It had been twenty years since I [had] worked in TV

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1) It had been twenty years since I worked in TV
2) It had been tweny years since I had worked in TV

I understant both of the above are grammatical, but is there a difference in meaning?

To my understanding, 1 could mean:
It had been twenty years since I (last) worked in TV

And 2 could mean:
It had been twenty years since I used to work in TV

My reasoning for this is that if the sentences were in the present form the corresponding simple past and present perfect in the since clauses would indicate those meanings.

Is that the case or could the two be used interchangeably without any difference in meaning?
 
Could someone help with this?
 
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They mean the same thing to me.
 
1) It had been twenty years since I worked in TV
2) It had been tweny years since I had worked in TV

I understant both of the above are grammatical, but is there a difference in meaning?

To my understanding, 1 could mean:
It had been twenty years since I (last) worked in TV

And 2 could mean:
It had been twenty years since I used to work in TV

My reasoning for this is that if the sentences were in the present form the corresponding simple past and present perfect in the since clauses would indicate those meanings.
I think that you can indeed transpose the interpretation that a present-perfect "since"-clause would carry to a past-perfect context; however, I disagree with your interpretation of (2) on that construal. My understanding as a native speaker is that a present-perfect "since"-clause tends to carry the sense that the situation it expresses could naturally have been repeated in the time interval it denotes.

1a) It has been twenty years since I worked in TV.​
2a) It has been twenty years since I have worked in TV.​
Sentence (1a) simply indicates that the speaker was working in TV twenty years ago and stopped, twenty years having elapsed between then and now. Sentence (2a) indicates the same thing but implies that the speaker might naturally have worked in TV in the intervening time interval. For whatever reason, the speaker was not called or inspired to do so. You can have the same type of interpretation with (2), in the past-perfect context.

Of course, it is also possible to interpret (2) as meaning exactly the same thing as (1), but in that case it is not being treated as the transposition of the present perfect to a past-perfect context. On the interpretation according to which (1) and (2) have the same meaning, the past perfect carries "past within the past" meaning in both the main clause and the "since"-clause. To illustrate the differences, let's let the "since"-clause denote a situation that can only occur once:

3) It has been twenty years since he died.​
4) *It has been twenty years since he has died.​
5) It had been twenty years since he died.​
6) It had been twenty years since he had died.​
Although (4) is ungrammatical, (6) is not, because it is possible to interpret the "since"-clause in such a way that does not correspond to the present-perfect interpretation. The mind of the native speaker naturally not even thinking of the ungrammatical interpretation, we naturally take the past perfect in the "since"-clause of (6) as carrying mere "past in the past" meaning.
 
2a) It has been twenty years since I have worked in TV.​

Sentence (2a) indicates the same thing but implies that the speaker might naturally have worked in TV in the intervening time interval. For whatever reason, the speaker was not called or inspired to do so
I think that is stretching interpretation too far. I see no suggestion at all of that idea.
 
Sentence (2a) indicates the same thing but implies that the speaker might naturally have worked in TV in the intervening time interval.

Yes, I think that's probably right. If there is some aspect of meaning that the present perfect brings that the past simple doesn't, it must be a relevance connection of some kind between past and present. I see this relevance as being about life experience, or lack thereof; sentence (2a) could be saying 'I haven't had any experience of working here in the last twenty years', and this logically includes the possibility that it could have been otherwise. That's also why (4) is wrong, as you say.

There are other ways to interpret the relevance too, I think. I also imagine that (2a) could be uttered by someone who is just returning to working in TV after twenty years—it could be saying 'I haven't done this for twenty years'.

we naturally take the past perfect in the "since"-clause of (6) as carrying mere "past in the past" meaning.

I agree here too. The past perfect is just sequencing events. If there were meant any extra aspectual meaning, it would get lost.
 
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I think that is stretching interpretation too far. I see o suggestion at all of that idea.
Just to clarify, I don't mean that the present perfect in the "since"-clause grammatically/aspectually conveys that the speaker was not called or inspired to work in the TV industry in the intervening time interval; I mean only that it conveys the idea of potential but unrealized repetition of working-in-the-TV-industry events in the intervening time interval. The part about lack of inspiration or being called on was my attempt to offer possible explanations for lack of repetition.

