taking new female friend on trip

[nebulous]

Here is my dilemma, I met my cousin's neighbor 3 weeks ago at my cousin's birthday party. She (the neighbor) stopped over late at night after the party and had a few drinks with me and another cousin. We all talked the night away and sometime during the night we found out that the neighbor had never went up north before. Of course we invited her up and my cousin said we could stay at her house since she lives up there. She is definately cute and I would be interested in getting to know her better but don't want to scare her off since she is skittish when it comes to men.

 

We have talked on the phone only a few times and then only when one of us has something to find out from the other. We did go to an amusement park this past weekend and rode the rides together and had a great time with her brother and another one of my cousins. She is hard to read and I can't tell if she is in to me at all other than friendship. I asked her on the way home from the park if she still wants to go up north and she said yes definately.

 

Another thing is her brother took me aside this weekend and told me that he never likes any of her boyfriends and said that I should hook up with his sister. I don't know if this is his idea or if she said something to him about me.

 

My question is this. We are going up north this weekend and my cousin that lives up there and offered her place hasn't returned my calls since I left a message telling her that we were coming up there. I have a trailer up there so it's no big deal but I need to know how to proceed on the trip and how to handle the whole who pays type thing. If she isn't interested I don't want to scare away a potential friend but I don't want to miss out if she is. She has inquired about a potential new job I may be getting, where is it, what kind of work, that kind of thing and other things like that but never really opens up too much. I think this is cause she was hurt in the past and had a nervous breakdown. Any advice would be appreciated. Thanks.

[Thor]

So, there may be a few ways to interpret the situation you're in now. However, before I do, I wanted to comment on the whole brother thing. Never, in my entire life, have I ever known any of my friends who were brothers to try and hook their sister up with someone. It wasn't always a look hard and mean at anyone who came near their sisters, but it definitely was never about hooking their sisters up. So I'm really not too sure about this girls brother.

 

Anyways, about your upcoming trip. For the first few times, I'd think that you should let her pay for some stuff. If you really want to offer to buy her something then start out small. Say you're at lunch then offer to buy her a piece of pie or ice cream or something like that. From that, try to determine what her demeanor is when you offer. If she starts to play with her hands a bit, look away from you and says no then she probably isn't comfortable with you just yet. But whatever you do, I probably wouldn't make any moves on her while you're up north. This courtship, if it's going to be a courtship, will likely span a few months if you're willing to invest that time. Sounds like she's had a hard time in the past, and in general, women rarely let go of those feelings very easily.