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There is a sentence like below.

He looked at her with a hurt expression.

I don't know whether he has a hurt expression or she (her) has a hurt expression.

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He looked at her with a hurt expression

with a hurt expression is a prepositional phrase: it can modify a verb or a noun.

If it modifies the verb, it describes the way in which he is looking (the expression on his face). It wouldn't really work with talk, because with at hurt expression can't really describe the way you talk... but it does work with look.

If it modifies a noun, it functions like an adjective- it can either be descriptive (she is tall) or determining (the tall woman). Neither of these works with her: for descriptive usage, the noun must be a subject form she, and it is not necessary to use a determining form with her because, in order to use the pronoun, we must already know who it refers to.

In this case, therefore, it can only modify the verb, describing the way that he is looking at her.

The following sentence could be interpreted both ways, because the man can be followed by a determining with-clause- one that defines which particular man we are talking about:

He looked at [the man with a hurt expression] - with-phrase applies to the man
He looked at [the man] with a hurt expression - with-phrase applies to looked

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    I noticed that all the examples I used in my answer had nouns/noun phrases and not pronouns (this is that holy **** moment for me). I wasn't aware that the presence of "her" in OP's example is a key element that makes the sentence unambiguous. Great answer!
    – AIQ
    Nov 4, 2019 at 7:37
  • It could be ambiguous with an indefinite pronoun, eg He wanted someone with a zest for life (though it's hard to come up with an example of a modifier that makes sense both ways).
    – Colin Fine
    Nov 4, 2019 at 10:27
  • @ColinFine Yes, the reason that 'her' doesn't work is that it's already definite, so you can't use it with a determining with-clause. When you use an indefinite pronoun, you can definitely use it with a determining with-clause. ... though you can say "she who must be obeyed"...
    – JavaLatte
    Nov 4, 2019 at 11:20
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    @JavaLatte: You can really only say she who must be obeyed because it is a set phrase. The original was not only 19th century and literary, but a special use anyway: the novel is called She.
    – Colin Fine
    Nov 4, 2019 at 12:12
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He looked at her with a hurt expression

I believe that the sentence is not ambiguous since the verb look at looked holds good for her ( object) and with a hurt expression(prepositional phrase)

He looked at her with a hurt expression.

This can be analyzed this way:

Who did he look at ?- her

How did he look at her?- with a hurt expression.

In any way we analyse this sentence, the prepositional phrase which is an adjunct refers back to He but not her.

So there is no ambiguity of who has a hurt expression.It is undoubtedly he who has a hurt expression.

The sentence is not ambiguous because of the pronoun her. If it is an indefinite pronoun or a noun , it becomes ambiguous.

He looked at somebody with a hurt expression

It may mean that either he has a hurt expression or somebody has a hurt expression.

He looked at the stranger with a hurt expression

This sentence means that either he has a hurt expression or the stranger has a hurt expression.

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  • The word "because" is generally used to introduce an argument for a proposition, not simply restate the proposition.
    – Acccumulation
    Nov 4, 2019 at 6:06

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