Here’s a fun thing you learn when you study literature: the western canon is not universally beloved. Those books are not the Truth any more than the New York Post is skilled journalism. The main reason they’re held in such high esteem is because they were written by boring white dudes with rage fantasies and boring white dudes with rage fantasies also happen to be largely in charge of deciding which books are deemed classics and taught forever in the American school system.
So if your boyfriend tells you he loves Kerouac then you tell your boyfriend Kerouac was a fucking second rate hack who wrote Beat style because he didn’t have the skill or talent to write any other way, which is probably also why he just copied every adolescent male wanderlust story since the beginning of time. That shit’s derivative and boring.