Okay, ask nicely for Dylan to leave you alone. And if he continues to stalk you after you asked him and after you've gotten teachers/parents/whoever to tell him to stop, WARN him that you're going to put a restraining order on him....if he still continues, just put a restraining order on him. But if he's smart, he'll stop when you ask him.
As for the other boy, get a group of friends and all ya'll go hang out. Get a girl friend/guy friend to go up with you to talk to him. Before you know it, ya'll will have a conversation going. And from there, it gets so much more comfortable.
-->Getting someone to ask how he feels about you is a very bad idea. Because if he doesn't like you now, and someone tells you that then you're not gonna put that effort into talking to him. But once he gets to know you, and your personality...who knows how things could work out. {Yes, that's from a past experience.}
STORY: A guy asked one of my girl friends if I liked him, I said no because we didn't ever hang out and I had no idea who he TRUELY was inside. So he just stopped talking to me, so of course I was completely confused. But making a long story short, we started talking and hanging out..and we started dating. Now this boy has been my boyfriend for 10 months!. Like I said, you never know how things can work out...especially if you don't give it a try.