Harold Montgomery is Sam's biological father and Brianna & Gabriella's stepfather. He was a great father to Sam. But he was very foolish to marry Fiona. He used to own Hal's Diner. When Hal was killed in the Northridge Earthquake, Fiona got the diner. Sam thought Hal didn't leave a will, but he hid it in Sam's childhood fairy tale book and only Fiona knew about it since she signed the witness line of the will. Though she didn't say anything about it to anyone.. Sam started owning the diner after finding his will. Hal is mentioned several times when Sam was in her teens. He is portrayed by Whip Hubley.
- Name: Harold Montgomery
- Physical Appearance: Tall, brown-haired handsome man
- Personality: Kind, loving
- Relatives: Unnamed first wife, Sam Montgomery (daughter), Fiona (second wife/widow), Brianna (stepdaughter), Gabriella (stepdaughter)
- Occupation: Owner of Hal's Diner
- Other Names: Hal
- Fate: Died during the Northridge Earthquake