How do I get my 17 month old to sleep and how do I know the difference between him waking to nurse/comfort and him waking because he's in pain?

My 17 month old has never been a great sleeper but he has been a better sleeper than he is now. He is still breastfeeding. He nurses before his nap and before bed. And on a good night, once a night. He sleeps in his own bed until we have a horrible night and I let him in our bed. Something else I might add is that he has had three ear infections in about 4.5 months (with constant head congestion the entire time), his last infection was diagnosed the 2nd week of January about 3 weeks ago. He hasn't been congested since but I am starting to see a little runny nose the past few days. He also has two of his two year molars coming in. I completely understand that all of these issues effect his sleep but I cannot survive on four broken hours of sleep a night. Typically a bad night goes something like this: He's in bed by 9pm, he wakes around 11:30-12. I nurse and rock him back to sleep and that can take anywhere from 45 minutes to an 1.5 hours. Then he wakes again about two hours later and we do that again. A really bad night (which happens about 2 nights a week, with 'bad nights' happening about 4-5 nights a week) he wakes around the same time and it takes me hours to get him back to sleep. Most nights it's around 2 hours but occasionally, like last night, it took me almost four hours. I nurse him, rock him get him to sleep, make sure he's good asleep.. lay him down and he immediately wakes up or lay him down and he's up within 10 minutes. Then we start over until he FINALLY goes back to sleep. Those nights he usually ends up in our bed and my husband ends up on the couch which we both hate. A good night he wakes up once, nurses and is back to sleep within 20 minutes. That might happen 1 night a week, if we are lucky. He can sleep through the night and after his last ear infection he slept through the night 4 out of 5 nights, then the bad nights started again. That leads me to feel that something is triggering these night wakings.... pain?? I don't know. I find myself really frustrated with him and I don't like feeling like that. I honestly don't know what to do. He takes good naps during the day. He goes to sleep within 15 minutes and usually sleeps 1.5 - 2 hours. I've thought about taking him back to the Dr to get his ears checked again but I don't want to be the over-reacting parent who comes in the office and all it is is teething. I do the teething tablets around the clock and on bad night I get the tylenol/ibuprofen out. I hate giving him the pain medicine though because I feel like I've already given him so much from all of the ear infections. There for a while I felt like I was giving tylenol/ibuprofen around the clock for weeks... so I just stopped, I just felt like it was too much. Other information: I have an older son who is three. He hasn't been sick at all but of couse his immune system is stronger. I stay at home with them, so they aren't in day care. They do go to the church nursery on Sunday's. I'm just exhausted and never had to deal with this with my first son. He was sleeping through the night at 10 months old and rarely had issues with waking unless he was sick and he always bounced back to his good sleeping habits. I just need some HELP!

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BTW, this is my, CrystalJ's,

BTW, this is my, CrystalJ's, question.