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Thread Starter 
I know that there are threads on this, but these things have such a steep learning curve, I thought I'd share what I learned in the hopes that another newbie has a less steep learning curve. Please feel free to add your own experiences/suggestions. I have a Diva cup, and am really starting to enjoy the benefits.

Try putting it in in the shower. Your hands are clean, the cup is clean, and everything is wet, so it helps things slide better. You can also do a little tidy up after you situate it, which really seems to help keep undies clean. And, if one of my girls walks in, I don't have to explain what I am doing....

And here is the big one I wish I'd known - it may help to pinch/fold it again when removing. I don't think I saw this anywhere in the instructions, and taking the thing out was really, really painful for me. Not quite as bad as a baby crowning, but still just too much stretching. That was almost a deal-breaker for me.....