Anyone gotten past the repeated rejection with Matthew?

Matthew's caring stays intact even after two rejections per the setup, which keeps the friendship warmth from curdling into something purely painful. What I can't figure out is whether there's an approach that actually moves things forward, since he hasn't realized his own feelings yet according to the description. Does the story ever shift on its own if you keep the friendship going, or does confessing a third time just loop back around to another no like the opener implies?