Ok so at the end this is where Desmond met Penny.

In Flashes before your Eyes is said in a podcast that we should believe that the year is 1996..

The bottle of wine has the date 1995, but I have heard that is when it is barreled, if I am wrong please correct me..

It is also said in Flashes before your Eyes that Desmond and Penny have been to together for 2 years... Desmond tells Whitmore this when he is in the interview..

This means that when they met it was 1994 or earlier.. Does this sound correct to all of you.. I want to make a timeline for Desmond..

Thank 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: 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.