My gyn told me to use an old tampon applicator to insert it. Since I use tampons with paper applicators, that isn't a good approach for me, so instead I use a plastic applicator that came with a yeast infection treatment. It is made just like a tampon applicator. Just squeeze the NuvaRing in half and twist it a few times to make it narrow enough to push up into the applicator. I put a little lubricant on the ring to help get it in the applicator, and also put a little lubricant on the outside of the applicator to make it easier going in. Then you just insert it like a tampon. Works really well for me.
That all said, I have been on NuvaRing for five months now, and am having LOTS of side effects--headaches, depression/low energy, low sex drive, vaginal itching and soreness, intermittant weird feeling that I need to urinate when I don't, mild weight gain, and significant hair loss. I could put up with the other side effects, but the hair loss is the straw that broke the camel's back. I am planning to discontinue NuvaRing once I finish this month's cycle. From what I see on this and other forums, these side effects are typical for hormonal birth control.