positive fun messages but he texts back really short responses.
Most Helpful Guy
You need to find out topics he likes and his interests to talk about. Try to know what he hates and talk about that, it'll make him to talk. Start by talking something similar between you both. Something you both hate or something both like, this will gain his interest in talking more!
Most Helpful Girl
Ask him about what he likes and talk about his day, his life etc