Parents are Giovanni and Francesca. Older brother Fiorentino (by two years); younger sister Mirabella (by five years). Giovanni is a gondolier in Sel-Kai. Fiorentino is following in his father's footsteps. Francesca didn't want either Giuseppe or Mirabella to go into the rough trade of boatmen, which the whole family has certainly had to occassionally deal with.
Nevertheless, at a young age, Giuseppe started helping his father with his gondola. At first it was repairs on his father's boat; later, while his father was busy working the canals, Giuseppe would help with whatever of his father's friends needed help, from the construction, repair, renovation, outfitting, etc, of gondolas. Giuseppe met many other gondoliers this way, and didn't particularly wish to be a gondolier due to the monotony of the work.
Two years ago, Giuseppe was with his father when they were walking by the CBSK. The owner, Divad, and the bartender/bouncer, Tad Konteran, were hanging a new awning. As they walked by, the ladder that Tad was standing on collapsed. Tad broke his leg, and Giuseppe and Giovanni went to help. Divad was out a bartender, and Giuseppe offered to help for the night. By week's end, Giuseppe was a regular fixture in the place and rather liked the work, and Giuseppe became a regular worker there. Meals, a pallet to sleep on, and a little money in exchange for work. Not surprisingly, his parents were relieved to find that he had found regular work for himself.
Divad couldn't keep "Giovanni" and "Giuseppe" straight in his head, so he just took to calling Giuseppe "Jack". A few people at the CBSK might remember Giuseppe's real name, but most everyone knows him as Jack.
Jack occassionally goes back home (notably during festival meals), but it's more likely that his father will come by to visit, rather than Jack going home to visit. This happens about once every three weeks or so. Francesca and Mirabella are usually too busy (or tired from working) to visit; Fiorentino is either busy or off with his own friends. Giovanni knows that he can easily guilt-trip his son to come visit his mother and siblings, but rarely does so, knowing that Jack is trying to establish himself as his own man.
Tad still works at the CBSK, and helps Jack learn people's names and gives him pointers on martial arts: how to dodge a drunk patron, how to punch their lights out, and if necessary, how to use a sword to defend himself. The lattermost has been mostly a romantic hobby of Jack's that he's found some natural aptitude for -- not that he has time to train. Jack also takes mental notes on Divad's deftness in rumor-mongering and dealing with customers and visitors.
Jack's plan is to eventually find his own job as bartender/bouncer at another inn, since Tad is not going anywhere. But for now, Jack doesn't have any particular need for more money, still has a lot to learn from both Tad and Divad, and has a lot of friends at the CBSK.
Between using up his savings and borrowing a bit from his parents and Divad, Guiseppe managed to enroll in the Mentalism school in Sel-Kai. He stayed only for 4 months before being forced to drop out due to lack of funds. He made phenomenal progress while at the college, but usually found that he suffered from occassional headaches (oftentimes quite debilitating), especially at the beginning. His mentors assured him that the headaches would eventually pass, which they have, although Jack developed a habit for drinking, which usually takes the edge off his headaches. Even today, if Jack exerts himself greatly via spellcasting, his headaches return.
No woman is currently in Jack's life. He has a large group of friends and occassionally gets lucky (typically with bored sailor women who he rarely sees). By and large, Jack enjoys being unattached.
Perhaps because his father's a gondolier or perhaps because of the memories of the two or three sailor women who look him up when they're in town, Jack often spends his free time on the docks. Lately, he's been trying to get to know the proprietors of various taverns better, thinking ahead to a better job. He's visited friendly and not-so-friendly taverns. He doesn't particularly enjoy some of the seedier places, but he does get a rush from the practice of mingling with the various seedy types. His only contact with the Collegium is through other students at the CBSK. Jack doesn't particularly wish to turn into a Collegium groupie, nor turn bitter about not having the money to pursue his studies.
Given a large amount of money (which he occassionally gets from a good week of tips), Jack's first impulse is to save it to return to the Collegium. This impulse is often modulated by any woman who might be occupying his thoughts, so he's often gotten an accessory for a woman. (This is one reason why he has a large number of female friends. Not that he necessarily has ulterior designs on them all, just as he's not dumb enough to be used by these same women.) An enameled pin, a scarf, some ribbons, even just a swath of nice cloth are all gifts he's gotten in the past. Jack occasionally gets nice clothes for himself, but given that Jack's job involves getting all sorts of ales, food, soot, mud, and whatnot splattered on him, he usually avoids the temptation to actually buy any new clothes unless he needs it. The only remarkable thing about his clothes is that they are almost always not in bad condition. He does own some nice clothes that he wears on free days or when trying to impress someone. The second impulse for spending money is on excellent food and drink.
Insofar as money, he long ago paid off his loan from his father and from Divad for his first few terms at the Collegium, and is now trying to save up more so that he can study at the Collegium full-time.