Kim attended Starfleet Academy from 2366 to 2370. (VOY: "Non Sequitur") During his last year at the Academy, he had a roommate named James Mooney MacAllister, who studied excessively, even at night. This forced Kim to wear an eye mask to help sleep, reminding him of his mother's womb, of which he still retained memories. He retained the practice of wearing the mask at night throughout his Voyager assignment. McAllister helped Kim in his fourth year Quantum Chemistry class, although he reportedly "aced" the quantum theory portion of the Starfleet Academy entrance exam. (VOY: "The Cloud", "Imperfection") During his academy years, he became close friends with Lyndsay Ballard, who lived across the hall in the student dorm. He even changed his class schedule so he would be in the same classes as Ballard. She taught him to ice skate, despite his dislike for cold weather. He never mentioned to her that he had a crush on her, not until he met her again in 2376. (VOY: "Ashes to Ashes") Kim was editor of the school newspaper his senior year. As editor, he monitored subspace transmissions, where he got reports from some of the first activity by the Maquis against the Cardassians after the signing of the Treaty of 2370. Without advising his professor, Kim wrote an editorial on the potentially controversial topic and the cadets became polarized on the issue. They debated the pros and cons of the subject and through his article, gained an insight into the entire history of the Maquis political rebellion. (VOY: "Investigations") He was also a talented Parrises squares player, and was Academy champion three times. (VOY: "Tsunkatse") Harry graduated from the Academy as valedictorian of his class, having earned Interstellar Honors, on stardate 47918. He requested duty aboard the USS Voyager on stardate 47923 and was given his first field assignment as a bridge officer aboard Voyager early the following year.

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