Complex sentence: He contemplates his affection for a younger female student, Akashi, having in each case made a certain promise to her, usually of and within a romantic subtext, and the culmination of his dubious mission often conflicts with his interest in her in some way.
Split into simpler sentences: He contemplates his affection for a younger female student, Akashi, and makes promises to her, usually of and within a romantic subtext. The culmination of his dubious missions often conflict with his interest in her in some way.