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Practice on your sister , mother or friends as much as you can because it is in a controlled environment and it isnt creepy ie. hey sis (when her hair is up) you look much better with your hair down because it looks better when it dances on your shoulders - this is where you would normally kino by brushing her shoulder to show her where it would look good - you dont need to do this with your sister. Transversly if it is down pull it back into a pony tail and have a look at her face and say - mmmm yep that looks better - just one example.
I have found practicing on co-workers and girls you do business with (ie hair stylist), also make good practice targets.
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Alot of women that age 16-20, have alot of insecurities, even the most confident ones have fragile ego's, myself i have had a few backfires with negging women (18-21). But firehouse i think hit the nail on the head with finding a good calibration on negging.
You may want to expand that age range of yours. As I say girls from the age of 12/13 all the way up to 60 will have a fair amount of insecurities, mostly with their bodies.