Chihayafuru 1 and 2. This is my go-to motivational anime. If I feel sad or I'm stuck in a rut I watch this anime and it seems to pull me out of the gutter. It has depth, romance, hard work, sports/teamwork, friendship, and plentiful meanings (that are explained just in case you don't understand).
Taichi (Chihayafuru)--He was a jerk when he was a kid, but I think people should cut him some slack. He suppresses his feelings for Chihaya because he knows she loves Arata. And he even joins her club and helps her realize her dream. He's not even that good at Karuta, but he keeps trying for her sake. I can't help but feel sympathy for him and contempt for Arata.