What did end up happening with this situation? I see the thread was started over a year ago and I'm curious how it turned out.
I started busking when I was about 19 and didn't know what to do when I ran into people similar to the one you describe. They are not offensive enough to freak out at and be rude to, but they are strange enough that you regret having been as nice as you were. And then they realize they are skating on thin ice and apologize if you got the wrong idea and you feel like a chump, but then they keep pushing their luck. Sometimes they are just extremely socially awkward. More often than not though, they are more messed up than you would have thought and sometimes are even dangerous. Do not let it get to a point that you do not feel safe or comfortable!
I have learned:
1) Trust your what your gut is telling you whether or not you feel you have evidence to back it up.
2) Make sure that other people in your life know who this person is and don't give out any more personal information. Think out ahead of time what you'll say if you are asked for more information than you wish to give.
3) You can be pleasantly assertive. Something like when he says "I'll bet you you're the type of girl that..." etc you can just say, "I'm sorry, I don't give out personal details to people who are not close to me." When he ventures into any sexual harassment at work territory, say matter-of-factly that you don't expect to deal with any of that and should it be an issue, you are well equipped to take care of it. There should be a very clear message to him that those "testing the waters" topics are completely off limits. On the phone, you can arrange to be very busy and answer more shortly. Also make a point of explaining that he should not call you. If he protests that he didn't mean for you to get weirded out, you can pleasantly say, "I'm not, but I am very busy at work". Do not have time to chat after you get off the bus. Bring a book to read on the bus. Do the opposite of the things that make people feel welcome and listened to, and remain neutral and businesslike about it. People like that do not understand or accept f*** off even if you were to say it. Do not get drawn into a discussion of why you have backed off. Think ahead what you will say if asked.