Brian Matthews is one of the recurring characters of Desperate Schoolboys. Brian is introduced as the latest in a long line of romantic conquests by Annie Hadland, which leads her son to show unwillingness to accept Brian as part of his life. However, as Joe grows to learn, Brian is a kind man who might just restore both Annie's and Joe's faith in having a male role model around.
Annie tells Joe that she has a new boyfriend that she'd like him to meet over dinner, Joe seems unhappy about this, but gives in and agrees. That night, Joe, Annie and the latter's new boyfriend, Brian, exchange and awkward dinner. When they sit down after, Joe tries to scare the boyfriend off by telling him of how many guys Annie has brought home in the past, however, Brian makes it clear that he's not budging and that Joe will just have to accept this. ("Wanting for Everything") We see that Joe has tried numerously to sabotage Brian and his mother's relationship with a string of childish pranks. Later, Brian approaches Joe when he's printing off his Dr. Sonya posters and takes an interest, however, Joe mistakes this for mockery and tells him to go away. Brian returns later and offers to help Joe take Dr. Sonya down, believing his pedophile story. ("Binding Affairs")
Joe receives a call telling him to meet the caller by the window of Dr. Reynolds' office at 7:00 P.M. Joe is confused and hangs up. That night, Joe sneaks into Reynolds' office, but the shrink catches him. Joe locks himself inside and waits for his mystery rescuer to arrive. Dr. Reynolds soon manages to break the door down as Brian arrives, he helps Joe out the window and drives him home, not agreeing with Annie's wishes and still believing the boy about Dr. Sonya. ("When God's Back is Turned") Dr. Reynolds calls Dr. Sonya, telling him that Joe escaped, much to the former's dismay. Joe makes Dr. Sonya admit to his pedophilia before revealing that he got the conversation on tape, via Brian. They report Sonya to the police, however, a policemen tells Joe that the shrink has fled. Joe is then approached by Annie who apologizes for sending him to the clinic. ("It Just Never Ends") Annie leaves town for a weekend away with Brian, leaving Joe home alone. ("A Spot of Bother")