OK I know some people might be horrified at this... I’ll just give you the background first. My DS and DD share a room, DD is great at going to sleep by herself but she needs the door closed so it’s nice and dark and quiet. DS is mostly ready to go to sleep after DD and he needs us to help him go to sleep and he must have the door open. So it just doesn’t work. As soon as we try to put DS to bed he wakes DD up. Our solution is that we just let DS fall asleep on the lounge with us and carry him to bed when he’s out to it. They both mostly sleep through the night and if they wake we don’t have too much trouble settling them again. There’s always a bit of random co-sleeping going on with either one (or both) of them at times as well. Neither of them have a set bed time because when they get tired really depends on how much sleep (if any) they’ve had during the day. I say horrified because I know some people will think that letting you child fall asleep on the lounge every night is just stupid. But we’ve tried other things and this is just what is by far the most calm, peaceful, functional way of dealing with different bedtimes, different going to sleep needs and DS + DD sharing a room for us as a family.