What is it with guys and asking about weaning? Joe used to, until I schooled him on the recommendation of 2 years by the WHO (and soon to be AAP hopefully), and Josi showed problems with cows milk. Ugh. Sorry, just annoyed with that question on my end here.
I would have to say that you will do fine at your thing. Take the pump, and Dean should be fine too. I'm not sure about going away, it shouldn't be a reason to wean anyway. You can always take the pump, just try to coordinate his nursings to where it would be convenient to pump while gone. I personally can't leave my kids this young, but I am not comfortable that way. Loralei stayed away from us for the first time, a night when she was 2 and I.did.not.sleep. It's gotten better, but it really only got better for
me after Josi was born and I had her with me. I don't know what I'll do when they grow up

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Maybe suggest to DH that you'd rather go somewhere later on in the year, like fall/winter time. That gives you time to plan it out and work on his nursings to make pumping while gone work.
I really really could use a night just myself and DH at this point, but we are too broke

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