I thought about it and it seems they can often be substituted for one another? Is this the case? When would you use each of them?

  1. He glared back at his brother, to which his brother told him to go out of the house with him.
  2. He glared back at his brother, after which his brother told him to go out of the house with him.
  3. He glared back at his brother, at which his brother told him to go out of the house with him.

Are these sentences interchangeable?

  • I mean, how come you concluded if these are synonyms?
    – user17814
    Dec 29, 2018 at 19:36
  • It changes the meaning, but not by much.
    – JJJJ
    Dec 29, 2018 at 19:56
  • Your second sentence is interchangeable with "He glared back at his brother. His brother ( redundant ) told him to go out of the house with him ( redundant ) after ( what ). Does it make sense?
    – user17814
    Dec 29, 2018 at 20:10

2 Answers 2


I had answered the question about this on the ELU site. I am taking the liberty of reposting my answer here:

The trick to knowing how to use; of which, at which, in which, to which, from which (etc.) is to analyse the prepositional phrases, phrasal verbs, verbs and prepositions in a sentence and then see how it can be transformed:

He /spoke of/ war and peace and many other topics that day. The topic /of which he spoke/ was complex. The verb here that means to speak about a topic is /to speak/ of a topic/: to mention

The party /at which/ he spoke/ was noisy. Phrase: A party is held /at a place/. It is implied.

The situation /in which/ we found ourselves was dire. Phrase: /to find oneself /in a situation.

The bonds /from which/ we broke free were tight. phrase: to /break free/ from bonds.

The town /to which/we were driving was 50 ks away. phrase: to /drive/ to a place.

Summary (and not a complete answer but a general one): The preposition depends on the verb that takes a preposition, a phrasal verb that includes a preposition, or it depends on the prepositional phrase used. Also, there are many other prepositions that can be paired with which: under, during, about, over, etc.


I would regard all of these sentences as being ones that were not written in English by a native English speaker. The phrase "glared back to his brother" is awkward and unnatural, as is "told him to go out of the house with him."

That said, the highlighted prepositions are not interchangeable. The first one implies that the brother responded to being glared at; the second merely that the brother "told him" after the glaring had occurred (the brother may not have even seen the glare). The third is another awkward preposition here; it sounds like the brother is responding to the glare, but it is not the way a native English speaker would put it. I suppose there is an implication that the brother is not only responding to it, but that his response is somehow directed at the person's glaring.

  • I don't think not the way a native English speaker would put it is the right way to describe at in this context. It's a well-established (if somewhat "literary") usage. For example, Stretching out her hand, she very gently laid it on his chest, at which he stirred and sighed. In that exact context, neither to nor after would be acceptable to a native speaker. Dec 29, 2018 at 18:11
  • Why not? Could you explain?
    – JJJJ
    Dec 29, 2018 at 19:26
  • Agree with rcook 100%. Plus, repeating "his brother" is redundant. +1
    – user17814
    Dec 29, 2018 at 19:39
  • @FumbleFingers, let's explore that a little. Your example sounds like one could replace "at" with "in response to" -- "...she laid her hand on his chest, in response to which he stirred and sighed." So we could try: "He glared at his brother, at which his brother told him to leave.", and then: "He glared at his brother, in response to which he told him to leave." I suppose that can work. It took several readings to realize that the brother must have been staring at him already, so "back" had a context I hadn't realized before. The double use of "at" is a bit jarring, but not incorrect.
    – rcook
    Dec 29, 2018 at 19:43
  • Well, "at" obviously does work in my cited example. Also in I raised my hands in a gesture of conciliation, at which they stepped back and the spears the men carried were lifted. But in neither of those does it seem natural to replace "at" with "to", even though "in response to" seems like reasonable paraphrasing for both. I think maybe "at" implies "impromptu, reflexive" response, but I don't really know. I just know that in some contexts it's the only preposition that really works well. Dec 30, 2018 at 13:25

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