Coming Out of the Shell

I've been noticing something interesting in myself lately. Most of my life, I've been really quiet and kind of shy. Later in high school I came out of the shyness a lot, but was still pretty quiet. In college, it would seem I was neither. But lately, I've been noticing my behavior around people I really like (whether admiration or crush or whatever) and it reminds me of when I was younger. There's a woman at my church that I've really started to look up and want to ask her to have lunch and maybe even to be my mentor, but I get so nervous about it. Like when I see her online, I'll want to chat, but then I think "What if she thinks I'm bothering her," or "She's probably really busy and won't want to talk." And that fear will actually paralyze me a little and stop me from saying anything- like now. But I really like her and look up to her. The way I see her follows a trend I've noticed since high school and identified since early to mid college. I'm drawn to women I see as strong or authoritative or women in power. I think it has to do with mother issues. I never had the kind of relationship with my mother that I wanted. She was a great mother physically and even spiritually, but I spent a lot of time as a kid emotionally mothering her. I never really felt like I had a strong mom I could just lean on and find comfort from. So when I see these women of power, I'm drawn to them and want to absorb their motherly wisdom and affection (that sounds really weird). I've seen it so far in my relationships with my high school choir director, both of my staff workers, my bosses at work, my old pastor's wife, and now this woman at church. It's not even always conscious. I just start noticing that I want to be around them more and want them to approve of me.
It's so weird. I don't want to become that shy little girl again. One on one conversation is where I "shine" the most. I'm pretty personable in that way. But in group settings with people I don't know very well, I'm pretty quiet and don't really know how to interact that well.
Interesting how personality traits from before college start to peek back out after college. Guess it goes to show certain things may go dormant, but real change isn't very easily accomplished.
So now, I'm trying to figure out what to do. I really look up to this woman and would really like to get to know her better. It would just take some risk on my part. Guess I don't want to risk getting rejected or getting a response that feels like rejection. It would make me sad and I would probably feel awkward around her. Maybe that's part of what I'm afraid of: damaging the relationship we have now.
Then there's the boy. The way I've felt about him has been so off and on, it's just been confusing. One year I like him, the next not so much, then I do, then I don't and so on. This time, I've pretty much decided I'm just going to ask him to hang out (as friends) so we can just get to know each other better. I wouldn't put it quite like that. We're good enough friends that I think I can ask him to hang out and it not be weird. I just want to see, see if there's anything there. The thought of it, though, is both exciting and scary. And I'm frustrated that I don't have my phone available so I can't really do it yet. So I've made this decision and am now just sitting on all this anticipation until I can do it. ahhh!