Someone said that in one of the preOscar interviews, Jake was asked how Jack really died in the movie, and he responded "Jack died the moment they couldn't be together".
This is one of the many messages I got from the movie....this idea of "waiting". I have this habit of "holding out" for the best situation....the best job, best vacation plans, best situation for relationships....but while waiting, the opportunity just passes by and it's way too too late. In this regard then, the person who was waiting too much time was not Jack, but Ennis.....and the tragedy of the whole story is that he lost that opportunity for happiness forever b/c he kept pushing it away.
Jack, on the other hand, is a dreamer.... and dreamers always have an allowance for "that one chance" that things will work out if they wait and try long enough. So this begs the question, which is of much larger scope, of whether or nor they were better off with the ways things were, or else, not meeting at all? Is it better to have loved and lost, or not to have loved at all? Was Jack better off seeing Ennis twice a year as opposed to not seeing him at all? Moments of fleeting bliss, vs no happiness ever? That's a tough one, but at the end, Jack came to realize that it really wasn't enough...there ain't never enough time, never enough.