After reading all this it seems that you don’t have much experience being around boys or relationships in general and thats not a good or bad thing. First you should realize that he likes you. You can be direct and let him know the truth. Tell him that you do not think what he is doing is appropriate and that you are not interested in going out with him. Saying you want to move to Lakewood is just hinting and some guys (like me) just don’t get those types of hints. Learn to say no when he asks you to do things that make you uncomfortable (like playing non Jewish music). At the end of the day its your decision and don’t stress yourself out about things like this.
The whole dating process is not easy and even when you find someone and you think they might be the one, it might not work out for various reasons. Sit back and understand that G-d has a plan and it will work out.
I’m a guy and I’m going through the process myself, so I understand there can be trying times. I’m coming from a more OOT MO YU type background so my experiences are completely different.
One thing that you wrote disturbs me. You mentioned that it was a good thing you never had a boyfriend (fine). But the reason you gave was because you don’t trust boys, yet you want to be set up with one (red flags). You do realize that if you don’t trust boys, then you are not ready to date one. If you want to have a good marriage then your relationship will have to be built on trust. If there is no trust, then what happens when you have kids? Will you trust your husband to make good decisions on how to raise them? Maybe I’m reading into that too much, but I recently was going out with a wonderful girl who had gone through some very hard situations and had never been in a real relationship before. Right as we were about to be much more serious, she realized that she was not ready to open up so we ended it.
Sorry for the long post.
Tl:dr Be direct with him. Sit back and don’t stress about the dating process, it will all work out. Don’t date until you are truly ready.