My son is starting high school next week, and had to go to a daylong retreat for freshmen today at his new school. (I posted on another board a while back about challenging him academically, or sending him to a school that he thought was a good fit. We went with fit.)
On the way to the retreat, he asked, "Mom, who should I be at this school? And don't just say, 'be yourself,' because I don't know who that is, and it won't be helpful."
I wasn't taken aback at all, because I remember feeling the same way at his age, and even years later, so I just listed the traits I saw in him that were attractive to others (quirky humor, empathy, compassion) and told him it would be wise to tone down the ones that could be offputting (know it all, tendency to be very literal, strong negative reaction to sarcasm).
He thanked me very solemnly and it was all I could do not to cry. I want so much for him to be confident and happy at this new school, but I know that there are no guarantees of anything.