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Is it right to say

He was telling me that he will go on a vacation next week.

while recounting your experience?

Even though "he told me that he is going..." seems more appropriate, I would still like to know if the above mentioned expression sounds okay or not.

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Has he already went? –  jdstankosky Dec 19 '12 at 15:09
    
@jdstankosky Has he already did? :) Presumably you meant gone there. –  tchrist Dec 19 '12 at 15:20
    
@tchrist Undoubtedly, that is what I meant. I need caffeine. –  jdstankosky Dec 19 '12 at 15:22
    
What I'm trying to determine is if he still has yet to go, or if he has [or should have] already gone. The expression could sound correct or wrong, depending on the chronological context his schedule. –  jdstankosky Dec 19 '12 at 15:24
    
Although, the question reads completely differently now that I see the edits. was telling vs told is an entirely new question, isn't it? –  jdstankosky Dec 19 '12 at 15:28
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2 Answers

If you want to recount that something happened during the telling, you would use "He was telling me".

If you simply wanted to state the fact that he told you, the tense depends on whether he has already left on vacation.

So:

  • He was telling me that he was going on vacation, when the phone rang. (Past progressive: He may or may not have left on vacation).
  • He was telling me that he is going on vacation, when the phone rang. (Past progressive: He has not left on vacation).
  • He told me that he is going on vacation. (Simple past: He has not left on vacation as yet).
  • He told me that he was going on vacation. (Simple past: He may or may not have left to go on vacation).
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Lets say He has not left yet, and is planning to do it next week, so which one of telling or told I am supposed to use? –  Dude Dec 19 '12 at 16:12
    
So again - if something happened during the telling that you want to mention, you would use He was telling me that he is going on vacation when/and/while X happened. If you want to just want to state that he told you, then you would use He told me that he is going on vacation. –  mccannf Dec 19 '12 at 16:30
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The answer to your original question is that the time depends on he will go not He tells me. He told me he is going/ he will go means that he has not yet left: the commoner he told me he was going means only that he had not yet left when the conversation took place, leaving open the question whether he has gone by now.

The edited question is harder to answer: He told me or He was telling me would refer to a specific conversation. He is telling me or He tells me could be 'historic present'for the same thing, or He tells me could be non-specific, referring to what you gathered from a series of conversations in the past. (For completeness, he is telling me could also be normal present, but unless you are chatting to a colleague while composing your post, that's unlikely to be useful).

In normal conversation any of them are possible, since the distinctions are too fine to be useful.

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