Dai Monday Books in Order
Part ofJenny O'Brien Books in OrderThis page shows the Dai Monday books by Jenny O'Brien in order, with short summaries, series background, and helpful advice on where young readers can begin.
Last updated: July 14, 2026
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Dai Monday books in publication order
2 books
Boy Brainy
by Jenny O'Brien
2016
Bullied Dai Monday thinks his name is trouble enough, until a mystery at Conwy Castle draws him into a hunt for King Arthur's crown. With crooks, ghosts, dragons, and magic in the way, Dai must find his courage.
Granny's Gone AWOL in Guernsey
by Jenny O'Brien
2018
Dai Monday's purple-dreadlocked, Harley-riding Granny Gosh has disappeared in Guernsey. With his best friend Win and the interfering ghost of King Arthur, Dai sets off on a funny, magical hunt to bring her home.
Dai Monday books in chronological order
Series background & context
The Dai Monday books are middle-grade adventures for readers who like school worries, oddball grown-ups, legends, ghosts, and a little bit of magic mixed into everyday life. Dai is a boy with a memorable name and a tough problem at school: he is being bullied. That emotional starting point gives the stories a real feeling beneath the jokes and wild adventures.
Dai is not presented as a flawless hero who has every answer ready. He is young, worried, and trying to figure out how to deal with people who make school miserable. But he is also curious. Once a mystery appears, he is prepared to ask questions, take risks, and keep going when the sensible option might be to stay home.
Things get strange quickly.
In Boy Brainy, Dai's troubles lead him toward Conwy Castle and a hunt connected to King Arthur's crown. The book brings together bullies, crooks, ghosts, dragons, and Welsh history in a fast-moving adventure. Dai has to face the people making his life difficult while also deciding what kind of friend, son, and brave person he wants to be.
The series has a playful fantasy tone, but it does not talk down to its readers. Dai's worries about fitting in, being embarrassed, and getting through school are treated seriously. The magical side of the story gives him a way to step outside those daily problems and test himself in bigger, sillier, and sometimes scarier situations. The result is an adventure with plenty of jokes and chaos, but also a gentle message about self-worth.
Guernsey becomes important in Granny's Gone AWOL in Guernsey.
The second book reunites Dai with his best friend Win when Dai's grandmother, the spectacular Granny Gosh, disappears. She is not the kind of granny who quietly stays home. With purple dreadlocks, Doc Martens, and a Harley Davidson, she is already a force of nature before the mystery starts. Dai and Win head off on a search that brings back the ghost of King Arthur and opens the door to more folklore and magical trouble.
Friendship is central to both books. Win is not simply a sidekick who agrees with everything Dai says. The pair have to cooperate, cope with adult confusion, and make choices when there is no obvious way forward. The stories also make room for family relationships, especially the bond between Dai and the adults whose unpredictable behaviour can be both embarrassing and helpful.
These are short, lively books with a mix of Welsh and Irish legend, local history, and comic adventure. They suit confident younger readers, read-aloud sessions, or children looking for a funny mystery with a hero who feels more ordinary than the situations around him. Start with Boy Brainy for Dai's first big adventure, then move on to Granny's Gone AWOL in Guernsey for a larger family mystery and another dose of Arthurian mischief.
Edited by
Software engineer whose passion for tracking book recommendations from podcasts inspired the creation of MRB.
Lead investor at 3one4 Capital whose startup expertise and love for books helped shaped MRB and its growth.

















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