It makes sense to compare a doll to youth and innocents which could be what her costume, Raggedy Ann, is referring to despite the serious situation.

Maybe this shows his struggle with the loss of his wife and the or maybe that he struggled with connecting with his kids and regrets not having that connection?

Sometimes a dialogue tag is unneeded because of clarity through context, meaning that the context of the conversation makes it clear who is speaking. This can appear in back-and-forth conversation between characters.

I can really relate to this because I spend so much time thinking about what I am going to write that it feels like the final piece when I'm done with it. Then it's hard to make new adjustments because I view it as done.