Go or No Go

Back from vacation and I realize that I absolutely have less than 2 years to plan for my wedding!
I have discussed with him and we agreed that if it's possible, we planned to wed on 1st January 2010.

Had a talk with his Mom and she made me realize that I have to start planning the wedding from now because this is not going to be a small thing like the Engagement but something much bigger.
There is so much involved and these are the times when you have to make sure everything is perfect to every particular details.

Right now, I'm much concern of him. We are getting married, as in this is in serious talk, but is he well-prepared?
Mind wise, I think so. But money wise? I am not too sure.
He tells me that he has so much money. But every now and then, I see him struggling for it.
I'm scared. For him. For both of us. Is he not aware of our situation right now?
I tried telling him not to risk too much. But he is a man. No man listens.

If I decided to 'Go With The Flow' right now, does it make sense?