Dash & Lily's Book of Dares by Rachel Cohn and David Levithan

If you're looking for a Christmas pick, this clever NYC-based scavenger hunt is festive and heartwarming (and really funny), but never cloying.

Published December 13, 2024

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dash & lily

Novel: Dash & Lily's Book of Dares by Rachel Cohn and David Levithan
Release Date: October 11, 2011
Publisher: Ember
Format: eBook
Source: Bought

baby Grac
Baby Grace, posing with David at a book conference!
As I rebuild the WLS archive with books I've read from 2011 through to 2025, I want to build a fully-fledged ecosystem of books I've read and recommend. I'd like to be able to reference and speak to any I've finished. For books I haven't reviewed (or can't entirely remember), please enjoy this brief questionnaire that can help you decide whether it's a read you'd like to pursue. Some of these are favorites I just haven't gotten around to fully reviewing yet—I'll explain in each description, but I hope this Q&A can be illuminating to you in the meantime.

"I've left some clues for you.
If you want them, turn the page.
If you don't, put the book back on the shelf, please."

16-year-old Lily has left a red notebook full of challenges on her favorite bookstore shelf, waiting for just the right guy to come along and accept its dares. Dash, in a bad mood during the holidays, happens to be the first guy to pick up the notebook and rise to its challenges.

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What follows is a whirlwind romance as Dash and Lily trade dares, dreams, and desires in the notebook they pass back and forth at locations all across New York City. But can their in-person selves possibly connect as well as their notebook versions, or will their scavenger hunt end in a comic mismatch of disastrous proportions?

Co-written by Rachel Cohn (GINGERBREAD) and David Levithan, co-author of WILL GRAYSON, WILL GRAYSON with John Green (THE FAULT IN OUR STARS), DASH & LILY'S BOOK OF DARES is a love story that will have readers scouring bookstore shelves, looking and longing for a love (and a red notebook) of their own.


Why I Picked It Up

I actually vividly remember reading this book for the first time. It was winter exam week in the 7th grade (a few short months after I started this blog), I'd just finished Latin, and the policy was that we had to sit quietly in the hall until everyone was done, either reading or studying for our next. So I bought this one, which may have actually been my first David Levithan book. (I adore him, both as a writer and editor; he has a very crisp, precise, absorbing, and bittersweet voice that entirely aligns with my taste.)

I wouldn't say I normally read seasonal books because they tend to strike me as flat and saccharine. A Hallmark movie or read has a time and place, but I'll usually put them down and lose interest.

Anyway, Dash & Lily's Book of Dares is a triumph and a very special book to me. It's been awhile since I've read it (and I love rereading it around the holidays.) Usually, around December, I'm craving a snowy winter atmosphere in the likes of A History of Wolves by Emily Fridlund or Shiver by Maggie Stiefvater instead. But Dash & Lily is unafraid to lean into the seasonal aspects with unabashed cheer, and it's one of the only books to make me crack up entirely. (I did get shushed in the exam hall—and I was a kid who never made trouble!)

But in contrast, the book's not afraid to get serious or melancholy about the transitions and struggles of the holidays (and of growing up.) It was my first taste of Levithan's—and Cohn's, although I haven't read any of her single-author books—specific, piercing way of translating significant, sonder-like emotions. Middle-school friendly existentialism, but equally stirring for any age. It's complex but accurate, and wrapped up in a bow for you. (Sorry, had to.)

Related: The Dictionary of Obscure Sorrows by John Koenig (referenced in The Age of Magical Overthinking by Amanda Montell, which I just read) is now on my reading list too.

The book talks about the confusion and uncertainty of holidays changing for the first time, and it's also a love letter to New York City in December.

The (Oh-So-Lovable) Characters

Lily is sheltered and childlike and wondrous. She understands why she has a hard time with others (beyond her tight-knit family) but doesn't understand why she should have to change for social situations when she loves herself as-is.

