porkypig
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If he can talk and understand you, I'm not sure I'd do cry it out. Only because he has a means now of communicating and Jacob would cry ALL night until we went!!
We ask Jacob what is wrong. But we have to take him out of his room and sit on the landing and calm him down first. Once we've listened to him and done whatever he needs, he does tend to settle straight away (you may have to repeat yourself).
Don't get me wrong he will paddy and have wants that we won't allow but we try to steer the conversation away as in, go back to sleep because in the morning we're doing x, z, y or peppa pig/fireman sam are still in bed asleep if he wants to get up When he says he wants to get in our bed, we say no back to Jacobs bed and just keep taking him back. (wrongly though I do sometimes give in )
I do think though that when they are learning something new, they do tend to wake up in the night. How long has he been doing it for?
Hes been like this for months but as of late its got worse-maybe there's some truth in what yoy say as his speech is really coming on at the mo, but i also think it might be his last set of teeth coming through so it could also be this Xx