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I watched it recently.. I have watched it many times.. Mrs. Hawking is telling Desmond that he doesn't marry Penny he walks right out the door.. While the small fact that he did buy the ring the second time around didn't change the fact that he still didn't marry Penny.. He did join the Military.. He did end up on the island..

I think that he did live out the path that was laid out for him even though in Flashes he did have the chance to change everything.. Remember in the bar the second time when he realizes he isn't crazy he had the wrong day.. He tells the bartender that he thinks he made the biggest mistake of his life and he doesn't think its the first time..

The big difference if you ask me about the "Constant" and "Flashes" is the fact that Desmond knows that he is time/mind traveling in the Constant, in Flashes he calls it Déjà vu