His relationship with his aunt is shown to be relaxed and stable, her reaction to his disappearance from the farm is not seen as of yet.
Oscar is initially very disturbed by Ozpin's presence in his conscience. At first, Oscar is not receptive to Ozpin or his endeavors, deciding that Ozpin simply is not real and refusing to listen to him. However, over time, Ozpin convinces Oscar that he has a greater role to play and that he must leave for the City of Mistral. After making the decision to leave home, Oscar is much more amicable with Ozpin, though he shows to be distraught about the Headmaster doing something embarrassing and strengthening his mind and Aura. He has taken to speaking with Ozpin's consciousness within their merged soul, asking him questions, seeking guidance and knowledge, easing his mind in the process. Oscar, though frustrated, appears to appreciate the increased pace of his training, learning to quickly trust Ozpin's wisdom, taking in his muscle memory with natural talent. Oscar was taken aback by Ozpin's mercurial tone when revealing how he granted the Branwen twins the power to transform into corvids, finding the idea to be both surprising and rather bizarre.
Their relationship becomes strained in "Vault of the Spring Maiden", when Ozpin tells Oscar to run from Hazel Rainart but Oscar refuses, citing that Ozpin told him to fight. Even so, Oscar defends him from Hazel's accusations for Gretchen Rainart's death, on the grounds that she made a choice. However, Ozpin renders Oscar unconscious and forcibly takes control. In "Haven's Fate", Ozpin has Oscar pass on his message to Qrow to bring the Relic of Knowledge to Atlas.
Oscar awkwardly approaches Qrow after pressure from Ozpin. He asks for Ozpin's cane back and is very confused about the meaning of the interaction. On the other hand, in his elation in finding Ozpin's latest incarnation, Qrow becomes wildly drunk, furthering Oscar's unease regarding his unexpected subordinate. However, they later show a good relationship, such as when Qrow calms Team RNJR down as they surround him in amazement of him as Ozpin's reincarnation.
In "Vault of the Spring Maiden", Qrow displays a greater level of protectiveness towards Oscar in the heat of battle, diving in front of Oscar to shield him from Hazel's Dust-infused attacks, and keeping him out of harm's way as best he could.
After the battle has concluded in "Haven's Fate", Qrow tells an exhausted Oscar not to strain himself, and Oscar relays Ozpin's message to Qrow: get the Relic of Knowledge to Atlas. As the boy passes out, Qrow gently cushions his fall.
Upon meeting Ruby in "Welcome to Haven", Oscar is amazed at her silver eyes. In "Unforeseen Complications", Oscar blushes when he looks at her and she giggles at him, and they briefly exchange small talk about their unique circumstances. In "Lighting the Fire", Oscar spars with Ruby to learn hand-to-hand combat. After accidentally punching Ruby in the face, for which he is quick to apologize, Ozpin takes temporary control. Once training finishes, Ruby immediately tends to the exhausted Oscar, making sure he is okay. Later on, he receives encouragement from her and the rest of Team RNJR in finding his Semblance, likening Oscar to Jaune Arc who also has yet to discover his Semblance.
In "Necessary Sacrifice", Oscar admits his fear to Ruby of the inevitable battle they will have to face and bursts out his anger towards her because he does not understand how she appears to be calm and confident in the midst of the chaos surrounding her. However, he learns of her sorrow of losing her friends and her own fear of Salem and apologizes for his outburst, showing sympathy for her loss. As Ruby leaves, she assures him that despite the difficulty of the challenges ahead, the fact that he is there in Mistral shows he is braver than he thinks. Alone, Oscar admits to Ozpin that what they are facing is tough on her as well. Oscar appears to have a deep admiration for Ruby's take on life, her courage and her kindness in spite of all she has suffered through. Oscar even tries to emulate her kindness in his interactions with Hazel Rainart during their duel by offering him clarity and mercy.
In "Rest and Resolutions", after Ozpin's conversation with the Beacon students, Oscar finds himself touching Yang's shoulder, causing him to pull back in nervousness. Fortunately, Yang does not seem to mind and playfully laughs at his awkwardness.
In "Kuroyuri", Oscar seems uneasy when he first encounters Hazel. This is seen again in "The More the Merrier", when Hazel seals him and the others inside Haven Academy's Grand Hall. Then, when Hazel discovers Oscar is the new incarnation of Ozpin in "Vault of the Spring Maiden", he immediately sets his sights on him. Once Oscar learns of Hazel's sister, he tries reasoning with Hazel that Gretchen made a choice and that he would follow suit by fighting him.