It took almost two years, but finally, finally we have bedtime success! Let me start at the beginning so that those who are where I was don't feel so alone.
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Bedtime has always been a struggle for us. As a result, we developed what some would consider bad habits. I tried several techniques described either in books I read (books that I loved and thought for sure would work for us), found online or were used by friends and family to try to get my son to bed on his own and at a reasonable hour. We have always had a bedtime routine (the typical bath, book, bed type) but my son would not go to bed on his own. Yes, I am sure if I implemented the cry it out method it would have worked eventually, but I just couldn't do it. I was in a situation where my son had to be sleeping before being put in his crib for well over a year. On top of this he was going to bed way too late for a little guy at around 10pm. He wasn't lacking sleep as he would sleep late into the morning and take a lengthy nap in the afternoon but my husband and I never had time to ourselves in the evening. Mom and Dad should really have some Mom and Dad time.
For a year I nursed my son to sleep day and night. After that ended I would get him to sleep by putting him in his swing (yes we used it way too long) or rocking him until he was out and then would ever so carefully place him in his crib. Then I got pregnant and my pregnant belly just couldn't handle the bending over into the crib towards the end! It was hard enough to rock him on my disappearing lap! So we transferred to a toddler bed. Again, I tried to get my son to go to bed on his own, thinking this was a new, exciting way to get him on board. Nope. Now he could not only scream, but get out of bed over and over again.
I think part of the problem was that we were in a one bedroom apartment. My son could see my bed with me not in it and hear the tv in the other room or Mama and Papa talking. He wanted in on the action. If we got the boy to sleep at an earlier hour he would wake at least once prior to us going to bed and we would have to start the process of getting him to sleep over again. This usually meant turning off the tv and lights even though we weren't ready for bed ourselves. My son wasn't able to soothe himself back to sleep. When we put him to bed later in the evening he tended to stay asleep and when I was pregnant, this is what I cared about more than his bedtime. A full night of sleep was my priority. If I was woken in the middle of the night it was rare that I could easily fall back to sleep.
I felt guilty for a long time about our bedtime habits. I was ashamed that my kid stayed up so late in the evening. Then I found that I was not alone. I spoke with other moms who were in my same boat and I began to feel more normal. Perhaps my son's body had its own internal clock that was set similar to my own rather than to kid time. I did, however, continue to feel a bit ashamed to still be using his swing. I mean he was four months from being two and he was still using a swing to take naps and get to sleep at night? No bueno. This continued until we had the baby and moved into our new home.
Once we moved, I explained that the swing was now for "E" and we would have a new routine for going to sleep. I started with bedtime. I began rocking with "O" in his bedroom (this was key: the rocking chair didn't fit in the bedroom in our apt. so it was in the living room) and immediately we saw a difference. The first few nights I explained to him that he was a big boy now and big boys go to sleep in their big boy beds awake and stay there until they fall asleep etc. I explained that I would be in the other room and would come back to check on him. He willingly went into his bed and for about a week stayed there..... all night! I was ecstatic!
Then we went through a testing phase.