I'd forgotten that it bugged me back then, I suppose it was back in S2, but since Des and the time travel thing,. which I still don't get 100% I remembered questioning the timing.
Like I said it was the fact that Jack did so much in 2 years which made me question it, so was time different in the real world too??? More recently when Hurley heard that radio and mentioned about the different timeline, I think it was Glenn Miller?? Could this have been a big clue and we missed it!!!!
I'm sure we'll think of more examples if we think of the different flashback cross overs.
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