He figured that she could follow it. He's given her the chance to raise the stakes as she likes - and she gave him a set up. He's just seeing where she'll go with this.
Regardless, he's going to get very familiar with seeing a lot of her, literally and figuratively.
"So out of curiosity... what are we going as for Halloween, since we're doing the same thing either way, and I should get familiar with it. And is the obstacle course ready? Oh, and when you answer those two questions, I have one more question for you."
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