Dash is "snarly," a descriptor which makes sense once you read the book. He's pretentious, but not overly so. He has walls up and strict assumptions, and he's also very anti-cheer. You just know he'd call everything "cringe," and that a Manic Pixie Dream Girl is very much his style.

And the cast as a whole is so flavorful. They each feel different and distinctive, and I adored many of them.

And So the Hunt Begins

The story begins with a little notebook tucked next to Franny and Zooey by J.D. Salinger at the Strand. (Also, this book was the reason I initially read Franny and Zooey in the eighth grade—which I loved and introduced to my teen book club in high school. A formative read!)

Immediately, the reader experiences the warmth and comfort of wandering through a cluttered bookshop on a chilly day. You could totally hear the bell ringing over the door, a flurry of snow melting on the door mat, a blast of soupy heat. A wind-red nose and hot chocolate may be involved. Already, this is a holiday win.

When Dash stumbles upon the notebook, he finds a challenge written in it from Lily, with the goal of (ideally) finding a cute teenage boy to be a romantic interest over the holidays. It's the analog equivalent of girls who post Google Forms to assess potential roommates and partners—a clear and effective way of wading through the muck. More power to them.

Basically, complete the challenge and Q&A, and it should be enough of a test to see if they would jive together. But instead of simply leaving his info, Dash decides to do the same: clues to a scavenger hunt, back and forth, all over the city.

The two get to know each other as pen pals.

All Hail Pen Pals

The pen-pal angle is one I'm especially fond of, especially in a longhand notebook instead of texting or "talking" online.

I had my own pen pal in high school and college, both craving the old-fashioned catharsis of letter writing, and we both agreed that it's sometimes easier to feel comfortable around those not in proximity to you. (Which—nonfiction rec—is a concept ironed out in You're Not Listening: What You're Missing and Why It Matters by Kate Murphy. We listen better to strangers because we don't make unconscious predictions or assumptions about what they'll tell us.)

For one, we were very similar—similar enough to gravitate towards the same correspondence style; for another, I've always valued the role of "out-of-context people" in allowing you to express yourself. If I know someone around me (who I don't really know that well) is going through it or maybe needs someone, I always make that offer. It's occasionally easier to talk through anything with someone who literally doesn't know you or feel connected; you might find yourself expressing thoughts and feelings you wouldn't have otherwise.

Dash & Lily Explore the City

Of course, the book is about the romantic arc and the holidays and all that. But the challenges and letters to each other peppered throughout the structure make it so much fun. The pacing flows effortlessly. You could devour the book in a night or return to it as a little treat; both experiences would be gratifying.

Like Dash having to ask for what he wants for Christmas on Santa's lap during a crowded department store situation with children. Lily dancing in her marionette boots with a Yiddish band. I loved Dash's complex relationship with his absent Dad, Lily's stubborn refusal to let go of her family closeness, the snarly Muppet, the greasy slices of pizza, Boomer's dialogue, etc,. So much to love.

These details will all make sense to you, if you read Dash & Lily's Book of Dares.

Cuffing Season, Perhaps? On the Romance

In Dash & Lily, there's of course the initial romantic interest. After a while, when Dash & Lily start to get closer, they also both worry that they've crafted a makeshift ideal in their heads. What if they meet and they don't live up to the "idea of" each other? In some ways, that initial friendship and connection makes it even harder to commit to dating each other and rock the boat, which is such a real (scary) concept when you go for it gradually, although slow-and-steady is so necessary to each of their styles.

The young, hip, online folks nowadays (God, that makes me feel old) will recognize some of the anxiety baked into that separation from the get-go—that "what if they don't like the real me once they know me?" feeling, and Lord knows you also get that feeling when in the early stages of dating.

Dash is quick to cut people off. Lily, despite her best efforts, sometimes occupies a dreamworld divorced from reality. Both have others tiptoeing around these feelings, and a lot to confront. Neither are wrong for their worldviews; they're just not universal, and cause their own challenges.

