The title of this post describes our efforts at toilet training. With Eric, we plopped him on the toilet for months, then suddenly, magically he was toilet trained. (This also happened to someone in Zoe's class.) With Zoe, we have not yet hit the elusive payoff. I put her on the potty every day. Sometimes she goes there when she needs to, sometimes she doesn't and wets her pants instead. I put her in underwear every day. Sometimes they stay dry, sometimes they don't.
I remember a friend of my mother-in-law's telling me that her daughter was wearing pull-ups until age 4 or 5. Then a kindergarten friend saw the pull-ups in her closet and said, "Ew, what are those?" Hopefully we won't get to that point.