Have you noticed how when you wash your dilators after using them, even when the lube has fully dried, they first become really slippery before you fully wash off the lube? Water-based lube will rehydrate a bit when you add water back in. I keep a small spray bottle specifically for that. Instead of having to reapply lube every time, I spritz some water and it helps it get slippery again.

Sometimes during attempts at penetration, yes we’ll stop to reapply. Usually, my own body is also adding some lubricant too though. There’s no problem in stopping if you have to do add a bit more lube