I have two sentences here whose meanings are confusing to me as they are interpreted by native speakers.
1) "When Jack did all the shopping, he went to the cafe."
Means: On the days that Jack did all of the shopping, he (also) went to the cafe. (a regular (repeated) action in the past)
2) When I paid her one dollar, she answered my question.
Means: I paid her a dollar, and (in exchange) she answered my question. (A one-off action)
Do you agree with this interpretation of the meanings? If yes, what is the factor which determines when it should be understood as a one-off action in the past (2) or a regular action in the past (1)?
On the top of that.
Some natives say that:
1) "When Jack did all the shopping, he went to the cafe." – can be changed to (3) "When Jack had finished all the shopping, he went to the café." and it will mean a one-off action in the past.
Why is it not necessary to change (2) “When I paid her one dollar, she answered my question.” to (4) “When I HAD paid her one dollar, she answered my question.” in order to get a meaning of a one-off action?
Best Answer
In everyday constructions such as those that the OP presents, when may be used in either of two senses:
or
The sense of when that the speaker intends is necessarily contextual, and the meaning that a hearer attributes to the speaker's words in everyday situations may at times involve some rather subtle distinctions. Our default handling of a single past event is to use when plus a simple past tense, as in the OP's second example:
If we want to describe a recurring situation in the past, our usual tactic is to change when to whenever:
However, the OP's first example
doesn't follow this normal pattern. Here our tendency (as hearers or readers) is to understand when to mean "on every occasion that" (that is, "whenever") rather than "on a particular occasion that." I suspect that the reason we shift to the "whenever" understanding of when in this case is, in large part, that the cause-and-effect relationship between "Jack did all the shopping" and "he went to the café" is far more tenuous than the one between "when I paid her one dollar" and "she answered my question." Jack did all the shopping and then he went to the café, but the first event didn't cause the second one; instead, the second event simply followed (sequentially) the first one.
Typically when we describe an event that follows a previous event without involving a cause-and-effect connection to that prior event, we use the word after, not when. Thus we would normally describe a one-off sequence of shopping + café visit this way:
Under these circumstances, the speaker's choice of when instead of after leads us to infer that the speaker has in mind a continuing pattern of behavior, rather than a one-time-only occurrence. We conclude that when means whenever.
To test this theory of how English speakers understand when, let's consider another example involving Jack the shopper, but this time let's tie his sequential actions more closely together. Here is the new example:
Here the double-bagging follows from the shopping much more closely than the café visit in the earlier example did. Consequently a hearer may be more inclined to interpret the sentence as describing a once-only event. Indeed, if we get rid of the troublesome word all, a hearer is extremely likely to interpret it that way:
The all muddies the waters by implying that more than one instance of shopping is involved, which makes the "on a particular occasion that" interpretation of when at least a little more difficult to sustain.
From this, it follows that the presence of all in the original example involving Jack's shopping and the subsequent café visit may have provided a subtle but important cue to hearers that the speaker was using when in the sense of "whenever." The presence of all, combined with the weak cause-and-effect relationship between shopping and café lounging, prompts a shift in our interpretation of when from the default "on a particular occasion that" to the less common alternative "on every occasion that."