I have a DivaCup, and it works okay. I've been using it since November, though I took a break for 3 months while I was on the ring (I just stopped using it). Peeing always took a little longer than normal while the cup was in. This cycle, I can't pee while the cup is in. It's painful if I try. Everything's fine if I remove the cup though. I'm guessing the cup is compressing my urethra?
Would this be fixed by getting a new cup? I'm definitely not against that. The DivaCup is too long for me. My cervix is very low-lying and I can find it during all parts of my cycle. This means the end of the cup hangs out a bit. Surprisingly, it usually isn't uncomfortable.