Masayoshi Umehara is a secondary character in Amagami SS and Amagami SS+ plus. He is Junichi Tachibana's childhood best friend and a classmate in their second year at Kibitou High School. Umehara is a kind and outgoing person with a somewhat frivolous but genuinely good-natured personality. He has a strong interest in Japanese idols and frequently purchases photobooks of them, which he shares with Junichi. His family runs a sushi shop, and he plans to inherit it in the future. Umehara deeply respects Junichi, often addressing him as "boss," and is consistently supportive of him across all story arcs. He is also close friends with Kaoru Tanamachi and serves as a reliable confidant to the main group. In the series, Umehara plays a key role as the loyal friend who helps Junichi navigate romantic pursuits and personal setbacks, even going as far as to misdirect others to protect Junichi's private moments. His own development is subtle, primarily shown through his unwavering loyalty and his occasional moments of wistfulness about his own romantic prospects. While he has no extraordinary abilities, his keen knowledge of popular culture and his knack for offering timely advice make him a dependable presence. Umehara's most notable trait is his steadfast friendship, which provides emotional grounding for Junichi throughout the anime.