I've been reading posts here for a while but never posted myself. I've been struggling to use my Diva cup (tried both sizes) for a couple years. Sometimes I gave up and went back to tampons but I kept going back to the cup because I love the concept. I finally found some tips that really helped it work for me like enlarging the little holes and lying down to put it in. I'm on my period now and it's going very well! But I've also realized that maybe the Diva isn't the best cup for me so I bought two MeLunas from mcsales and am eagerly waiting to get those to try my next cycle. If they don't work, I'm trying a Fleurcup. It took me a while to accept the idea that I may have to try different cups and that the Diva not working wasn't necessarily operator error.
But I just want to thank everyone in this helpful community! What a resource! It's amazing. I'm 44 and I'm just sad I didn't discover cups in my teens or 20s! And you can bet I'm going to turn my daughter, nieces and young friends onto them when they get to that point.