Your babe is just a day older than mine :)
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I started around 7 or 8 weeks with a bedtime routine, starting around 7:30pm- bath, massage, swaddle, nurse, and books if he was still awake. Up until last week, I could lay him down awake but drowsy, turn on his little musical seahorse, and lightly rub his face and "sshhh" and he'd fall asleep, and I'd head back downstairs until I was ready for bed. We haven't been able to pull that off since daylight savings, though... He was getting tired earlier, and it took us a few days of adjusting our routine, dinner, etc... We're now working on pushing bedtime back closer to 7:30 or 8, because I (or "we," he'll be coming with me) just got a p/t job and starting two weeks from now won't be home until 6:30 most evenings. But he's been waking up 20 minutes after I put him down, then he gets overtired and cries hard- and this is not a fussy baby- and it's been taking an hour or so of DH and I trading off to get him to sleep.
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I'm just trying, and really starting the past two nights or so, to be really consistent about calming him, putting him back in the cosleeper. He cries, I pick him up, calm him, put him back. It's eating up a lot of my evening, time with the husband, time to get stuff done, but I'm hoping it'll pay off.
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I started today having him nap in our room with lights off/curtains pulled, swaddled like we do for nighttime, instead of downstairs in the bright kitchen in his swing. I gave in this morning and napped with him in bed with me, and he slept for two hours, but he's just now waking up after a 30 minute nap up there alone. I guess I want to get him used to going to sleep that way, although when he's napping at work with me in a few weeks, I'm sure there'll be some adjustments.
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Sorry for rambling- I know that wasn't much help, since I still haven't figured this out on my own. Maybe it's the age? :)