In the meantime, guess what? Photos! At the pumpkin farm!
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You know how they say that in order not to overwhelm them, you should reduce young children's choices to two things tops? (For example: would you like the red cup or the blue cup?) Well, they're right, because, man, this is such a hard, painful decision every, single year.
We finally realized that he wasn't going to pick any of the pumpkins we suggested, so we tried covertly putting perfect pumpkins in his path and then "spotting" them. Didn't work. He had to find it on his own, and after looking over approximately 5,365 candidates, he wound up with the rinky-dinkiest pumpkin. But it was all his. And it was perfect.