This paper focuses on similarities between two literary characters: Śvetaketu from the Upaniṣads and Ambaṭṭha from the Dīgha Nikāya. By comparing these two characters, as well as the characters with whom they interact, I will suggest that these literary figures from competing religious traditions appear in different presentations of the same story. Both Śvetaketu and Ambaṭṭha are depicted as brahmin students who are young and arrogant as they approach the domain of a non-brahmin. In the case of Śvetaketu, he is rude in his encounter with the king; whereas Ambaṭṭha is disrespectful to the Buddha. In both cases the young brahmin leaves the non-brahmin after being defeated in debate, without having learned from him an important teaching. Finally, both brahmins are replaced by their teachers, who in contrast are more refined and humble. As I will demonstrate, these similarities, along with other shared literary features between these stories, shed new light on the relationship between the Brahmanical and Buddhist narrative traditions.