[Hmm. That question doesn't really parse. Still 1.]

Are you... her?

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apples & oranges illustrator detail - very simple.

hmm that question doesn't really parse. apples and oranges - I thought it maybe fun to combine the two into one fruit to make it even more ambiguous like a hint from the previous question "are you helping her to find me?" as if apples and oranges are actually the same as are the two subjects in his question.

Round peg - square hole/square peg - round hole, yada yada... but as an exclamation point! (!) not sure why, maybe the round peg is curved to look more like a question mark. (?)

Russian nesting doll opens to reveal a box inside as a reference to the box being a daughter (of God) and container like a box also the woman image painted on the nesting doll could be holding a box so that when the doll is opened so is the box, a fun nod to the movie within a movie as this is all being illustrated on the side of the live action box talking with Buffalo Joe as if to say when the box is opened an equal reveal will be made and likewise if the illustrated box within the nesting doll is opened there maybe another nesting doll -- turtles all the way down, my friend.

"Are you her?" Box face lower right, could be done more beautifully and enhanced to make her hair look even more like a question mark (?).

The upper left image is a sort of network tree drawing (unequal) or invalid conclusions. The circles could be filled with fun images to make this idea stronger, I'm imagining evolutionary lifeforms or even scientific scholastic images like atoms, infinity symbol, DNA, cell division, pinkfloyd prism, crystals (geology), ape>man (evolution), x/y graph with parabola or wave function, sacred shapes (geometry), sky chart (astronomy), great year wheel (astrology), beakers of potion (chemistry).

"doesn't parse", round pegs going in square holes, cylinders that don't fit into boxes.

a box that doesn't fit into a circular hole

Boxes bouncing off the Kline bottle, they don't fit