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I'm a non-native English speaker and I have a troubling question. What is the difference in terms of usage of "when" and "where"?

"The fact that my action was so embarrassing singled me out to the point [when/where] my friends asked me if I did so on purpose."

"She was angry to the point [where/when] she punched him and broke his pair of glasses."

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The word POINT can refer to a place or a time, therefore a relative adverb WHERE or WHEN can be used respectively leading a relative clause as a modifier. However, in Longman, it says WHERE is used whether the word refers to a place or a time, whereas in Oxford, an example clearly shows: We had reached the point when there was no money left. Please help specify. Thanks.

So does this mean we can use the two interchangably?

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    Even more idiomatically in your examples: just use that. “To the point that…” sounds more natural than either here, at least to me.
    – Janus Bahs Jacquet
    Commented Jun 21, 2015 at 7:05
  • To me, "to the point that" sounds familiar, but grammatically poor. Heh heh.
    – Misha R
    Commented Jun 21, 2015 at 14:20
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    Depends on the metaphor. Is it a real, physical Point, that you can point at with your finger? If so, where. If, on the other hand, it's merely one metaphoric point on the trail of a movement or a process or a story or something that changes in time, then you can use when (though where is also OK).
    – John Lawler
    Commented Jun 21, 2015 at 15:42

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The Oxford example is not the same as your example. Their usage of "point" is directly linked to the situation, marking a point in time. Therefore, "when" is appropriate.

In your example, my assumption is that you don't mean "until." Rather, you are talking about the extent of being singled out. When talking about extent, use "where."

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