Need some advice on appropriateness

[Jayce]

Ok so the woman I've been long distance flirting with is coming to my city in a month and a bit, she has brought plane tickets and I've helped her plan the trip. Except she's taking her brother with her. This sounds normal because she isn't coming to just exclusively see me, she's coming because there's a concert event going on, but I asked her if she would stay an extra day and she said she will stay for the weekend. I like her brother, we get along well. But I can't help think this can be bad timing if I asked her out when I see her because what are we going to do, just leave her younger brother (who is still in high school, though he's a senior) in a city he dosen't know for an hour or two? I'm not going to wait for her to ask me out because it's likely that she never will, she's shy and I don't think she's ever dated before either (I've never asked but from what we know about each other it seems like it)

I don't know if it's just my jerkbrain talking but sometimes I feel like maybe she's not as romantically interest in me as I am in her? We've never exclusively skyped, well we skype from home, and I know her brother so it's not abnormal for him to join us, since he's in the house, and plus I haven't asked her out so all of this is supposedly platonic. I like her brother, but I can't get alone skyping time with her and this kind of feels frustrating to me. Yes I know I'm being a bit selfish because we literally type to each other on Facebook for hours, and we exclusively talk every week, and we've sent each other custom birthday cards we made for each other (through slow mail), so it's not like we don't spend alone time together, just not on skype. Plus she likes having her brother around at Skype because she's very shy and she tells her brother to help introduce conversation topics a lot.

Besides all of this everything is going amazing, I feel very compatible with her, she tells me she thinks I'm amazing, we share a lot in common, she tells me that I get her, she pays attention to me, and makes me feel important, she tells me she is comfortable with me and that she trusts me. I don't know if this is a lot but over the span of just knowing each other for about two months we have between us over 2000 messages on Facebook.  She is very reciprocative, she replies to me in detail, sometimes she initiates conversation topics (though she tells me it's hard for her because she often dosen't know what she should talk about, and of course she has a hard time cause she's shy).

I know I've repeated the word shy a lot, but it is definitely a big part of her. I'm fine with that, I do what I can to help her feel comfortable and I'm happy to cater to her shyness.

I don't want to wait another couple of months to define this relationship, I really do want to know if she wants to at least go on a date or not? I'm desperate to know, and I'm not going to ask her out online. Should I really wait another couple of months so I can grab a plane ticket, visit her and ask her out because this timing might not be right?


Edit: I guess I'm feeling a little bit insecure because for the past month I've been the one initiating all our online Facebook conversations, even though she reciprocates every time and she messages me back in detail as well. It's not the biggest deal because I usually just send the first message, and then she replies, and then I reply back, she replies and so on. So it's not that I'm doing a significant more amount so its not a big deal I guess. I'm not bombarding her with messages either, sometimes we have a few days where each of us are off doing our own thing, so within that time there was always a chance for her to message me first, but I always end up re initiating. I guess I want to feel desired as well. I also want that feeling when she messages me first.

I also have a long history of where I feeling amazing about someone and they just don't reciprocate at all, so this makes me feel insecure as well.

And it dosen't help that I was going to Skype with her yesterday after I went back home (cause I was already dressed up so it was a good opportunity) and so we rescheduled for today and well I was out today when she was available and then we I got back home, she was out. So I guess my plan of dressing up beautifully for her on Skype didn't work out (we usually are in our pyjamas when we skype).

[Enail]

To be honest, I think this might be a situation where it would be better to ask her out online than in person. Even aside from the difficulty and potential rude/awkwardness of trying to get her alone when she's with her brother and probably at least somewhat responsible for her.

Asking her out while she's here, or even while you're there, seems like it would be putting a lot of pressure when trips to visit each other are so rare and expensive, it seems like it would raise the stakes of the question a lot. And if she hasn't been seeing your relationship that way, it could feel like you're taking a moment when things are probably a little stressful and off-kilter (because in-person is not how you do most of your interacting) to suddenly try and change the terms.

In this case, bringing it up at a time when both of you are comfortable and able to easily step away to think about things if need be might be better.