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Technically, he and Juliet first meet IRL when she arrives on Guernsey island and asks him where she might find a room to stay for the night, and he nearly kills her by dropping tiles from the roof he's repairing on the street next to her. Naturally, they don't realize who the other actually is. It's not until the pair meet at the book club meeting that night that they truly make a connection; they admit later on in the film that they each expected the other's physical appearance to be far different (in Dawsey's case, he envisioned her as a rotund, tweed-loving grandmother). The cutest of meet-cutes.