Okay, so my 16 year old tells me today that she read her "friend"'s college essay and it was really good. She seemed jealous and told me that she hopes this girl does not get into a good college.

I was upset at my daughter's mean-spiritedness. And, so I asked her why, if something happened, does she not like this girl?

Well, something did happen and I know what it is/was. It happened a year ago. This girl "dumped" my daughter and a bunch of other girls to become friends with these three other girls.

I might have asked my daughter other questions or pointed out that it didn't seem particularly nice that she didn't want this girl to get into a good college. I think I said something like, "what difference does it make to you?"

And, so she just got upset with me for making her "feel" bad.

I have been trying to discuss emotions with her because I've read that kids do better if they come from families that discuss emotions and can understand their own emotions. But obviously, my daughter is not appreciating what I am doing.

And, so I guess, I should first of all respect my daughter's boundaries? Obviously, I'm making her feel bad. And she is not appreciating me poking and prodding. Am I doing something wrong in general? Or did I just start too late with her?

She's very quiet and doesn't have many attachments. She has lots of great traits but I didn't handle her shyness well when she was little. I probably overprotected her instead of encouraged her to get out there and get hurt and stand up again.

I get so fearful that she will go off to college and not be able to form relationships and do something drastic, like overdrink or engage in otherwise risky or unhealthy behaviors.

My anxiety is so strong at times and I realize I have to let her go and live her own life and make her own mistakes. I'm just not sure if I should keep trying in the emotional arena? She just seems so mad at me lately and mad at others at school, etc. - though T said that's a good thing, at least as far as I am concerned, that she has to separate and individuate.

Maybe she's finally feeling her own needs not being met and she's getting pissed off and being more assertive?