The Halls Of St. Matthew's

It's 1959 in Massachusetts and fourteen year old Benjamin Perry is starting his first year at St. Matthew's Boys Academy, a prestigious Catholic boarding school. The large campus features towering stone buildings arranged around a spacious grassy courtyard and a shimmering fountain, including the dormitory, chapel, the main school building with its classrooms and administration offices, the sports hall, and the dining hall building. Under the watchful eye of the strict Headmaster, Mr. Aston, and demanding professors, Benjamin feels the crushing weight of his parents' expectations, especially his father's demand that he be at the top of his class for all four years and earn a spot at Harvard. But amidst the pressure and old traditions, Benjamin finds a much-needed break in his roommate Jack Reece and Jack's football teammates, David Flossom, Charlie Kelt, and Simon McGivins, who all share the same dorm floor and have classes together. Together, they help Benjamin discover calm and camaraderie in a world where excellence is expected but friendship becomes his true lifeline.

(The timeline is gonna jump through months to fit in the whole school year and fun moments mixed with hard times.)