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(1) He is in his room with a book.

(2) He is in his room with a table.

Why does (2) sound strange even if it has the same grammatical structure of (1), which works perfectly.

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I think it sounds strange because it's more common to talk about a room having a table. So it's too much like e.g. "he is in the room with a table" (where the "with a table" is telling you which room he's in rather than that he has a table in there) and that makes it take a bit longer to get the correct meaning (it's him that has the table and the room is where he has it). It would help to put a comma after "room" (eg "I'm in the restaurant, with a table. Join me when you can.") – Rupe Jun 11 '14 at 11:29
And of course unlike the meaning of "he's gone to the hospital with his leg" (presumably instead of leaving his leg at home) – AdamV Jun 11 '14 at 16:26

Because when someone is in their room with a book, we can fill in what they are doing that makes the book relevant; viz, they are reading it.

When we are told someone is in their room with a table, there is nothing grammatically incorrect, or even tricky with the preposition (and they can be tricky), it's just a strange thing to say. Why are they with a table? Why would I care? Why bother to tell me?

Now the actual sentence "He is in his room with a book." doesn't explicitly say that "he" is reading that book. Perhaps he is dancing around a copy of Hamlet and invoking the shade of Shakespeare. Perhaps he is using the book for target practice. We're not told that he is not doing these things, but given that there is a particular common activity one might do when alone in a room with a book, we'll fill that in absent any reason not to.

There is not a particular common activity one might do when alone in a room with a table, so we can't fill in the information necessary to understand why we're being told about this table.

This strangeness is different to the strangeness of "He elephant artichoke rubber the minkimoo", which is just nonsense or even "Colourless green ideas sleep furiously" (known words in grammatically correct position conveying no meaning) or "Twas brillig, and the slithy toves. Did gyre and gimble in the wabe" (invented words whose purpose we guess at from their position).

It's the strangeness of a statement that is strange to convey. As such it could be used deliberately:

He is in his room with a table. I don't care who used to own it or how old it is, anyone who spends 2 hours just looking at their furniture should not be allowed to buy antiques.

Here we deliberately baffle a bit, because we go on to express that we think his behaviour is strange, and that moment of bafflement helps convey that opinion. More often, such bafflement will make us think the writer is strange, not their subject.

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Well, there are considerably more hits on google for minkimoo than I expected when I coined that as deliberate gibberish, and of course Urban Dictionary has one related to sex. If a thousand monkeys were given a thousand keyboards, we'd end up with a thousand expressions to which someone had given a sex-related definition on Urban Dictionary. – Jon Hanna Jun 11 '14 at 11:35
"There is not a particular common activity one might do when alone in a room with a table" -- indeed, on reading the sentence I thought, "he must be a carpenter". Although on further reflection maybe I should have thought, "he must be a joiner" ;-) – Steve Jessop Jun 11 '14 at 12:44
@SteveJessop of course, if we already know someone is a carpenter or a japanner or some such, the the sentence "He is in his room with a table" isn't strange in the slightest. – Jon Hanna Jun 11 '14 at 13:05
@JonHanna except that he's in his room with it. That's mildly strange. – JFA Jun 11 '14 at 15:20
@AdamV conversely, in response to "Where's the zoo's new baby elephant?" the book sentence becomes a little bizarre. – Jon Hanna Jun 11 '14 at 18:03

The niceties of prepositional usage are bewildering.

We'd consider it natural to use 'with' to indicate 'alongside [an equal or near-equal]':

He's in his room with his son / the butler / his dog / ??his goldfish.

We'd consider it natural to use 'with' to indicate 'and has the following portable leisure item/s':

He's in his room with a brandy / a book / his collection of foreign coins / his oboe / ??his piano / ??his pressure cooker.

There's an intimacy involved so far.

Obviously, 'He's in the room with the piano' and 'He's doing some daft experiment - he's in his room with the pressure cooker' don't connote intimacy.

So 'He's in his room with a table' would only work when specifying proximity rather than giving an intimacy / cosiness relationship:

He brought five pieces of furniture home from the auctioneers to examine their provenance; he's in his room with a table at this very moment'.

But if he idolises the table:

He's in his room with that precious table.

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I don't think the matter of either proximity or intimacy are the cause of the strangeness. I can imagine someone being proximate to a table, and I can even imagine someone being intimate with one, though I'd much prefer not to. What I can't do is jump to a particular reason for being "with" a table in any sense, though I can with a book (to read it) or a companion (to spend time with them). – Jon Hanna Jun 11 '14 at 11:32
This doesn't explain the fact that you'd say 'with his violin' but not 'with his piano', when one assumes that 'he' can do comparable things on both. – Edwin Ashworth Jun 11 '14 at 17:00
@EdwinAshworth This appears to depend on the mobility of the object. When a piano is in a room, it generally doesn't move too often. The violin can be anywhere. – Cruncher Jun 11 '14 at 20:24
Hence 'portable' in the answer above. – Edwin Ashworth Jun 11 '14 at 20:55
I personally feel that the sentence "He's in his room with his piano" is perfectly normal. It's like "He's spending a good time in his room expressing himself with his piano" – justhalf Jun 12 '14 at 3:11

Where is Joey?
He is in his room with a book.

I don't think I would say this, unless I was pretty sure Joey was actively reading the book. If the book was simply neglected on the floor, or collecting dust on a shelf, it wouldn't be pertinent to the conversation. I would simply say, "He is in his room."

Where is Joey?
He is in his room with a table.

I'm having trouble envisioning when I would say this. If there is a table in Joey's room, and he's working on a project there, I might say, "He is in his room, at the table."

There is more than one way we could interpret with. Prepositions are tricky that way. (By the way, did I ever tell you that I once shot an elephant in my pajamas?) If we are trying to emphasize that Joey happens to be in a room that contains a book, there's no need to make such a clarification, because it's his room – although we might say something like:

He is in a room with a book.

In other words, the inclusion of a possessive pronoun also contributes to the strangeness of your second sentence. After all,

He is in a room with a table.

doesn't sound nearly as awkward as the sentence you inquire about.

Bottom line: it's not merely syntax, it's also context.

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If I am not mistaken, this could be a misplaced/ambiguous modifier. "He is in the room with a book" implies that he as a book and is in the room. It could mean he is in a room that contains a book, but that doesn't seem to be common useage. "He has a book in the room" may be clearer, but not by much.

"He is in the room with a table" is where it gets tricky. A table, being less moble, does not seem to be something you are 'with'. You can stand by it, sit at it, lay on it, etc. The sentence implies possesion, which is not common usage for a generally stationary object.

By separating the last portion, as Rupe stated in the comment, can be used to clarify whether he carried the table in there, or whether he entered a room containing a table rather than one containing desk, bed, etc.

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Hello, JSM. OP takes the precaution of using 'He's in his room with an X' to try to forestall the identifier ('He's in the room which has an X') usage. – Edwin Ashworth Jun 11 '14 at 19:49
Aha, missed that. I think it still holds true; "He is in his car with a dog" vs "He is in his car with a seatbelt". Same principle. Does he have two cars, one with a dog and one with a seatbelt? Even changing it to 'a', as in "He is in a room with a book/table" is somewhat vague. At this point, I have to say it depends on the context. – JSM Jun 12 '14 at 16:23
The classic ambiguous case for 'what is the prepositional phrase modifying' is He was watching the man with a telescope. – Edwin Ashworth Jun 12 '14 at 16:28
Or the classic, "She was walking the dog in a bikini." This one lends itself well to visual aids :) – JSM Jun 13 '14 at 17:05

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