As far as the "asking" vs "telling" goes, I wouldn't make a big deal of that. Is that a power struggle you think you can win? Is it worth it?
I will preface this by saying that my dd is very trustworthy and has repeatedly proven to have a great head on her shoulders.
My dd is 13 and in the 8th grade, and she calls me (or her father, depending on who is available) every day with her plans for after school. Generally she tells me what she is doing: "Hey, I'm going to stay in the library and work on a project until 5" or "We're going downtown to get coffee". These are things that she is generally allowed to do. If she's doing something out of the ordinary, she usually frames it as a question; but honestly, I don't think my response would be any different.
She doesn't hang up on me immediately, there is always discussion about who she's working/hanging with, will they get home under their own power or does she need a ride, what's going on in the evening, etc. She's a fairly reasonable gal, and if I say she needs to come straight home for some reason, she's fine with it. Her friends are low key, I know them all very well, they are all good students and good kids, and I trust my dd to not be stupid.
On weekends we usually ask her what her plans are, and tell her what *our* plans are, and if we have any family plans that involve all of us. Often she goes to a friend's house or some friends come to our house, or she and her friends meet somewhere downtown for coffee or dessert and to hang out. Depends on the weather. Sometimes we tell her no, but usually we don't have a problem with it, as long as she gets her chores done and can get in some music practice. I guess my kids has quite a bit of freedom, but she's earned it and has not abused it.
We also live in a smallish town. I know if she were being a punk I would eventually hear about it from neighbors, shop owners, etc. When she broke her helmet strap and had to ride home with the wind in her hair once last year, I got TWO phone calls about it. Her aunt saw her and gave her a lecture and then called me to let me know my kid needed a new helmet, and another kids' mom called me to tell me she saw my kid riding without her helmet and she knows we don't allow it, blah, blah, blah. I figure, if riding a bike without a helmet one time causes that big of a stir, imagine if my kid was downtown smoking or being obnoxious? I'd have to turn my phone off!
The car involvement may freak me out a little. I mean, I wouldn't mind if *my* kid were the driver of other kids, but do I really trust someone else's kid? Obviously this is something I'm going to have to let go of at some point, but dang, that's what would get me the most!