Joe Hadland is one of the main protagonists of Desperate Schoolboys, and thus his family is central to the series and its stories.
- Joe Hadland - A tempermental schoolboy with a bad relationship with his mother.
- Annie Hadland - Joe's young mother who is known as the town slut for her many sexual encounters.
- Matthew Hadland - Joe's estranged father. Matthew is a thief with a past of illicit behavior, whom his ex-wife Annie tried to protect their son from.
- Brian Matthews - Annie's newest boyfriend who was once estranged with Joe, but they soon grew a family like bond.
- Katie Vaala - Joe's girlfriend as of season four.
- Silvia Mayfair - Joe's evil ex-girlfriend who has taken many identities over the years in order to escape from one person to the next.
- Dr. Brad Sonya - Joe's former theropist who was revealed to be a pedophile with pictures of half naked kids.