Dash feels bored with the world and “done” with relationships after a failed romantic entanglement. He wanders around in his favorite bookstore and complains to the management about finding a book miss-shelved in the wrong category, oblivious to the feelings of the person he is insulting (though he soon catches on). Once he finds Lily’s notebook, intrigued by the mystery she has set for him, he follows all the clues and has fun intellectually trying to figure out her puzzle and fill in the blanks. But he’s also not above “hacking” the system and trying to cheat, to satisfy his own curiosity – he wants to get help from the sales clerk, and then he asks his best friend to spy on the girl who drops off the notebook. When asked to choose between the two different Home Alone movies as his favorite, Dash points out that it’s impossible for anyone to visit all the places Kevin does “on foot” in New York in a single afternoon. Then he notices all the incredulous looks everyone is giving him and quickly declares that he loves the movie anyway. He doesn’t give much back in his relationships, though. He lies to his parents about spending time with the “other one” over Christmas so he can sit alone in his dad’s apartment and mope. It takes him wanting his friend to help him find Lily for him to show up at a concert. When asked to give his name, he gives her a mystery of her own – “I am a conjoiner of words” (Dash, which she does not figure out until much later). His best friend accuses him of conjuring up the “perfect” woman in his head and falling in love with that, rather than being willing to accept Lily for who she truly is. And it’s true, Dash has a romanticized ideal about her and when they finally meet face to face, and he finds her drunk and kissing someone else, he is willing to throw out everything they shared together and not bother getting to know her on a deeper level … at first. A week later, he has changed his mind. He is quick to puzzle out and solve the book challenge she sets for him in the red notebook and enjoys setting similar challenges for her. But… Dash is also somewhat stuck in his ways. He refuses to try new things and doesn’t want to eat new foods without prompting. He doesn’t go out of his way to explore tangible things, such as walking around the city and seeing the Christmas lights. He is somewhat hung up on his ex, bitter about all the rotten Christmases he has suffered, and assumes that other people should share his hatred of the holiday, because it has never treated him right. He shies away from telling his dad how he really feels about their relationship. But as he grows fonder of Lily, he starts being more open to doing things that ordinarily he would find abhorrent, because she wants him to, including making up for their fight by setting a romantic mood surrounded by all the things they shared together, even the super-salty pretzel he forced her to eat. Often, Dash starts to spill all of his feelings – about his dad, his ex, etc—in the notebook, only to change his mind and rip out the page.

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Dash is the ultimate loner who doesn’t care much if other people like him or not. He would rather spend Christmas alone in his father’s empty apartment than hang out with his friends or put up with the holiday cheer. He’s something of a Grouch (Grinch?) until Lily starts to thaw him out by forcing him to participate in holiday cheer and new things. He would stay home with his nose in a book rather than venture into a crowd. Dash loathes being around tons of people, and even hates the Santa Clause display in the big department stores. He also has a moody, self-absorbed side, determined to stay miserable. Dash will intentionally draw focus to the negative side of Christmas, to his own loneliness, to his hatred for the holidays, to his dislike of pedestrian people and things, and to his contempt for “normies.” But once Lily starts to brighten up his life, he starts to see that happiness is a choice.