Alan was born to Romny Orben and his wife Shannyn Roxton. His father died in Robert's rebellion and his mother died in childbirth when he was 5 years old; it is unknown what happened to his infant half-sibling. Lord Randyll Tarly brought the boy to Horn Hill soon after, and decided to foster the boy, intending to restore House Orben with it. Alan and Lord Tarly's son Samwell would become good friends. He soon said goodbye to Samwell when he left Horn Hill to join the Night's Watch, and became an older brother of sorts with Lord Tarly's new heir, Dickon, until he began squiring for a knight in Lord Tarly's service. He began his training as a knight just before the War of the Five King's started.
by 300 AL he was finally knighted at the age of 18. When he returned to Horn Hill, he was married to Lord Tarly's neice Marna straight away. Alan and his new wife headed for the Floxlake the following morning, and as a wedding gift from Lord Tarly, they were granted 2,000 armed men and servants to escort and finally serve them at their castle. Striking a deal with the minor houses from the Reach and the Westerlands, Small towns were build all around the castle.
A year later his wife gave birth to his first born son and heir, Randyll Orben, named after Lord Tarly.
Alan is delighted when his wife gives birth to their second son, Lorent. He receives many letters from Lord Tarly concerning his management with the new towns built beside the Floxlake. Alan proves valiantly that he could manage his people. Lord Tarly sends Arrin Hunt to be fostered at the Floxlake, with the promise that he would squire for Alan when he came of age.
Alan receives a raven from Lord Tarly, calling his banners to aid House Lannister against the Tyrells.