I'd say to wear a pad the first cycle or 2 esp for overnight. jic! I have super heavy periods at times so I ended up buying some cloth panty liners (rather than full pads) to wear when its super heavy.

I did trim the stem off completely for comfort. If you can feel it, its prob not inserted properly (or the stem is too long). for me, I find that once its inserted and I rotate to make sure its open properly, I bear down trying to expel it while I manually push it in gently. It does take longer to insert than a tampon if you include washing time, but the tradeoff is that I usually only have to empty it 2 or 3 times a day.

I try and time it so I'm not changing it while out and about but I keep a few wipes in my bag in case I do need to.

I my diva cup and will never give it up. Not only is it way more comfy and convenient than tampons/pads, but for what I spent on 2 cycles worth of disposables, I've gotten 5+ years worth of use out of it.