(Sean O'Neal) – Clarissa's best friend and confidant. Generally more optimistic and upbeat than she is, he often asks "What's the worst that can happen?" He is perhaps best known for entering her second-story bedroom with a ladder after a distinctive guitar chord plays followed by Clarissa's "Hi, Sam" greeting. Creator Mitchell Kriegman explained that Sam entering the house through Clarissa's bedroom window was "a way to get him into her room [...] and start interacting faster" as well as keeping their relationship non-sexual. He is smart and polite and enjoys skateboarding. His parents are divorced (mentioned in the pilot) and it is mentioned early on that his mother left his father to join a Roller derby. Sam's father works as a sports journalist and later gives Clarissa the opportunity to complete some work experience with him. In the unaired Pilot, he was played by Darren E. Higgins. Recurring Aunt Mafalda (Heather MacRae) – Clarissa and Ferguson's aunt from Canada whom Clarissa dislikes and tries to get rid of in two episodes in the first two seasons. Clifford Spleenhurfer (David Eck) – Originally a bully who harassed Ferguson in Season 1, he developed a crush on Clarissa when she stood up to him. She later misses his affections in Season 2, and they begin a relationship which ends in Season 4. He appeared in a total of five episodes, the most of any recurring character. His defining characteristic was a big appetite, much to Marshall's annoyance. Dr. Festerspoon (Bob Noble) – The family doctor, who appears in two episodes in seasons 1 and 4. Hillary O'Keefe (Sara Burkhardt) – Clarissa's friend from Thomas Tupper High, who appears in four episodes in seasons 2 and 3. Deborah "Debbie" Anders (Susan Greenhill) – Sam's estranged mother who is often on the road with a traveling women's Roller derby team. She appears in a third-season episode where she tries to take custody of Sam and make him move to Seattle and again in the fourth season when she stays with the Darlings and becomes a burden. Olivia DuPris (Nicole Leach) – Another one of Clarissa's friends from high school, who appears in seasons 4 and 5. The Soapersteins – The Darlings' mostly unseen next-door neighbors, referred to continually throughout the series. The mother and daughter appear once in season 4, and the family's dog appears in season 5. Notable guest appearances These are