Questions about dudes

Alaina
There's this guy that I know through mutual friends, he is super sweet and kind, we have hung out a couple times in a group, but I like him, I don't know if he likes me, we message sometimes but not a ton. I want to know if he likes me back, he sends winky faces and things that (to me) are flirting, but at the same time, he doesn't ever message me first, I am always the one to message him first... What should I do? Should I keep messaging him? Or just stop? 😕