delbows, I think I might be a family member... definitely cut from the same cloth as your kids.

To the OP - is it possible to let/encourage your DD to be a little deviant now and then?
What I mean is maybe instead of being focussed on doing everything the correct way, she could deviate. Like drawing on her bedroom wall or drinking out of the milk jug or something like that.
My cousin's DS grew his hair long, dyed it black and slunk around like Harry Potter in middle school. He grew out of that phase, but it definitely helped him shed the uber nerd mantle that had had been weighing him down. He's the same nerd, but now he fits in. I think he's just more confident.
DH had to help one of his college students by making her promise to never, ever study on Friday nights. She went on to wear make up and even a mini skirt, I think. She's still a nerd and she's getting her PhD in biophysics, but she did graduate college feeling like a bad*ss.
I took no risks as a child. Not advisable.