My interpretation of such present-perfect "since"-clauses is based not only on my natural sense of the meaning but on the confirmation I once found for it in a good tense book by Renaat Declerk. I have just found the relevant passage again:

"It is interesting to note that a condition for the use of the present perfect in the since-clause is that the situation referred to is potentially repeatable: the sentence implies both that the situation referred to in the since-clause actualized a certain time ago and that it could have actualized again at any time (or at various times) in the pre-present period following its actualization . . . . Compare: . . .
It's (been) five years since I've seen him. (implies 'I haven't seen him for five years'. The situation is 'repeatable' in the sence that it could have actualized (once or several times in the specified pre-present period.)
It's (been) five years since I (saw / *have seen) him on the 20th anniversary of his marriage. (The situation of seeing him on the 20th anniversary of his marriage is not repeatable.)
It's (been) five years since (I last saw him / *I've last seen him). (Last blocks the idea of repeatability.)"
- Declerck, Renaat. The Grammar of the English Verb Phrase. Volume 1: The Grammar of the English Tense System: A Comprehensive Analysis, pages 263-264. Mouton de Gruyter, 2006.
 
in a good tense book by Renaat Declerk.
I accept that the book is interesting, but I don't agree about the 'good'.

Declerck has an unfortunate tendency to present opinion as though it is fact. One example: on page 314, he writes:

Compare I have bottled the chutney which is indefinite, and I have been bottling chutney since 9 o' clock, which is continuative. The fomer implicates the direct result 'The chutney is bottled'. The latter is used to refer to such indirect results as 'The house smells of tomato chutney' or 'That's why I am tired', but will not be used to suggest 'The chutney is bottled now'.

The will towards the end is opinion, backed by nothing but Declerck's self-confidence.

Back to page 264 :
It's (been) five years since I've seen him. (implies 'I haven't seen him for five years'. The situation is 'repeatable' in the sense that it could have actualized (once or several times in the specified pre-present period.)

The words I have underlined are, once again, unsupported opinion.
 
I accept that the book is interesting, but I don't agree about the 'good'.
Well, it does have a few typos, but I find Declerck's coverage of tense and aspect, overall, to be astonishingly brilliant and clear, and I am very sorry to learn that he will not be completing the other volumes projected for the series. I had a brief messaging interaction with Declerck about that roughly ten years ago when I requested a paper of his on something not related to the tenses, and he indicated that, on account of his getting on in years, he would not be able to complete the project.
Declerck has an unfortunate tendency to present opinion as though it is fact. One example: on page 314, he writes:

Compare I have bottled the chutney which is indefinite, and I have been bottling chutney since 9 o' clock, which is continuative. The fomer implicates the direct result 'The chutney is bottled'. The latter is used to refer to such indirect results as 'The house smells of tomato chutney' or 'That's why I am tired', but will not be used to suggest 'The chutney is bottled now'.

The will towards the end is opinion, backed by nothing but Declerck's self-confidence.
I wonder if there's a typo in the example sentence I have been bottling chutney since 9 o'clock. Given that the other example, I have bottled the chutney, contains the before chutney, one would expect the to appear before chutney in the related example. If the were used there, his point would follow, I think. From the statement I been bottling the chutney since 9 o'clock, it would be unreasonable to infer that the chutney (all the chutney; the contextually given quantity of chutney) is now bottled.
Back to page 264 :It's (been) five years since I've seen him. (implies 'I haven't seen him for five years'. The situation is 'repeatable' in the sense that it could have actualized (once or several times in the specified pre-present period.)

The words I have underlined are, once again, unsupported opinion.
So, do you not agree with the point that these present-perfect since-clauses aspectually suggest potential but unrealized occurrences of the event in the time period they pick out? (Incidentally, it may be worthwhile to observe that extra-grammatical empirical matters are beside the point here. For example, if the speaker has not seen the referent of him for five years because he [the speaker] has been in prison for those five years, the aspectual suggestiveness of potential but unrealized repetition would still be there, at least for Declerck and me; at best, one could say that it would have been more felicitous, in such a context, for the speaker to use the simple past in the since-clause: It has been five years since I [last] saw him.) If so, how would you account for the ungrammaticality of a sentence like (ii) below?

(i) It's been over twenty years since the original World Trade Center building was destroyed.​
(ii) *It's been over twenty years since the original World Trade Center building has been destroyed.​
 
I think. From the statement I been bottling the chutney since 9 o'clock, it would be unreasonable to infer that the chutney (all the chutney; the contextually given quantity of chutney) is now bottled.
I don't agree.
 
I don't agree.
I think a type of test sometimes used in pragmatics might be of use here. Consider the following contrast:

a) # I have bottled the chutney, and now the chutney is all bottled.
b) I have been bottling the chutney since 9 o'clock, and now the chutney is all bottled.

I think most people would find the second independent clause of (a) hideously infelicitous, insofar as it redundantly asserts something already entailed by the first independent clause. The same does not seem to hold true of (b) at all.
 
The same does not seem to hold true of (b) at all.
I agree.

However, that does not necessarily mean that
From the statement I have been bottling the chutney since 9 o'clock, it would be unreasonable to infer that the chutney (all the chutney; the contextually given quantity of chutney) is now bottled.
 
One cannot logically 'infer' that the chutney is bottled or unbottled from the uncontextualised words alone, so yes it would be unreasonable in that regard.
 

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