Rolen was born minutes after his twin sister Beia. Their parents, Reginald (human) and Branda (elf) Highwarden, were devoted parents, and took care to raise their children in a loving, supportive environment. Similarly, they strove to govern the small township of Oak Hill with compassion and grace, largely only intervening in its affairs when the people of the township asked for their aid and guidance.
Rolen and Beia were, at first glance, almost complete opposites. Where Beia was reserved, studious, and slow in her affections Rolen was glib, lackadaisical, and quick to befriend others. Despite these differences, the two were devoted to one another; not simply siblings but best friends. The bond between the two was further strengthened as they explored and developed the psionic powers that began to emerge during their childhood. Rolen has always been grateful that Beia, as the older of the two, would be the one to take charge of the families estates and duties...he knows he is ill-suited for such responsibilities.
Six months ago, Rolen woke to chaos. Fighting raged in the family's manse and on it's grounds. As he rushed from his room, he saw his sister, bound and gagged, being carried off from her room. He rushed to her aid...and the next thing he knew, he awoke to a pounding headache in the forest to the east of Oak Hill, his valet Donegal Oakeshotte peering at him anxiously. Donegal, ever loyal, had dragged him off during the confusion of the attack. The two returned to Oak Hill a week later, hoping to learn the identity of the usurpers and the fate of Rolen's parents and sister. They were not, however, discreet enough, and were soon attacked by unknown assailants while bedding down in a hayloft at the edges of the township.
The two managed to escape their attackers, but as they fled Donegal was hit by a crossbow bolt. Though it did not look to be a mortal wound, it soon festered, and only a week later Rolen was forced to bury his loyal friend. It was at this point Rolen decided to adopt Donegal's last name as a memorial (and, though he is loth to admit it, as a way to hide his true identity), and to travel to Evershoal, in hopes that he might be able to discover the identity of those responsible for his family's downfall and, he can only hope, the fate of his parents and sister.