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DH is awesome with the kiddo. He loves her, he loves to play with her, make her smile, make her happy, ect...

He cannot handle her crying. When DD cries she is very high pitched and it really disturbs him. Ive told him, "take a deep breath, figure out what she needs". His usual answer is , "she wants to nurse". He works a lot, and I am at home, so I havent been pushy at all about him taking care of her. He has watched her 4 times since she has been born. Never for more than an hour. During the past two weeks, DD has been going longer and longer between feedings and she is taking some solid food. (really, maybe 8 oz per week of solid food, but the new tastes make her happy and keep her from crying. She likes to suck on things like apples, peaches, ect.)

So thats a little backstory. Today DH asks me very nicely if I mind if he goes to the outhouse race tomorrow. (in my mind Im thinking, "why are you asking if I mind if you go somewhere?) I told him I didnt care. Last year he was gone for 5 hours when he went. Then he says, "I would like to take Ada with me." I cant go. We have a retail business , so someone has to stay here. So, he is going to take her away. For five hours. I told him yes.

Help me please:
How do I make sure that this is a great experience for everyone?

What should I pack for him to take without him feeling like he has to take half the house anytime he takes his kid anywhere?

How many times is ok to call without him feeling like Im hovering or dont trust him?

Is it ok to call a friend who will be there to get him to take pictures of DD's first day out with Daddy?

I am really nervous. He is a good dad, someone please tell me she will be fine. What are your experiences with your childs first time away with Dad/ Dad's what are your first experience out with your kid?