Books About Separation Anxiety

The Best Separation Anxiety Books for Kids

Looking for excellent children's books about separation anxiety? This collection brings together Bookroo's highest-rated and most useful picks in one place.

Start with our editorial favorites, then browse recommendations organized by reading stage to find the right book for your reader.

The Shortlist

Our 10 Favorite Books About Separation Anxiety

Princess Posey and the First Grade Parade

Sale price

$1248

Chapter Book · Ages 5–8 · 2010

Princess Posey and the First Grade Parade

By Stephanie Greene, Stephanie Sisson (Illustrator) · Book #1 in the Princess Posey, First Grader series

A first grader faces her fears without her magical tutu. Can she find courage within?

96 pages· 2,627 words· Est. 30 min read

4.1/5 Goodreads · 843 ratings

$12.99Save 4%

Summary: Posey dreads her first day of first grade, especially without her confidence-boosting tutu. Alone, she must brave the daunting Blue Hall. But when she inspires a parade where kids wear what comforts them, school suddenly seems less scary. Will Posey discover her inner strength and charm her way through this new adventure?

Sale price

$1348

Picture Book · Ages 3–6 · 1983

Alfie Gives a Hand

By Shirley Hughes · Alfie series

A nervous boy attends a party alone and discovers unexpected confidence.

32 pages· 1,118 words· Est. 9 min read-aloud

4.2/5 Goodreads · 320 ratings

$13.99Save 4%

Summary: Alfie is thrilled yet anxious about attending Bernard's birthday party by himself. As he navigates the excitement and challenges of the celebration, Alfie learns he can enjoy himself without his comforting blanket. Along the way, he discovers newfound confidence and even makes a new friend. Will this experience change how Alfie views his independence?

Sale price

$1899

Picture Book · Ages 4–8 · 1993

Owen

By Kevin Henkes · Owen series

A boy must part with his beloved blanket as school looms. Can a compromise be found?

Caldecott Honor (1994)Boston Globe–Horn Book Honor (1994)

32 pages· 473 words· Est. 4 min read-aloud

4.3/5 Goodreads · 18,076 ratings

$19.99Save 5%

Summary: Owen's fuzzy yellow blanket is his constant companion, but with school approaching, his parents and Mrs. Tweezers insist it's time to let go. Despite their creative attempts to separate him from Fuzzy, Owen remains steadfast. As the first day of school nears, Owen's mother devises a clever solution that satisfies everyone. Will Owen find a way to keep his cherished blanket close, or must he face school without it? Discover a heartwarming tale of compromise and the comfort of security objects.

Sale price

$958

Picture Book · Ages 4–8 · 1993

Arthur's Family Vacation

By Marc Brown · Arthur series

Rain ruins vacation plans, but Arthur finds unexpected fun in Gatorville.

32 pages· 903 words· Est. 7 min read-aloud

4.2/5 Goodreads · 1,535 ratings

$9.99Save 4%

Summary: When rain threatens to wash away his family's vacation, Arthur steps up to save the day. With plans drenched, he discovers Gatorville, a place full of unexpected adventures. Can Arthur turn a soggy trip into a memorable family experience? Join him as he navigates the challenges of a wet vacation and uncovers the joys hidden in the rain.

Sale price

$1797

Picture Book · Ages 2–5 · 2015

Llama Llama Gram and Grandpa

By Anna Dewdney · Llama Llama series

A young llama spends the night at his grandparents' house for the first time.

40 pages· 320 words· Est. 3 min read-aloud

5.0/7 Bookroo experts·4.2/5 Goodreads · 1,796 ratings

$18.99Save 5%

Summary: Llama Llama is thrilled to spend his first night away at Gram and Grandpa's house. As he packs for the adventure, he ensures nothing is left behind. But when bedtime arrives, he discovers Fuzzy Llama is missing. How will he sleep without his beloved companion? Grandpa Llama steps in with a clever solution, turning a potential disaster into a night of sweet dreams. Will Llama Llama find comfort in this new experience?

