<human>: I have a little bit of an odd situation where I have feelings for a girl, but it's extremely inappropriate to tell her that at this point because my brother and her are friends and her dad is my boss, among other things.

Shortly, given how her life is progressing, I'm going to have to tell her I have feelings for her or I won't have a chance at all. I can't tell if she has any feelings for me, I think there's something there because I can tell she gets jealous when other girls like me, but she's too chummy with me to the point I'm fairly sure I'm more her brother than someone she's interested in. She goes out of her way to contact me at least once or twice daily, and I never initiate contact, but that doesn't mean much I don't think.

My optimistic side tells me that the only reason she doesn't seem romantically interested in me is because she thinks I'd never like her and the situation is almost impossible from her perspective (for details beyond the scope of this post that would possibly personally identify me), to the point it wouldn't be a possibility. So, if I just tell her calmly that I have feelings for her and she can take that how she wants, there's a chance something good could happen.

My pessimistic side (read: rational) says that if I tell her, it'll only cause trouble because she definitely sees me as a brother figure. Also, I'd possibly deeply impact my relationship with her brother if he found out and took it disrespectfully.

I look through the relationships sub-reddit, and see tons of people struggling with the same basic pattern of issue (falling for a friend, wanting to tell them), and I was curious if anyone has actually seen something like this work/fail, and the story behind it. I see a lot of people giving generic advice on it, but I've never seen someone refer to their experience with it, despite how widespread the issue is.

Can you give me the gist of the text in a nutshell?
<bot>: Have you/someone you known ever tried to do the friend -> SO thing? If so, what happened and how did it work out?