Dealing with Character

In the recent weeks, Amy and I have been discussing character. She is a novelist and I am a short story writer. I don't get attached to my characters enough to deal much with their current character much less the character they might get in the future (i.e. Character Development).

This gap between us has left us to discuss characters as we see or interpret them.

For example, we saw a boat while we were in Crescent City. It was way out at sea and it was traveling North, toward Canada. As we discussed the ship, I decided that it was a drug running boat that transported cargo size shipments of Mexican marijuana to Canada. Aboard the Boat was Jack, a Canadian by birth, who found drug running to be a way to make good money for his mother who was suffering from various disabilities. Not only that but the money allowed him to use his boating skills to provide a natural substance opposed to being a whaler - a job that goes against his moral code because of the innocent slaughter of mating whales. However, on this particular trip, Jack was overly concerned about his chosen business. Jack's brother, Thomas, had recently died at the old ancient age of 16 - to a drug over dose. Jack was concerned about if he was doing the right thing....And that is as far as I have gotten. Amy and I occassionaly talk about Jack - but for the most part he is just on the boat because I don't know how to move his character along.

The same goes for another Jack. (Can you tell I like the name) I wrote about Jack the anti-hero a few months ago. Since then I have struggled to find ways to develop his character. I have more adventures in my head (Jack buys a rope to hang himself and instead lassoses a bank robber), but I am struggling to develop his character - why he is depressed? What will bring him out of his depression or dive him deeper? Why does he have such luck in not succeeding at such a simple task of ending his life? I don't know - mainly because I can't find it inmyself to develop Jack beyond that point.

Another Character I struggle with is the Amazing Drooling Boy. This is a name I have for one of my clients who constantly drools. On everything. I keep thinking I should develop an alter ego super hero for him but the more and more I try the more and more I'm stuck. So instead all I see is in my head - the amazing drooling boy.

Does anyone have any suggestions for developing characters?