Especially/with the whole family

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Rachel Adams

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Is a comma required after "especially" and is "with your whole family" idiomatic than "with the whole family"?

I love Halloween. Especially(,) I love to carve a pumpkin. This activity is very exciting if you do it with the whole family.

Context: I provided the other sentences for context. I am saying that I enjoy carving it with my children who enjoy it too.
 
Prefer:

I love Halloween! I especially like carving pumpkins, which is the most fun if you do it with your whole family.
 
Prefer:

I love Halloween! I especially like carving pumpkins, which is the most fun if you do it with your whole family.
So "with your whole family" is more idiomatic than "with the whole family", isn't it? For example, "I usually have dinner with my/the whole family."
 
I don't find one preferable to the other. If you say "the whole family", no one is going to think you're talking about someone else's family, so it's the equivalent of saying "my whole family". However, I'd question the use of "whole" there. I don't think it's necessary if you're just talking about the people who live in your house.

I love carving pumpkins. It's great fun [to do] with my family.

If someone said to me "I'm having dinner on Sunday with my whole family", I'd assume they were talking about their parents, siblings, and maybe even more distant relatives (cousins etc).
 
So "with your whole family" is more idiomatic than "with the whole family", isn't it? For example, "I usually have dinner with my/the whole family."
I changed the word unconsciously -- not on purpose. Use either.
 
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