My experience of regret is actually the opposite of yours, though I do enjoy your sense of humor. When I was in high school, I gave up just about every opportunity I had to take a risk and have some fun. I was a goody two shoes. Too pure to ever get in trouble, but also too plain to be memorable. Almost everyone forgets my name, but they remember my siblings very easily. Now I am in college with good grades, but a lack of social skills and I am way too serious for my age. I think joking around and having a bit of fun shows plenty of character. Staying quiet and strictly obedient to every rule feels like a lack of personality to me.