Sale price

$1697

Picture Book · Ages 4–7 · 2018

Don't Forget Dexter!

By Lindsay Ward · Book #1 in the Dexter T. Rexter series

A toy dinosaur fears being replaced and seeks help to reunite with his friend.

32 pages· 442 words· Est. 4 min read-aloud

4.1/5 Goodreads · 2,657 ratings

$17.99Save 6%

Summary: Dexter T. Rexter, a confident toy dinosaur, faces his worst fear when left behind at the doctor's office. As panic sets in, he wonders if his friend Jack has found a new favorite. Dexter's antics, from singing their special song to seeking the reader's advice, reveal his determination to reunite with Jack. Can Dexter prove he's irreplaceable with his stomping, roaring, and chomping? Join this hilariously anxious dinosaur on his quest to reclaim his place in Jack's heart.

Sale price

$1597

Picture Book · Ages 4–8 · 2015

Dad's First Day

By Mike Wohnoutka

This book is about nothing.

40 pages· 310 words· Est. 3 min read-aloud

3.9/5 Goodreads · 460 ratings

$16.99Save 6%

Summary: Oliver is thrilled for his first day of school, but his dad is not. As excitement turns to nerves, Oliver wonders if staying home might be better. Can Oliver convince his dad that school is the start of an exciting adventure? This heartwarming tale explores the mixed emotions of new beginnings, capturing the essence of change for both children and parents. Will Oliver's enthusiasm be enough to ease his dad's worries, or will they both discover something unexpected about the first day of school?

Sale price

$1697

Picture Book · Ages 4–8 · 2019

Truman

By Jean Reidy, Lucy Ruth Cummins (Illustrator)

A small tortoise named Truman embarks on a journey to find his owner Sarah after she leaves him behind.

Charlotte Zolotow Honor (2020)

48 pages· 526 words· Est. 5 min read-aloud

4.8/7 Bookroo experts·4.3/5 Goodreads · 2,008 ratings

$17.99Save 6%

Summary: Truman, a tortoise, lives high above the bustling city with his best friend, Sarah. When she leaves for school, Truman faces the unknown as he ventures across the living room. Can he find the courage to reunite with her? As he navigates this new world, Truman discovers bravery in the most unexpected places. Will his determination lead him back to Sarah, or will the journey prove too daunting? Join Truman on this heartwarming adventure of friendship and courage, where even the smallest steps can lead to the greatest discoveries.

Sale price

$1899

Picture Book · Ages 2–5 · 2005

Llama Llama Red Pajama

By Anna Dewdney · Llama Llama series

A baby llama waits for his mother to come back to bed.

40 pages· 235 words· Est. 2 min read-aloud

4.8/7 Bookroo experts·4.3/5 Goodreads · 54,745 ratings

$19.99Save 5%

Summary: Baby Llama's bedtime becomes a whirlwind of worry when Mama leaves the room. As his soft whimpers escalate into cries, will Mama return in time to calm his fears? This rhyming tale captures the universal need for comfort and reassurance, resonating with both children and parents alike. Discover how a little patience and a lot of love can turn bedtime drama into sweet dreams.

Sale price

$1398

Picture Book · Ages 3–6 · 2016

Bear's Big Day

By Salina Yoon · Found series

Bear's first school day tests his independence without his beloved bunny.

40 pages· 267 words· Est. 3 min read-aloud

3.8/5 Goodreads · 406 ratings

$14.99Save 7%

Summary: Bear embarks on his first day of school, determined to be grown up by leaving his stuffed bunny, Floppy, at home. But the day doesn't go as planned, and Bear discovers that growing up doesn't mean abandoning what he loves. Will Bear find a way to balance independence with comfort? Join Bear and Floppy in this heartwarming tale of new beginnings and cherished friendships.

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