I'd start solving this problem with an earlier bedtime. Like, 7. I know it sucks but if you really want to do something different, that's the place to start.

Can he go to bed while the older one is still dawdling at the table? Maybe he'd be winding down by the time the older one is ready for bed. He might be overtired. It's worth a shot.

No advice, but if it makes you feel better my 21 month old skips her nap all the time and could care less. She still takes an hour to go to bed.

For what it's worth on the cooking thing, I cook a couple of large meals over the weekend, and then just reheat for dinner during the week. Used to be necessary because I didn't get home early enough to cook during the week. Now I prefer it since I can relax a bit with the kids before dinner and/or have a few extra minutes of down time after dinner.

Why can't the nanny reheat food you made the night before for dinner? That would allow him some transition time to wind down after dinner and before bed. May seem counterintuitive, he may also be overtired if the bedtime is too late and having an even harder time winding down.

8:30 is a fairly late bedtime, in my opinion. If he doesn't take a nap, do you push it earlier? Especially with the time change right now, you may need to move it up for a while. I think 7-7:30 is more appropriate if possible. Can you cook ahead of time and just heat up dinners that you premade?

I'd try doing stroller naps if you need to. It's okay to do if you really need to and will at least get him some needed sleep. If he does nap, do you have an easier or harder time with bedtime? Some people find that kids go to bed easier when they aren't overtired (in my experience, my kids both fight sleep unless they are really tired, so it's sort of the opposite for us, but most people seem to feel the other way).

I think it's too early to drop that nap. My kid started dropping his nap a little before turning 2.5, and it was truly too early. I just couldn't get him to nap anymore most of the time, and like you, transitioning to a toddler bed made it impossible to keep him in bed long enough to go to sleep. We tried things like me laying in the room with him or singing to him, etc., and it still only worked a few times a week. I ended up driving him all over the place to get him to fall asleep, and that worked about 80% of the time but sometimes not at all. It was very frustrating, and he was overtired a lot. However, we both needed the break, so I'm glad that I did get him to sleep with driving naps sometimes (stroller naps never worked for him for some reason). We got to the point where he was napping if I went for a drive about 80% of the time, and then it reduced to about 50% and then 25% by the time he was about 3.5, so we dropped the nap altogether.

I wouldn't move his bedtime past 8:30. How much play time outside does he get between his nap and bedtime? I've found it makes a difference for my child when he plays outdoors.

I sleep trained my infant and he still turned into a toddler who doesn't go to sleep.
My self or my husband will sit in a chair in his room until he falls asleep. It can take up to an hour for him to fall asleep and I'll read my phone under a blanket to pass the time. Sometimes he's okay with one of us doing chores within earshot for a while.
It is what it is. He's 3 now and we no longer fight it.

OP here again: okay, let's explore this transition time concept a bit more. We generally eat dinner around 7:30, 7 on a good night, but earlier than that isn't possible. (Said child is allergic to all the things and I have to cook everything from scratch once I get home from work at 5:45ish. Nanny doesn't cook, nor do I want her to given the allergies.) When I get home, the kids are already at home with the nanny, having played outside on the playground at school for about two hours most days, expending lots of energy as I understand it.

They're generally playing around the house as I cook dinner; my husband gets home and then we eat a leisurely dinner (omg, so leisurely due to the snail's pace at which my eldest eats). By the time we finish with dinner its around 8 and up to bed to get my eldest to sleep so he can be functional for school in the morning. It takes at least half an hour to do the bedtime routine, and hopefully lights out at 8:30. The older is pretty good at going to bed and ignoring his brother except when the little one is climbing on him. The little guy then spends the next hour or so climbing all over everything before he wears himself out.

Given all that, I guess I feel like they have plenty of wind down time before/during dinner, and the little guy generally doesn't eat much at dinner anyway, so I don't imagine there are any digestive issues going on, but maybe I'm wrong.

But I'm willing to experiment and let the little guy stay up later in the hopes that bedtime is less frustrating for everyone, but I'm not sure how well that'll go over with his big brother. He can deal though.

Anything else I could try? Am I missing something obvious?

Anonymous wrote:OP here:

Our bedtime routine generally starts right after we finish dinner. Most of the time we'll head straight upstairs after clearing the table. About every other day both boys will take a bath (older brother is almost 5), if not, or after that its pjs and brushing teeth. Once they're ready for bed, we'll read a story or two, and if I'm doing bedtime, i'll nurse him for a few minutes, but that's not a crucial piece of the equation.

