Digi has a crush on Pinkie Pie. Only problem is that she is dating Pokey Pierce. Due to him always holding back during conversation he is fairly reserved which is why he had never.tried asking her out. He would be his true self and he didn't want to pretend in front of her. Now she has been dating Poke since Nightmare Night. It just left his a little heartbroken, jealous, and a bit depressed.