First choice would be Catbeard. He has excellent taste and a hunger for the finer things in life, so I feel he could take us to a nice restaurant for an excellent meal.
Second choice would be Blind Mew. If we were eating at a place on Skull Island, I'd need his enhanced sense of smell to make sure there was nothing shady about the food we were about to eat. Plus, I have some story questions for him.
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Bonnie Anne without a doubt! Well, her or Gracie Conrad. XD
Bonnie is my first choice because she's an interesting fox, and I'm certain she has a lot of interesting things to talk about, I mean, if she's comfortable talking about her past and stuff. And she's my favorite companion.
Gracie is my second choice because she's so cool. I've always loved her and had an interest in science and hydraulics, so I imagine we'd chat about that the entire time. XD