It’s Christmas in New York City in a pre-COVID world. The streets are busy, the lights are bright, and everything is decorated in holiday cheer. Lily is here for it. Dash is not. We open with a voiceover. Lily declares the holiday season the most wonderful time of the year. I happen to agree. If magic could wash over you, brush against your skin, I think it would feel like the holiday season.
Dash is the Grinch, nursing heartbreak. He’s down on love and Christmas. With a mother that picked Hawaii over him, he’s feeling a bit abandoned. It’s clear Dash is a lonely rich boy. And by the looks of his coat, he attends Dalton School or Horace Mann or Trinity School not on a scholarship. To cope with his broken heart and abandonment issues, he seeks out his place of refuge— Strand Book Store. While browsing the shelves, Dash discovers Gabriel Garcia Marquez’s biography not simply placed incorrectly alphabetically, under ‘M’ instead of ‘G’, but in the wrong section, fiction. After giving the annoyed clerk a brief education, he returns to his browsing only to find a red Moleskine notebook in the fiction section. I much prefer the Ocean or Reef colored Moleskine, but red is flashy, so I get it.
Brandishing the red notebook, Dash returns to the Information Desk, but the clerk is done with Dash’s know-it-all missives and ignores him. As he’s about to discard it on a cart of books waiting to be shelved, he notices the cover. And the challenge—”Do you dare . . . ?”
Inside the notebook he’s offered a choice. Either follow the clues to reveal the secret message or put the book back on the shelf. He turns the page. Our Dash has found a cure for his holiday blues, so let the games begin. Just as he’s about to use his phone to decipher the first clue, the notebook warns that using the Google is for lesser humans. Humans unworthy of the notebook. Did anyone else catch the James Patterson shade? I chuckled a bit then felt guilty because I was sure Mr. Patterson was about 100 years old. He’s not. I was off by some decades.
While on his scavenger hunt, Dash runs into his ex’s best friend, Priya. She, with a tone of resignation and mild hostility, invites Dash to her Christmas party, attempting to lure him with the return of Sofia. She is likely the ex. He’s holding The Joy of Gay Sex by Charles Silverstein and Edmund White, which gets an eyebrow raise and a question from Priya. Dash’s response, “tell her I’m trying new things,” is perfectly delivered. I want to be his friend.
After completing the scavenger hunt, Dash takes on the next challenge—“Are you brave?” An impromptu open mic night at the Strand is what comes next. He shares a dramatic reading of “River” by Joni Mitchell, which is one of the saddest Christmas songs. And it isn’t even saved by the jaunty beat of a “Last Christmas.” It’s just sad. Before Dash can make his way through the entire song, the nameless clerk from the information desk pulls the plug and tells him he has the final two words of the clue. The secret message is complete—“Are you going to be lonely on Christmas?” Instead of responding and placing the notebook back on the shelf, Dash carries it out of the store. The once dragging feet now have a bit of pep. And Dash does what any of us would do, he’s off to share with a friend, Boomer.
Boomer is pure sunshine. And he works at Two Boots. Two Boots like Strand Bookstore is an institution. The Strand has a few decades on it, but both are beloved. Yes, Dash & Lily is a love story, but it’s also a salute to New York City. Maybe even a love letter to the city. Anyway, tamping down my nostalgia . . . Dash does what you do with friends, he recounts the strangeness of his day. The notebook and the mysterious girl that intrigue him. Boomer realizes he likes Clue Girl, so Boomer and Dash concoct a plan, a sting operation. As someone who, on more than one occasion, helped a friend stakeout a college dorm, I know there is a high failure rate when sting operations are conducted by amateurs.
Leaving Boomer, but with the gift of pizza, Dash heads to his dad’s place. Dash helps himself to a little brandy. No chance of Dash’s dad catching him since we learn that dad, like his ex-wife, has abandoned Dash for the holiday break. Dash let’s us in on his secret. Dad thinks he’s with mom. Mom thinks he’s with dad. And his friends, save Boomer, think he’s in Sweden. He profoundly declares that he’s given himself the gift of solitude. I love this kid. A lonely Dash lets his mind drift to happier times. We flashback to Sofia and Dash sprawled on the piles of coats atop the bed at a party. It seems a sweet and romantic scene, but we learn that distance is what tore them apart. She’s in Brazil. Rather than drown in sad memories, he turns to the notebook and writes about how the holiday season makes him feel. How it really makes him feel. I’m not sure how well his “bah humbug” will go over with Lily, the Christmas elf.
Dash leaves the notebook and directs her to Boomer and Two Boots. Sting operation activated. In the middle of a crazy lunch rush, Boomer misses her. And she’s on to Dash and the trap he tried to spring. So now he must pay. She’s going to make him work for her name.
We aren’t privy to the dare but whatever happened resulted in Dash being escorted from Macy’s by a security guard and a super sassy elf. He also escapes with Santa’s hat. Dash may be on Santa’s naughty list, but it was worth it. He knows her name— Lily. We rewind to the beginning, it was Lily that ran into Dash, but we knew that. And the voice he heard rising above the other carollers? That was Lily too. Usually I hate coincidence, but this one is so sweet.