Does he like me?

So Drake and I are really close friends. But I'm wandering if we could take it a step farther. He's been over to my house to swim, watch movies, parties, etc. and I've been over to his. He takes me home or to my moms work from school everyday. He is shy and doesn't show much emotion. We have spent a lot of time together with friends and sometimes alone. My family loves him and we are really close, all of our families. Should I text him first? What should I text so he would text back? Keep it mature but not too much, we are in high school. I want to flirt a little but not to much. He isn't dating anyone. Thanks!!!