Yea, but we know Jack has started drinking OJ and vodka at that time too.. But after the trial Jack and Kate are together when Jack goes to visite Hurley and he is much worse.. This leads me to believe that when Hurley and Jack played Horse it was just before the end of the trial or right after before he decided to live with Kate and Aaron. Kate does make the comment that she got Jack the new razor and he asks what ya don't like the stubble? So I am thinking that the game of horse was before that but maybe not that much before..

__________________
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.