Can you give me advice about this girl?

Question

I'm twenty and my best friend that I met in high school has a sister who is a year older than the two of us. She's training to be a nurse, so she's a great conversationalist and really easy to talk to. Very down to earth, but also fun and lively. She’s both passionate and intelligent. Basically, the kind of qualities I look for in a woman.

Last weekend I went to the New York Auto Show with her and her brother. Because her brother, my friend from high school, dorms at a college farther away, we took a train to meet him. I hadn’t seen her for some months since I only see her when hanging out with her brother. Nevertheless, we connected very well together. This continued at the show. Her brother can be a prude and at one point he walked out in annoyance of a crowded area with custom cars and loud club music, so I walked with her alone. Later my friend insisted on seeing Buicks, so I called him a 70 year old man. His sister laughed and really picked up on this, making fun of him for it too. On the train back I became distant because I was confused about my feelings. It wasn’t awkward though, because she’s such a great conversationalist. When we reached her parent’s house I bailed with a semi-true excuse about my mom’s birthday. I was still confused and thought it would be improper. It may have been the framing, but I feel like I spent the day with my friend’s sister and my friend happened to be there, unlike usually the other way around.

Now I have decided I want to pursue her, but there are some complications. First, I have decided to drop out of college. When she asked me about this she seemed completely non-judgmental, which made me like her more. I have started a business and am not unambitious, but since my business is just starting I don’t have much to show for it. I sometimes think I won’t be good enough to focus on dating until my business is successful. Another thing is, as a nurse in training, she seems to be very busy with her life. I don't plan to ask her out now, but I would like to continue developing a connection with her. That's the third problem - I don't see her unless I'm hanging out with her brother and I can't think of reasons to see her otherwise unless it was a date. I plan to get closer to her with every opportunity I get and in a year she'll graduate, I'll be a full adult and hopefully have a successful business, and then I'll ask her out casually. I'm not terribly worried about her brother and I get along great with their parents. I think she likes me a least a little and we get closer every time we meet. If it weren't for these complications and based on just pure feelings I'd probably ask her out a lot sooner.

I've heard twenties are the time when people want to date most and the worst time to actually do it. I'm caught in the awkward situation of wanting to see a girl, but having no good reason to do so. I'm typically a patient guy, but it is hard to ignore my feelings. If anyone has suggestions on how I can move things along with her, even a little, I would appreciate it.

Answer 1

Best Answer - Chosen by Voters

Wow. You took the time to write all that.. You must really like her! Tell your friend you want to hang out, the three of you, and talk to her more. It's not hard if you use your friend, your only resource, as a stepping stone to see her more. Asky yourself.. Will your friend mind? Shouldn't you wait till AFTER she gradutes? And does SHE even like you?! Not trying to sound rude at all, but females don't like being pressured into falling for someone. Like I said, ask your friend to hang out and say you like hanging around his sister.
TIP. Girls like guys that can make them laugh.

Answer 2

I would say that for now just start as friends and then go out with her when your lives aren't as chaotic. You'd still get to see her and get to know her this way. Hang out with her brother alot too. You may learn more about her that way and maybe see her then too.