So tonight I rewatched Live Together Die Alone...

[We see Desmond in the hatch, holding a gun. He's finishes off a bottle of booze, and opens the Dickens book. A letter slips out. We hear a VO of Penelope reading the letter.]
PENELOPE: Dearest Des, I am writing this letter to you as you leave for prison. And I've hidden in the one place you would turn to in a moment of great desperation. I know you go away with the weight of what happened on your shoulders. And I know the only person who can ever take it off is you. Please don't give up, Des. Because all we really need to survive is one person who truly loves us. And you have her. I will wait for you. Always. I love you, Pen.
[Desmond sobs and throws the bottle.]

Remember when he reads this.. She said that she wrote it as he was leaving for prison. Well that would have to mean in Desmonds flashback they never broke up. Wouldn't it? Something just doesn't add up here for me if what all happened in Flashes Before Your Eyes took place in 1996.. Help what do you think?

__________________
Please don't give up, Des. Because all we really need to survive is one person who truly loves us. And you have her. I will wait for
you. Always. I love you, Pen

DESMOND: I love you, Penny. I've always loved you. I'm so sorry. I love you!
PENNY: I love you too.
DESMOND: I don't know where I am, but--
PENNY: I'll find you, Des--
DESMOND: --I promise--
PENNY: --no matter what--
DESMOND: --I'll come back to you--
PENNY: --I won't give up--
BOTH: I promise. I love you.