Dash & Lily Books in Order

The Dash and Lily books are holiday rom-coms with a little extra bite. The basic appeal is simple: put two very different teenagers in New York City at Christmas, give them a red notebook full of dares, and let the city do half the flirting.

Dash is sharp, skeptical, and a little too pleased with his own cynicism. Lily is hopeful, impulsive, and all in on the magic of the season. In Dash & Lily's Book of Dares, they get to know each other by leaving messages and challenges in a notebook passed back and forth through bookstores, neighborhoods, and chance encounters. A lot of the fun comes from how well they connect on the page before they have to deal with real-life chemistry.

New York matters a lot in this series. The books love crowded sidewalks, independent shops, snow, decorations, and the sense that a city can turn into a scavenger hunt if the right person sets the rules. That holiday setting gives the first book its charm, but it also keeps the later books grounded. These stories care about place, tradition, and the way a season can intensify everything.

The sequels let the relationship grow up a bit. The Twelve Days of Dash and Lily checks in after the first glow has faded and Lily is struggling after her grandfather’s health crisis. Mind the Gap, Dash & Lily pushes the couple into long-distance trouble when Dash heads to Oxford and Lily stays in New York, then reunites them in London with predictable and very human complications.

So while the trilogy starts as a cute opposites-attract setup, it does not stay shallow. It becomes a story about how two people keep choosing each other when life is less tidy than the fantasy version. Expect warmth, banter, family side characters, seasonal mood, and a relationship that stays funny even when it gets a little bruised.

If you want the most festive place to begin with Levithan’s collaborative work, start with Dash & Lily's Book of Dares. If you already know the couple, the later books reward reading in order because the emotional beats land better when you have seen the spark that started it all.