A Bonnie to his Clyde. A woman who gets in to trouble almost as much as he does. Maybe they grew up in the same circle of friends. A blonde or red head would be great. Alternately, a good girl he grew up with who tires to put him back on the right track. Obviously, romantic line, but no harm if they just don't have the right chemistry! Extra points if two people want to bring in both for some added drama.