Holling's problem is that he doesn't have enough money to take Meryl Lee, his crush, someplace nice for their Valentine's Day date. His shortage of funds is no joke: he literally has only has $3.78. Wondering where he can possibly take Meryl that will be fun (and impressive), Holling consults his sister as well as his friend, but they only make him feel worse, reminding him that he'll look like a cheapskate if he doesn't pull off a good date.
Mrs. Bigio solves Holling's problem for him, offering him two free tickets to see Shakespeare's Romeo and Juliet on stage. It's a perfect solution. Holling already knows that Meryl likes Shakespeare, particularly this play, and it's a love story--just right for a date, especially a Valentine's Day date.
Mery loves it, and Holling still has enough money to take her to Woolworth's after the show and buy a Coke for each of them. The date is a success: Holling describes the whole thing as "swell," hopes that Meryl's dad will forget to come pick them up, and notices how her auburn hair shimmers under the lights of Woolworth's.
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