after seeing their back story, she not only went into their relationship with eyes wide open, she actually gave up a year of school to try and 'entangle' him into her life. Unless there's a twist, my opinion is, he always cared about and appreciated her, like a friend. He felt obligated to go out with her, but he didn't mind because he did care about her. Perhaps he's never been in love, so didn't know what he would be missing and thought it was fine. And now, perhaps he believes she has moved on and in a romantic relationship he no longer has to fill that spot, but still cares about her and her place she made in his family. I find their story just sad and wasteful, but the conniving person is the FMC imo. Even she says she helped take care of his father to be close to her crush.