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Is he still napping?

@SeptMomma12: The sleep lady shuffle that @hilsy85: mentioned really does work! This is a good writeup of a similar approach:

http://www.parenting.com/article/how-to-get-your-kid-to-sleep-in-her-own-bed

I like the idea of a Sleep Fairy!! That might work with my kids.

We did the lock on the door for my son and that worked. He pretty quickly figured out how to self-soothe and slept through the night on his own again. Gotta do something similar with my daughter now!

I know you said you don't want to bring him to your bed, but I'm a big believer in whatever works at the moment to get everyone sleep. My LO is the same way in her own bed, we finally gave up and let her sleep with us, and we are all much happier and rested. She sleeps all night long in our bed and we all get sleep. I figure she will want to sleep on her own eventually!

@SeptMomma12: We didn't do checks, but he responded very quickly to the lock!

http://www.hellobee.com/2012/07/17/how-to-avoid-sleeping-next-to-your-child-until-they-fall-asleep/

In your case, it seems like he has some anxiety... so I would sleep on the floor with him for a few days, like that parenting.com article suggested. Then I'd do the transition to the chair, to the doorway, etc.!

Do you have books on toddlers sleeping through the night? If not, it might be worthwhile to write a quick story with him in it! About how he woke up in the middle of the night, but then went back to sleep because he was a big boy and knew that his parents loved him very much, etc.

@SeptMomma12: I am having the exact same struggle with my daughter who is 2yrs 8m. Her sleep has been getting worse and worse, but it's been particularly bad since about a week or two before her baby sister was born in late May. Fortunately my daughter is not waking up every night (and when she does, I just have to stay with her for a few minutes until she falls back to sleep), but nothing I am trying is getting her to bed at a reasonable time. Last night her bedtime routine started at 7:30 and she finally fell asleep at 11:30. I am going back to work in 3 weeks and this NEEDS to improve!!!!! She is whiny and not herself.

Some of our problem might have been due to her sleeping in since I have been on maternity leave. I try to get her up at the same time, but sometimes it is hard when she's gone to bed late the night before and I am tired and want to sleep in too! I've really been forcing myself to get up though lately. We also went on vacation to the west coast for 10 days (we live on the East), so she also had some jet lag for awhile... that may be still in play... I know I am going to bed later as well.

She also naps for 2.5 hrs at school (they all do), though she doesn't consistently nap at home. When she skips a nap at home, she sometimes goes to bed a little earlier, but sometimes she is overtired and has a more difficult time.

I think she is just naturally a night owl and a high energy kid, so that is part of it. Then I'm sure the change with the baby had a lot to do with it. She loves her sister and never acts jealous, but she acts clingy to me sometimes and won't allow anyone except for me to do things for (e.g., buckle her into her carseat, change her diaper, dress her). I swear, she says, "I want Mommy to do it" 50x per day.

On occasion, I've found watching a show with her on the ipad, in her bed, works to calm her down. But then it doesn't work the next day! It also sometimes works for me to respond to requests for me to lay down with her by saying, "Sure, I am going to go put your sister to bed and then I'll come back and lay with you, as long as I see your eyes are closed." Some days she will fall asleep before I get back. A few times it has worked for me to lay down on the floor next to her and hold her hand until she falls asleep. The trouble I'm finding is that what works one day, doesn't work the next. I've tried gating her in the room and ignoring her requests until she fell asleep totally on her own (she did so happily, for the most part, but not until midnight); I've tried locking her in - she cried it out and fell asleep, but it took like 45 min and I hated every minute of it (but then it didn't work the next day - I gave up after like an hour).

I just bought the Sleep Fairy book and one other one (The Girl Who Got Out of Bed). Books and tv programs do sometimes work for her on other subjects, so I think that's worth a try. I'm going now to look for a tv episode about sleep...

I've tried offering rewards for sleep and it worked once, but didn't work the other times I tried. I haven't tried a chart though, so I'm off to make one now.

I'm going to try to squeeze in some vigorous play before dinner to see if I can do a better job of wearing her out.

Sorry I am not much help, but I TOTALLY feel your pain!!!!

I'm browsing printable reward charts and what I think I'm going to do is find or make one that has pictures of each activity in her bedtime routine, including going to sleep and staying in bed. We have not been 100% strict about her routine (because I'm been experimenting to see if ipad, bath, etc. helps her settle or makes things worse), so I think a chart would help me. I'll just have to pick a routine and go with it for awhile.

My LO will be 2.5 in Sept. We converted the crib to a bed two months ago. It was great for about two weeks and then he too got progressively worse about getting out over 20 times at bedtime & again middle of the night & again at 5am.

It got soooo bad that we just converted it back to a crib this weekend. He was very upset the first night and it was hard for me to let him cry it out because we also never needed any sleep training and I didn't want him to just feel abandoned and give up hope on us coming to help him after 2 years of happy bedtime! Soooo I laid with him for about 30 minutes and then said "I have to go to sleep in my room now (cue fuss). If you lay your head down and rest I will come and check on you in a little while). And then he fell asleep and I never needed to come back and bedtime is peaceful again. Going back to a crib is probably not an option for you at this point but maybe use the gate and tellhim you will come back and check on him if he lays quietly for a few minutes?

All of this said, since I'm in nearly the same boat I am no expert and will be reading all the advice closely.