Try using a polarising filter at 90 degrees to the sun instead of flash - it's what I used for my shot on 28th July... It'll remove the glare and solve the shadow problems.

Most of the time, Yinks, I have no clue what to do, but as a rule, I avoid using flash like the plague. BUT I have seen the attachable flashes that portrait photographers use and have it in the back of my mind to pursue some day!

i like this image
i think mostly cos of her expression

a polarizing filter will remove glare (dunno about shadows) but will rob you of some stops (there may be those that don't out there tho)

the flashless way to do this is with reflectors... good news is almost anything can be a reflector (i've gone as far as using a leaf from a photo album...try the gold kind, works magic)

with flash, and i assume you have a camera dedicated flash with swivel and bounce, just reduce the power of the flash to as low as will make a difference and bounce it off any where that will complement the shadows.
you could even bounce it off the table (but remember to white balance appropriately)

as yoda would probably say...'perfect!...practice makes'

I'm going to tell her U have plenty of advice here that I have also taken.