The one part of the book that really drives me up the wall (but also, conflict) is when Dash gets mad at Lily for getting drunk and kissing Edgar Thibaud. She was so clearly having an existential moment, but Dash doesn't know that because he doesn't actually know her. But for the same reason, he has no claim over what she can and can't do, and he's just looking to nitpick ways to not choose her. It just felt abrupt, but in fairness, it does illuminate Dash's character and judgmental tendencies in a realistic way. It's very honest about the troubles of a relationship rather than showcasing blind affection.

Overall Thoughts

In book clubbing this one, I'm realizing that there's so much about it that I love. It's so specific in a way that's carved out a hall-of-fame spot in my collection. Dash & Lily's Book of Dares pinpoints the joy and giddiness of the holidays, especially in New York City, in a way that other books fail to capture. It's also such a love letter to the city. You couldn't take this plot and plop it anywhere else, which is how you know the setting is a character itself (my absolute favorite quality.)

But it doesn't coast on atmosphere or nostalgia either, and you could absolutely read it whenever during the year, for other reasons. I find sometimes that "seasonal" books are pigeonholed into the holiday they're meant for. They're great "for a Christmas book" rather than simply great. Dash & Lily's Book of Dares doesn't have that problem. It's playful and Christmassy, but also knows when to balance it out with melancholy or friction.

I love the overview of course—the slow-burn romance that's rooted in friendship (very much my style), the well-rounded characters, the vivid language and clever cast—but the details are so wonderful and magical too. It's all the best for being lighthearted and meaningful, and showcases the articulate qualities of the author team.

The TV Adaptation Is in the Holiday Rotation!

If you've read and loved the book, the TV show on Netflix also does a lovely job in capturing the feel of the book, which is such a win in terms of adaptation. It knows what to exaggerate or cut for the same effect.

My family and I watched all eight episodes while playing with the babies and decorating at my sister's house in South Carolina the year it first released, and everyone loved it. I watched it again with a roommate I loved (miss you, Kira!) while living in Manhattan, which felt so right festivity-wise. I'll watch it again this season likely too, but I'm not sure when. As long as I watch It's a Wonderful Life, I don't care. But Last Holiday and Dash & Lily usually make it into the rotation too.

Also, in the pilot episode, they build a plot point around River, which has always been one of my favorite songs to listen to during the season (which very accurately captures the tone of each character's beginning "something's gotta give" state during the show.)

Dash & Lily is a good mix of indulgent and wholesome while still grounded in the whirlwind of a season and the tipping point of a given year, dredging up a lot of the emotion and reflection many feel around the holidays.

If you do want a more Hallmark-style piece of media though, I can make some suggestions there too.

The Rest of the Series

Eventually, Rachel Cohn and David Levithan released a sequel, The Twelve Days of Dash & Lily. Without getting into spoilers, the book itself is very different in tone—so I wouldn't reread it, although I'm grateful for the experience of having read it—because it's more about when a character feels like they've lost what makes them "them" and trying to get it back, and a partner in turn trying to support them/bring them back while still acknowledging the gravity of their change. So yeah, it's heavier, and more focused on when the holidays get hard.

There's a third book, Mind the Gap, Dash & Lily, which I frankly forgot about and haven't read. I should! It strikes me as being almost similar to the college-related conflicts of the third book in the To All the Boys I've Loved Before series by Jenny Han, and will undoubtedly resonate with kids experiencing those transitions. I am actually not sure whether this one is Christmassy or not.

For fans of:

When You Reach Me by Rebecca Stead; To All the Boys I've Loved Before by Jenny Han; Right on Cue by Falon Ballard; The Inheritance Games by Jennifer Lynn Barnes; Famous in a Small Town by Emma Mills; Book Lovers by Emily Henry; My True Love Gave to Me (YA anthology); Let It Snow (YA anthology); Fangirl by Rainbow Rowell.


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