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Cover of Molly, Olive and Dexter: The Guessing Game
Picture · ages 2–5

Molly, Olive and Dexter: The Guessing Game

Written and illustrated by Catherine Rayner

Book 2 of 4 in Molly, Olive & DexterView the full series

Part of the Catherine Rayner universeOpen the collection

Endlessly rereadable

A soft, funny friendship story about guessing games and realising that friends may think differently from you. Lovely for preschoolers learning turn-taking, patience and social imagination.

  • Best for2–5
  • FormatPicture
  • Length32 pp
  • Read aloud~6 min
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The vibe

What it’s like.

Style

  • Conversational
  • Repetitive
  • Comedic

Tone

  • Gentle
  • Warm
  • Funny
  • Cosy
  • Heartwarming

Themes

On the pagefriendship, guessing game, play, owl, different thinking, turn taking, fox, hare

Experience meters

Energy2/ 5
Humour2/ 5
Scariness1/ 5
Peril1/ 5
Wonder3/ 5
Cosiness5/ 5
Emotional intensity1/ 5
Conceptual intensity1/ 5

What’s it about?

The story.

Olive the owl loves guessing games, so Molly the hare and Dexter the fox decide to play one with her. At first the game seems simple enough, but when it is Olive's turn, her friends cannot work out what she is thinking about at all. The fun lies in the gap between what one friend imagines and what the others expect. This second Molly, Olive and Dexter book gives Olive the spotlight, using a very small game to explore a useful social idea: friends can see the world differently, and that difference can be charming rather than frustrating. The story is gentle, short and emotionally safe, with just enough comic puzzlement to keep toddlers involved. Rayner's artwork gives the trio warm personalities and a soft woodland-garden world that feels comforting and familiar. It is especially useful for shared reading about listening, guessing, taking turns and understanding friends.

Fit check

Right for your child?

Where it lands by age

  • 1
  • 3
  • 5
  • 7
  • 9
  • 11
  • 13
  • Best fit · 2–5
  • Read aloud · 2–6
  • Independent · 5–7

Prose load

Light

Visual support

Very high

Reluctant-reader friendly

Very

Read-aloud quality

Excellent

Works well for

  • Reading aloud
  • Bedtime
  • Reading together
  • Reluctant readers
Low sensitivityNo content warnings

Nothing in the book is likely to concern most parents. Safe to recommend without preview.

Bedtime suitability

5 / 5 · Bedtime-friendly

Sensitive-child

5 / 5 · Good fit

Graphic intensity

1 / 5 · None

Best for

  • Toddler friendship
  • Guessing games
  • Gentle bedtime
  • Animal friends
  • Beautiful illustrations

Avoid if

  • Wants high energy plot
  • Wants laugh out loud funny
  • Needs older picture book

Particularly good for children who are…

  • Making friends
  • Starting nursery or preschool
  • Bedtime battles
  • Neurodiversity or learning differences

In the classroom

How it works in school.

Gentle, warm read-alouds about friendship and belonging for the very young — lovely for joining in and talking about kindness.

Classroom role

  • Read aloud
  • Discussion and empathy

A book children love that happens to support school — never a stand-in for the texts a class is taught with. Reviewed for the classroom · June 2026.

Why it lands

Why they love it.

Why kids love it

The specific delight is Olive's turn — guessing games working fine until Olive is up, then Molly and Dexter completely unable to work out what's in her head. The Catherine Rayner toddler picture book on friends thinking differently and that being charming rather than annoying.

  • Friendship and belonging
  • Animal companions
  • Trickery and cleverness

Why parents love it

The second Molly Olive and Dexter — Olive in the spotlight, social-imagination and turn-taking as the gentle theme. Same soft woodland-garden world. Useful shared-reading for listening, guessing and understanding-friends-think-differently.

  • Beautiful illustrations
  • Bedtime appropriate
  • Quick to read
  • Nostalgia

In the series

Molly, Olive & Dexter.

4 books · open the series →

About the author & illustrator

Catherine Rayner.

CR

Catherine Rayner

Writer & illustrator · United Kingdom · b. 1976

Catherine Rayner is a British author-illustrator born in 1976, whose painterly, watercolour-textured picture books have become a quiet staple of the gift-shelf end of UK children's publishing. She won the Kate Greenaway Medal in 2009 for Harris Finds His Feet and has been a Greenaway shortlister several times since. Best known for Augustus and his Smile, Harris Finds His Feet, The Bear Who Shared, Smelly Louie, Arlo the Lion Who Couldn't Sleep, and the Molly, Olive and Dexter early-reader series. Rayner's work is gentle, emotionally observant and visually distinctive, her animals are loose-brushed and full of feeling rather than slickly drawn. Strong read-aloud and bedtime quality for ages 2–6.

More from Catherine Rayner

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Lateral matches. Same shelf, different texture.

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Last reviewed · April 2026Suggest a correctionHow we recommend

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