theres this guy that works were i keep my horse,and he doesnt talk AT ALL,unless you say something to him first.

i wanna become good friends with him and get him to talk more.
what are ways i could maybe let him get comfortable around me and talk more?

Ask him to go horseback riding!
Or tell him a joke/make him laugh.

my trainer asked him to ride in the arena with me,and he did.
and then i saw him watching me a couple of times..
and i was thinking about saying good ride but i didnt want him to look at me like this .
haha.

well, hes a lot like me, then. because im really shy around people i dont know and wont say anything unless someone talks to me first (if i dont know them).

give it time. be patient. but you can try holding small talk.

well like today i was undoing my horses bridle and its basically his job and i undid one and then i felt like he was wanting me to let him do it so i was like uh i dont know how to do the rest so..and then i just kinda stopped talking and he didnt even look or say anything to me..and i was just kinda sitting there.. and then i went to go stand and watch this guy ride another horse and he came and stood beside me..