We've co-slept with DS1 (5.5 y/o) for most of his life. When he turned five we began trying to get him to sleep the night in his own bed (this coincided with DH deciding he could no longer get a decent night's sleep with DS in our bed). We started by having one of us settle in with him, read, listen to relaxing music, etc., until DS fell asleep, then leave the room. We told DS he was free to join us in our bed if he woke in the night and couldn't fall back to sleep. He never made it more than a few hours on his own, and would come to us (usually crying) and need someone with him the rest of the night. While this was going on, I was progressing through pregnancy. By the time I reached the late stages, the arrangement had become: DH or I putting DS to bed, and DH spending the rest of the night in DS's room with him.
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DS2 arrived in December, and we decided to give DS1 some time to get used to his little brother before trying to persuade him to try sleeping on his own again. We talked to him about it, and started trying again a couple of weeks ago. There were two (exciting!) nights that he managed to sleep on his own until 5 or 6 a.m., but I've come to the conclusion that these were freak incidents that only occurred because he was *extremely* tired. He basically still wakes about four hours after going to bed, and needs someone to join him.
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Complicating matters is the fact that DS1 is afraid of the dark and a pretty sensitive kid. We've given him a sheep to cuddle with a lavender sachet that can be heated up at bedtime. We have a Twilight Turtle that projects stars on the ceiling as he falls asleep. He never falls asleep alone, and we leave the hall light on all night for him. Still, he isn't able to make it through the night. There isn't room in our bedroom for him to have a mattress on the floor, and now, with the baby co-sleeping, there isn't safe room in our queen-sized bed for mom, dad, infant, and extremely kicky 5 y/o.
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I miss sleeping with my husband, and he feels likewise, but I also understand that DS1 may feel left out with everyone else in one bed and while he sleeps alone. We've talked to him about this, but he insists that he *wants* to sleep alone, and he definitely doesn't want to sharing sleeping space with a crying baby, even if that were an option.
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One thing I think might help would be an earlier bedtime for DS1. He's homeschooled, so he doesn't have to get up super-early in the morning, but I know he's not getting enough sleep (9-10 hours/night) for his age. I'm pretty good at getting him to bed early enough, but DH isn't, so the bedtimes are inconsistent.
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Any other suggestions for helping DS with his fear of the dark and of sleeping alone? I don't want this to be a torturous process for him, but it's very clear to me that this isn't just a "phase" he'll be growing out of any time soon.
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(P.S. Here's something weird: We tried getting DS1 to sleep in his own bed when he first *got* a bed, at age 3.5. He not only went to sleep on his own, but stayed asleep on his own every night...for exactly one week. Never happened again after that )








 The little-by-little (bed, to chair, to door) approach sounds good--I think I'd heard of this before, but forgotten about it. Incentives also might help; DS is fairly goal-oriented, so having a little "prize" to work toward might give him that extra boost.
