So get your cameras ready! These tips will work for simple point and shooters as well as DSLRs and film.
#1 Use the shade, or otherwise, put the sun behind your subject.
This one might be tricky if you are chasing little ones around the playground, but as a general rule of thumb, outdoor portraits come out nicest in the shade. This eliminates squinting as well as harsh sunlight shadows on faces. Turn on the camera's flash.
If no shade is available, put the sun behind your subject. Their hair will be lit nicely and and again no squinting or shadows. NOTE, this may mean that the sun is shining directly into your camera... to avoid flare (bright sun spots on your pictures), use the lens hood or shade your lens (with your hand, an umbrella or whatever is handy).
If the sun is directly overhead or there is no possible way to avoid it because you want to shoot a certain background, there is one trick I use to avoid squinting. Ask your subject to stare at the ground until you are ready to take the picture. Tell them you will count to three and when you say "go", to look up and smile. You can catch a nice open-eyes picture before they start to squint.
Oh... this contest is going to be fun! Please spread the word... I have so many tips and tricks to share. Also, I don't have that many followers so anyone entering has a pretty good chance of winning! :)
Here are some samples for you. Notice how much better the one in the shade looks compared to the one in the sun:
Have fun!!! See u tomorrow :-)