Rupert is a fairly major character who appears in all of the episodes in the first season (so far as of Episode 08). Later at Castle Leoch, Angus and Rupert were tasked to follow Claire around and keep an eye on her (supposedly reporting her actions back to Dougal). Rupert is a cheerful, friendly sort of fellow. When Claire confronts him about following her, he told her that he is but the "eyes" that will follow her until the head (Dougal) says otherwise. In the S01-E05 Episode Rent, Rupert was bragging about having two women in his bed fighting over him, and Claire piped up with "More like the left hand being jealous of the right", and that got everyone laughing. He said that he'd never heard a woman tell a joke before. On Claire and Jamie's wedding night, Rupert and Angus barged in on the couple, at Dougal's command, to see if they'd consummated the marriage. After they did, and Jamie went downstairs for food, Rupert said to him lewdly, "How was yer first time, Jamie? Did ye bleed?". Claire asked Jamie if he was related to them, and Jamie answered, "Rupert only, he's a distant cousin". Rupert was the person in the TV show who paid for Claire's wedding ring in the S01-E07 Episode The Wedding, and then in the next S01-E08 Episode Both Sides Now he was telling the "Water Horse" story very calmly with everyone gathered around the campfire when the Grants attacked.