This is a response to Vol 16 Suzanne 9 ("And Yet More Suffering")...
Your story-telling skill comes across beautifully and you painted an interesting portrait of Jimmy. Of course I can think of a few guys that resemble him and how they would act in this kind of situation.
Little question that a different job would have molded him differently, just as would the nonexistence of the Italian background that you hinted at, or the effect of a rigid mother and father might have had or of a multitude of small things that would add up and change his viewpoint and hence his actions. There is always a strong possibity that he might change - from hanging out at the bar and being center of interest and admired hero of the others there - to a "good husband" with a trace of spicy unpredictibility and mystery. In fact I place that probability high over a 10 year period.
The most interesting and key part of the story is his telling you that "he never made dates" and you would have to come to the bar if you were interested.
How about this idea? The guy is married, but spends most of his evenings hanging out with a gang of buddies (mostly from high school). He is the "Sam Malone" of the group, being the best looking or best talker or both. To keep up his reputation he needs to demonstrate that he is a macho-type ladies man. This is proved by the appearence of a unfamiliar and attractive female looking for him, say about once a month. However, to keep the situation from becoming a problem, the guys in the bar are primed to tell stories that will scare off the sensuous but non-Italian woman, allowing him to keep his reputation but not running any real risk of a serious affair. The "trapped by the mafia" touch is great too.
There are lots of other possibilities but that seems the most consistant from the given information.
Because he is a garbage man, he probably feels the need to build up the admiration of his friends. It also puts him into the lower middle class social bracket and makes the neighborhood bar scene in the evening more desirable. Put him in an office, white shirt and tie and a group of middle class friends, and in a few years you wouldn't be able to tell him from the other (now becoming extinct) yuppies.