Before the events of Kite Strings and 9/11, Bobby worked as a paper boy in New York. He developed a close friendship with the late Sarah Bohm, since she was the only one who seemed to care about his personal life. Wanting to get a GED, Sarah helped tutor him in Math for a few weeks prior to her death. Bobby also honored Sarah by naming his youngest child after her.
Bobby is first seen in the episode Kite Strings, mourning at Sarah Bohm's grave. Martin doesn't seem to know him and the two formerly introduce, but Jake distracts Martin before he can find out anything about Aresa. However, he is soon lead to Aresa's apartment building by Jake. During their talk, Bobby's history with Sarah is made clear. Bobby falsely accuses Martin and Sarah of having marital problems because she never wore her ring during the sessions (In reality, she stopped wearing her ring because she was getting it engraved). This accusation causes a small tussle between the men, which is broken up when Jake runs and locks himself up in a back room. Bobby's wife comes in, confused over the situation and Bobby fills her in on his relationship with Sarah. Martin manages to break into the room but Jake flees up the fire escape. Bobby has to rescue Jake because Martin feels that Jake only wants Bobby to catch him. When Bobby reaches the top, Jake loses his footing and almost falls to his death but is caught by Bobby. Martin then tells him he has finally repaid Sarah for her help. Before leaving, Bobby explains the possible significance of 9/5 - 9 1/2, that September 5th was the final session he and Sarah had. Bobby is shown with his wife and children at the end of the episode.
(To be added)