ending words.) In fact the “don't bet” construct is flimsy and vague in the sentences.

Without OP specifying exactly what the meaning was meant to be, I'm still perplexed with what was the true intent of the sentences.

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Chris, I think your remarks about FS's post are valid, pertinent, and should be acted upon (by FS in editing the post into answerable form). But you don't address any of the three question-punctuated items in FS's post; you could have written your remarks in a comment to FS's post. –  jwpat7 Aug 17 '12 at 15:20
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The point you don't bring out is that the second sentence isn't a gerund at all. Because you use hire later, a careful reader can deduce that thinking is the start of a second clause; strictly speaking this could be indicated by a comma after me, but it would be far better to replace thinking with in the belief that. If you did that, it would be clear that Mike was doing the thinking (or believing).

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