Honestly Ben by Bill Konigsberg
Ben Carver returns for the spring semester at the exclusive Natick School in Massachusetts determined to put his relationship with Rafe Goldberg behind him and concentrate on his grades and the award that will mean a full scholarship — but Rafe is still there, there is a girl named Hannah whom he meets in the library, and behind it all is his relationship with his distant, but demanding father.
Review from School Library Journal Starred:
Ben Carver works hard trying to please his friends, his teammates, his teachers, and, most important, his father. Barely keeping up with his classwork, extracurricular activities, and friendships, Ben wonders if he does all of these things for himself or just to placate those around him. He grapples with staying true to himself, even if he isn't sure who that self is yet. This follow-up to Openly Straight is told from Ben's perspective as a scholarship student living among privileged classmates as well as a teen wrestling with the consequences of living by other people's expectations. Well-rounded characters take readers from serious, thoughtful discussions to typical teen pranks with ease. A boarding school story along the lines of Andrew Smith's Winger, this is equal parts serious and funny as it addresses homophobia, hazing rituals, and cheating while also delighting readers with a slice-of-life tale set at a private academy.