Re: 5 yr old in diapers?
I posted this reply to a similar question. It's lengthy but could be helpful.
I just recently "potty-trained" my 4.5 yr old son. He is my third child so I had opinions about this topic when "training" began. First of all, when my first two children were "of age" (2.5-3yr) I chose to take a cheerful and relaxed attitude; I told them both "Here are your new underwear (which we bought together and they got to choose) and when you're ready, you know where they are". I knew that there were a few things that needed to happen before they were "ready" and I couldn't expect more out of them than they were able to deliver: 1) They needed to know that they needed to go; 2) They needed to have some control over themselves (being able to hold it long enough to get to the potty); 3) They needed to be able to put on their own underwear and take down their own pants easily enough without help and to be able to use the potty (is there a step-stool, etc?). 4) They needed to "want to" go in the potty. For a short while, my daughter would want to "go" in her diaper in the closet. She'd even ask "Mommy, could I go potty in the closet?" and I would say "Sure, honey". I knew she was just getting to know herself - learning that her body did something like going potty amazed her - and she wanted privacy. One day, her frustrated father, yelled at her "No! Go in the potty - that's what it's for!" Of course, she cried and it delayed any progress already made. After I spoke with him to be kind, he didn't do it again and Sadie (daughter) regained her confidence. Same thing happened with my second child (Blake), but it wasn't until he was 3 yrs old. And he needed help wiping #2 until he was about 5, which I was happy to do because at least he was learning and there was less mess.
With Jack (our 4.5 yr old) it went a bit differently - He had the first 3 steps down but he didn't "want" to be potty trained. Some said it was because he liked the attention (he liked being a baby, being taken care of, etc). So I thought "Ok, he "needs" more attention than the first two - I am his parent - why would I deny him something he needs?". I didn't "baby" him, I just changed his diaper and would very kindly (and very occasionally) talked about "When you wear big-boy underwear, you'll be able to ____ (fill in the blank with any reward - including Disneyland)" He still didn't care - not even about Disneyland!! But one day, I was painting rooms in a house while Jack and Blake watched dvd's and we were stuck with no diapers. I told him "Jack, honey, I'm sorry but Mommy doesn't have any diapers, I need you to just go in the potty today - I have M&Ms and I'll give you one each time you go, ok?" And that's how it began. A couple weeks later (and I made sure to not buy any more diapers because he had now proved to me he could do it - with gentle remiders), he was potty-trained. I had watched him closely, and every time his hand went to his pants to "hold" himself I just pointed it out saying "Jack, see how you're holding your penis? That means you have to "go" - get up and go potty now (And if he was watching a movie, I paused it so he didn't feel like he was going to miss anything, and the same went with any activity he was involved with - just pause it). And I never missed a reward. Obviously the reward has to be something he doesn't get all the time anyway or else it loses its' value.
My first thought is to protect the child's self-esteem. I did not want the slightest belittlement (sp?) to take place - my thought was that this would hinder the whole process and create issues down the road. So when our regular babysitter (my mother-in-law) told my son "I won't change your diapers anymore - it's yucky - you take care of it yourself" I was upset. This left Jack feeling that his "caretaker" wasn't willing to take care of him - that it was conditional. Fortunately, Grandpa said he would do it, believing that it wouldn't last forever (and it didn't) Guess who Jack has a better relationship with? Grandpa, of course.