Answer:
He asked her out. Afterwards, on their date at the diner, Holling told Meryl Lee about his dad's architectural plans for the new design of their school. Later, when Meryl Lee innocently tells her dad about Holling's dad's design, Meryl Lee's dad steals the design and presents them as his own at a meeting at Meryl Lee and Holling's school. This creates a rift between Holling and Meryl Lee (for a while, anyway).
Explanation:
If you're talking about Holling and Meryl Lee from "The Wednesday Wars," this is your answer.
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