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I think it’s great you’re so sensitive to your older DS’s feelings, and understand why your DH would want to keep your younger DS in pull-ups too, but I wouldn’t. Both my brother and I wet the bed on and off until we were maybe 8. I hope for your son’s sake that he outgrows it sooner, but if not, that’s a long time to keep YDS in pull ups if they aren’t necessary.

I feel for your DS. I remember the embarrassment. My parents never made me feel bad about it, but I knew I wet the bed much longer than other kids. I was a super deep sleeper too.

Maybe just don't make a big deal about the younger one wearing underwear? Or if the older one asks, say that you're all out of small pull-ups but yay, there are still big ones!

DD was night trained probably a year, or more, before her big brother who's 2.5 years older. It's never really been a problem, even though they're very competitive about everything else. It's a bit different because we did let him ditch diapers once he was dry most nights, so no one's in pull-ups at this point... his accidents are usually very small so we can handle it.

I wouldn't do pull ups for the younger either.

Another possible option: maybe see if he'd prefer to use cloth trainers (like https://www.nickisdiapers.com/kangacare-rumparooz-lil-learnerz-training-pants-2-packs.html#tab-2 )? Since they are more like underwear, maybe he'd feel less self-conscious?

Do you think it would help DS1 to talk about things that he is particularly "skilled" at, or did earlier than his brother? (he learned to ride a bike really early, or read, etc...)

You mentioned his awareness that friends no longer sleep in pull ups, and explaining that it will happen when he's ready.... but perhaps a concrete example of something that he excels at or did early compared to DS2 would give him some more tangible understanding and make him feel proud of himself, so that DS2 stopping to wear pull ups would bother him less?

@erinbaderin: I tried my old cloth diapers and both girls had pee all over their beds halfway through the night--they couldn't hold the volume of pee and I had doubled up on pads.