Some nights he'll get wound up while we're reading a story, but it usually after the lights are off and everyone's in bed. One of us will usually stick around in the room till both are asleep, otherwise the little one stands at the door screaming. Rocking, singing, patting, all used to work to help settle him down, but none seem to have an effect even more. He's not super verbal, so generally his antics are mostly climbing out of bed and all over everything else (his brother, me, the headboard of his bed, the rocking chair, reaching for the doorknob). We've tried the wordlessly putting him back in bed, but I lose my patience around #20 and it seems to wind him up even more. He generally happy this entire time, unless you leave the room while he's awake.

He has no lovey, or blanket, or anything that he's even mildly attached to.

Ugh, no transition time?? No unwind time? No time to even digest dinner - heartburn, acid reflux! And his blood sugar is elevated now that he's been fed so of course he energized and ready to move around post -dinner. NOt go to bed!

Seriously, I would have a small activity after dinner to burn off the post-dinner refueling. Bring flashlights and go for a small walk, do an exercise DVD, allow some play time with his toys, whatever you think.

Agree with previous poster. Dinner and straight to bed sucks. Take him outside after dinner. Bundle him up, kids do not care. Let him look at the stars and moon on a walk around the block. Then to the bedroom to read a book. Tuck them both in and then leave. Do not wait until he falls asleep. I do not know why parents do this. What is he getting out of that? Let him scream all he wants. If he leaves the bed, put him back in and say no firmly. Big brother will have some stressful nights until little brother gets his act together.

What's the pre-dinner routine?

I found that when our twins were in this phase, at least on weekends, I would head to the playground for 1-1.5 hours before dinner and run them around as much as possible. The problem is that toddler/preschoolers build up a lot of energy in the afternoons especially when they still nap. They need to discharge a lot of that energy or it will keep them from falling asleep.

Another alternative is to move dinner 30 minutes earlier, then do something energetic for 30 minutes after bedtime, then wind down. On days like now when it gets dark soon, I will sometimes pull the cars out to the driveway, close the garage door (we have a 2 car garage) and have them ride trikes/bikes in the garage for 30-40 minutes. That's often good for discharging some of that pent-up energy.

Even at 5, we still have a baby gate on their bedroom door. If they are too wound up, we close the gate, turn out the lights in the room and hallway, so that only the nightlight in the hallway is on and then go downstairs. The rule is that they don't have to sleep, but they have to be quiet. And if one wants to go to sleep, the other has to let them. If the gate is closed, I will open the gate after they fall asleep but before I go to bed just in case they need to use the bathroom in the night.

OP here:

Our bedtime routine generally starts right after we finish dinner. Most of the time we'll head straight upstairs after clearing the table. About every other day both boys will take a bath (older brother is almost 5), if not, or after that its pjs and brushing teeth. Once they're ready for bed, we'll read a story or two, and if I'm doing bedtime, i'll nurse him for a few minutes, but that's not a crucial piece of the equation.

Some nights he'll get wound up while we're reading a story, but it usually after the lights are off and everyone's in bed. One of us will usually stick around in the room till both are asleep, otherwise the little one stands at the door screaming. Rocking, singing, patting, all used to work to help settle him down, but none seem to have an effect even more. He's not super verbal, so generally his antics are mostly climbing out of bed and all over everything else (his brother, me, the headboard of his bed, the rocking chair, reaching for the doorknob). We've tried the wordlessly putting him back in bed, but I lose my patience around #20 and it seems to wind him up even more. He generally happy this entire time, unless you leave the room while he's awake.

He has no lovey, or blanket, or anything that he's even mildly attached to.

What is your transition to bedtime like? Is he playing nicely and then all the sudden you abruptly end his playtime and make him get ready for bed? Or do you read a bunch of books to set the quiet mood before hand?

How much older is his brother and what sort of a distraction is that?

Can you describe how he fights bedtime? Getting out of bed constantly? Talking non stop with brother? Wanting to get out and play some more?

OMG, this is getting out of control. Not quite 2 year old is in a toddler bed because he can climb out of a crib. He's never been great at falling asleep, but we've had periods of progress. Since the bed transition 6-8 weeks ago, he's really, really ramped up on the fighting sleep, particularly with my husband and I. The nanny has had better luck and he'll fall asleep on his own for her if no one else is around, but on days that I telework (1-2 times per week) he screams his head off for an hour when he's clearly over-tired. Bedtime is equally tortuous for both parties. He's clearly tired, but gets all ramped up at bedtime despite a consistent routine and just will not settle down and fall asleep. It takes 60-90 minutes to get him to fall asleep every night. He shares a room with his older brother, so I can't just let him cry at night, though there is a fair amount of that going on regardless.

For a while I thought maybe he was ready to be done with his nap even though its super early for that, but given that he does consistently take a nap for the nanny, I'm reconsidering that line of thinking. We never formally sleep trained, and i feel like we missed that boat when we had to ditch the crib. What to do now? Any suggestions for what to try next?