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Caleb Henry Fairn is the eldest son of Harry Fairn and Miriam Wild, born January 12th, 1988 in the Fairn family home in Anaconda, Montana. Along with his three younger siblings Indio, Joy, and Jesse, he was raised by his single mother until the age of nine. He and his brothers were then raised by their father, moving to Columbia City, a suburb of Seattle, when he was 15. Due to Harry's inadequacies, Caleb took over the role of father figure to his brothers from a young age.

Caleb joined the US Coast Guard after high school, eventually achieving the rank of Petty Officer First Class. He receives a medical discharge at age 26 (03 Rhythm and Rhyme) and works as a military contractor. Despite being generally rock solid in his professional and personal life, a tragedy in the family leads him to struggle with excessive drinking at the age of 27 (starting in 08 Minor Key).

Upon the arrival of his half-sister Wynter in January 2013 (01 Little Sister Song), Caleb attempts to get custody of her. The family moves from Seattle to an old farmhouse on Tiger Mountain (near Issaquah), which he's slowly renovating.

Caleb is dating Bea Hayes in 01 Little Sister Song. In later books his dates include Nicole, Olivia, Ashley, and Kim Metez, and he reconnects with his high school sweetheart Anita Green.

Caleb plays bass in Rule212 and sings back-up vocals, as well as being the band manager. He took free piano lessons at school in Montana from third to eighth grade. He started playing guitar as a young teenager, then switched to bass when he was 15 so he and his brothers could form a band, the Fairn Boys.

In September 2015, Caleb meets his nephew Theo and takes care of him (09 Broken Strings).