Ryckon is a robust young man with a stout and muscular build, giving off an impression of strength that is somewhat belied by the awkward manner in which he carries himself. He has a heart-shaped face with vaguely rough features. His short but thick and unkempt curly hair is chestnut-colored, as are the sparse hairs on his chin and upper lip, which may one day grow into a beard and mustache but for now remain as a telltale sign of his youth, and his bushy eyebrows, which have a habit of raising often. His eyes are dark brown and have a keen glint to them, often combined with nervous energy.
Most people will see Ryckon at court, and so most people will see the side of him that comes out at court. In social situations, Ryckon is nervous, uncomfortable in his own skin, and prone to stammering, particularly if those social situations involve women. While he can grow more comfortable in a conversation given time, a proper subject, and familiarity with the others involved, the first impression that most people will get of Ryckon is an awkward boy stumbling over himself trying to be polite. This, however, does not hold true in battle situations. Ryckon is known for being highly skilled in combat, and combat is when he seems most at ease. It is rare to hear a stammer from Ryckon out in the Kingswood, and slightly less rare for him to stammer to a sparring partner. Despite being called “the Ruthless” by some for his tourney exploits he has a strong sense of chivalry and honor inherited from his father, which comes into conflict with his uneasiness around ladies and his fledgling skills of manipulating other people. Ryckon has a bright mind and enjoys reading, but his training usually takes precedence over such pursuits.
In 147 AC, Ryckon was born to, and named for, Ser Ryck Westerling, a famous knight, and Maelane Swyft. His house was an old, prestigious, and increasingly impoverished one, but Ryck made a good living through the ransoms and awards from the tourneys he so frequently excelled at. The flip side of this was that he was often away from home. Ryckon did not know him as well as he could have, but idolized him nonetheless, and aspired to live up to all of the tales of greatness that he heard.
Since childhood, Ryckon was very strong for his age and he had a natural aptitude for combat, in addition to a bright and eager mind. Seeking to bring honor to their house by continuing their tradition of great knights, his family encouraged his martial talents rather than his mental ones, and he was squired off to his great-uncle Lord Joseth Smallwood of Acorn Hall, known as Oakshanks.
When war broke out in Dorne, Joseth went to fight and Ryckon went along with him, marching in the host of the Riverlands. The squire saw the war as a chivalrous adventure at first, but that soon changed as he killed men and saw men die. He seemed to adapt quickly, though, and he even appreciated the chance to train his skills in a real environment.
In 161, Ser Ryck was killed at the Battle of Godsgrace, and Ryckon fell into a deep mourning. Lord Joseth allowed him to grieve rather than making him attend the following parley—and was himself killed after a failed charge trying to save King Daeron from the treacherous Dornish. Now without a master, Ryckon was sent home with his father’s bones, a changed boy, not nearly as easy-going or self-assured as he had once been. He was back at the Crag for only a short time before his family sent him to serve as a page in Casterly Rock, hoping to find a new knight for him there. A year later, he found one, in the form of Ser Farin Prester, who was returning to King’s Landing after his marriage to Aurana Buckler in Feastfires, and he followed them to the capital of the realm, along with Urron and Katla Greyjoy.
Ryckon became a member of the court in King’s Landing. He frequently interacted with the other nobles, and good degree of social awkwardness became apparent, especially around the fairer sex. As a squire, he continued his training to be a knight. He improved his martial skills both in combat, resulting in his victory over his cousin Humfrey in the Melee of Honor, as well as other admirable performances in tourneys that fell short of victory due to having less skill with the lance than with the mace, and in the art of war. He developed his social skills as well and worked with Ser Farin to improve his position at court. Due to his master’s position in the Kingswood Company they frequently fought against the bandits of the forest. On one notable occasion Farin conducted a successful suicide charge to burn a bandit holdfast, of which Ryckon was part, and on another Ryckon led a small group of men to free the whores Rogan Turncloak had enslaved, directly after the death of Bors Breakhelm.
A scandal emerged as Humfrey, heir to the Crag, made it clear that he wished to end his lucrative betrothal to Jannia Tully, and then killed the hedge knight Lying Lem, formerly in the Westerlings’ service, at a tourney. As the court made its way to Riverrun for that marriage and another, Lord Daric ended the betrothal, disowned Humfrey, forbade Ryckon to participate in a melee being held, and was fined the obscene sum of 2,000 dragons by Lady Tully. The disgrace only encouraged Ryckon to try to be a shining example of the honor of House Westerling.
At the tourney celebrating the other wedding in Riverrun, the ancient feud between Houses Bracken and Blackwood erupted once again and soon elevated into war. Farin sided with the Brackens, his cousins, and took Ryckon with him. In the Battle of Pennytree, Ryckon saved Farin’s life from a foe, and then, as the tide of battle began to turn against the Brackens, fought and defeated the great warrior Balian Blackwood, saving the Bracken retreat. For his actions, Farin knighted him at the early age of 16 two days later, at Stone Hedge.