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In last week's Official LOST Podcast, Damon Lindelof attempted to explain what happened to Desmond as follows:
Yeah, I guess it wasn't really quite a flashback in the conventional sense... The reality is, this is more the experience he had when he turned the fail safe key, and obviously as evidenced by future memories that he's having during his flashback, for the first time in the history of the show we actually allowed a character to have an opportunity to make a different choice than they made before, and Desmond doesn't. He's course-corrected by a certain mysterious older lady in a ring shop...

Did it really happen? Yeah, I think it really happened. I mean, you know, one of the things we try very rarely to do on the show is to play something as only having been imagined or dreamed, and I would say that in the global sense of things that Desmond went back and in the year 1996 actually had that experience. Now, I would venture to guess that in future flashbacks of Desmond's that they would be treated as traditional flashbacks where he doesn't really have any awareness of his destiny...