Alex and the Ironic Gentleman (Series) by Adrienne Kress - 9/10

In these parallel adventures, daring Alex learns to balance adventure and morality and cynical Timothy discovers that some things are worth fighting for.

Each book follows the titular character as a life-altering experience compels them on a quest where they meet casts of eccentric figures; Alex is on a quest to rescue a friend who has been kidnapped by ruthless pirates and unearth a legendary treasure - Timothy must free a dragon who has been magically bound into human form. Along the way, they each learn about loyalty, bravery, and what matters most.

I found Alex to be more immediately likeable - she is a strong, independent heroine who is quick to rise to adventure and press forward even when things get difficult, making lots of friends along the way. Timothy is prickly, bordering on apathetic - too smart for school and not sufficiently supported at home - but this makes his journey and story arc stand out more (there's also the chance that he would appeal more to a teenage audience).

*The characters in this book are middle schoolers, but the themes explored - especially in the first book - are quite heavy. Alex's quest begins when her uncle is murdered, and part of her journey is dealing with that grief - and the pirates who killed him aren't done there. There is also an extended reflection on morality and law - which is not dark so much as highly conceptual. I think that Kress does a pretty good job of working complex themes into the story so as to show rather than tell, but it still makes the books a bit more mature. (Plus, ALL the other characters are adults...)

**In line with trends in the genre, Timothy pursues adventure by running away from home (he so, I suppose, does Alex, though she does so in search of her proxy guardian). While this extreme action is the catalyst for his family's ultimate reconciliation, it's still not a great example.

***Alex and cast turn up about halfway through Timothy's story, which is why these books are linked a "series" rather than standalone novels, which is relevant because it doesn't make a ton of sense to recommend just Timothy's story as more age-appropriate.