Dash And Lilys Book Of Dares

Dash And Lilys Book Of Dares

book

2010, Fiction

WISE
89%

WISE Score

A charming, analog scavenger hunt through NYC that makes you want to leave a notebook in a bookstore and wait for a miracle.

Where to Read

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Screenwise Verdict

This is the ultimate 'comfort read' for a kid who feels a little out of step with the TikTok-paced world. It’s smart, funny, and celebrates the kind of creative weirdness that we want to see more of in the world.

While it was written in 2010, the core premise of an analog scavenger hunt feels even more refreshing today. It’s a great pick for a middle-schooler ready to move into YA territory without hitting the heavy trauma or explicit content that often comes with the genre.

Age Fit

Best for ages 12 and up. It’s a Young Adult novel that deals with teen identity and romance, but it’s relatively 'clean' compared to modern YA. Adults will also find it a nostalgic, cozy read.

WISE Breakdown
Wholesome
85

It’s a charming story about two teenagers connecting through shared thoughts and challenges rather than just looks. It captures the cozy, slightly magical feeling of New York at Christmas without being overly saccharine.

Imaginative
92

The central conceit—a scavenger hunt mediated by a red notebook hidden in the stacks of The Strand—is a brilliant invitation to see the world (and bookstores) as a playground for connection.

Safe
88

Standard YA territory. There is some mild swearing, mentions of teen drinking/parties, and typical adolescent rebellion, but it avoids graphic content or toxic dynamics.

Enriching
90

It’s a massive win for literacy and 'analog' living. It encourages creative writing, vocabulary (Dash is a bit of a word nerd), and exploring one's physical environment.

Parent Info

Why It Might Be Great

  • The Strand Bookstore setting is a dream for book lovers and makes NYC feel like a character in itself.
  • Dual perspectives allow readers to get inside the heads of both Dash (cynical, wordy) and Lily (optimistic, quirky) as they grow.
  • Analog connection over digital apps; it celebrates the slow burn of handwritten notes and shared secrets.
  • Holiday vibes that aren't just about consumerism, but about finding where you belong during the 'most wonderful' (and often loneliest) time of year.

What to Watch For

  • Dash can be insufferably cynical at first; it's part of his arc, but some readers might find his 'I'm smarter than everyone' teen energy grating.
  • Expect some mild swearing and references to teen drinking—nothing that isn't standard for a YA novel, but worth noting if your kid is on the younger side of 12.
  • There's a scene involving a 'Santa' underground party that gets a little chaotic, though it stays within the bounds of a PG-13 movie vibe.

Conversation Starters

  • "If you left a notebook in a bookstore for a stranger to find, what would the first dare be?"
  • "Do you think Dash and Lily would have liked each other as much if they had just matched on an app?"
  • "Which character do you relate to more: the one who loves the holidays or the one who can't wait for them to be over?"
  • "Why do you think it's sometimes easier to tell a stranger your secrets than your own friends?"

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