45 Books to Get Kids Through Life’s Trickiest Transitions

When words fail you—or your teenager tunes them out—it’s helpful to have someone else’s. “The beauty of books is that kids can be self-reflective, without the anxiety they might feel talking about their own situation,” says Pauline Jordan, Ph.D., a child psychologist in Greenwich, Connecticut. Consider this expert-recommended list a learning library for every age and stage.

New Sibling

Photo by Christopher Silas Neal

Olivia: A Guide to Being a Big Sister
By Natalie Shaw
Ages 3 to 6
Advice on sharing toys and lulling a baby to sleep from a familiar face—er, snout.

Henry Is a Big Brother
By Alyssa Satin Capucilli
Ages 2 to 5
A simple rhyming book that emphasizes patience. (Bonus: durable, coated pages.)

Peter’s Chair
By Ezra Jack Keats
Ages 3 to 7
It’s his old favorite chair, so he runs away with it. (Because, duh, the baby will take everything.)

101 Things to Do With Baby
By Jan Ormerod
Ages 4+
From testing the bath to helping dress the baby, there are lots of things to make a reluctant older sibling feel involved, not left out.

New School

Llama Llama Misses Mama
By Anna Dewdney
Ages 2 to 5
This classic expertly captures the up-and-down emotions of a toddler—Yes! Mama comes back!—making it easy for kids to connect.

Bob and Flo
By Rebecca Ashdown
Ages 4 to 7
Two penguins forge a bond on the first day over a pink lunch bucket. (Message: You’ll find a friend.)

Timothy Goes to School
By Rosemary Wells
Ages 2 to 5
Finding a good friend can take a little time. This is a good read for kids who may feel left out at first.

The Truth About Twinkie Pie
By Kat Yeh
Ages 8 to 12
A story about sisters who move from a trailer park in South Carolina to New York and have to adapt to a fancy new school, this perfectly captures what it’s like to be an outsider.

New Kid, New Scene: A Guide to Moving and Switching Schools
By Debbie Glasser and Emily Schenck
Ages 8+
Written by a psychologist and her college-age daughter, this is packed with tips and quizzes to help kids find their way.


When Dinosaurs Die
By Laurie Krasny Brown
Ages 4 to 8
A straightforward story that covers the basics—what “dead” means, for starters—through the lens of a dinosaur family.

Death Is Stupid
By Anastasia Higginbotham
Ages 4 to 8
Why pat answers (“She’s in a better place”) don’t always make sense—and how to really move on.

I Miss You
By Pat Thomas
Ages 4+
The question “What about you?” appears often, helping you gently assess how your kid really feels.

By Bryan Mellonie and Robert Ingpen
Ages 5+
This book soothingly explains life cycles for everything from birds to bunnies to people. The takeaway? Death is a part of life.

The Thing About Jellyfish
By Ali Benjamin
Ages 10+
Written from the perspective of a 12-year-old grappling with the drowning of a friend and finding reconciliation.

Tear Soup: A Recipe for Healing After Loss
By Pat Schwiebert and Chuck Deklyen
Ages 8+
“This is a parable about a woman making soup who weaves in the stages of grief as she cooks. It reminds kids that recovery is a process,” says Katherine Megna-Weber.


The Care & Keeping of You 1
By Valorie Lee Schaefer
Ages 8+
Part of the American Girl series, this helps girls on the cusp of puberty who might not be asking questions—yet. Topics range from bad breath to pimples to buying a bra.

Will Puberty Last My Whole Life?
By Julie Metzger and Robert Lehman
Ages 9 to 12
A unisex book with a buddy-buddy tone—it answers a lot of real-life questions from other tweens—that tackles issues with humor and accuracy.

This One Summer
By Mariko Tamaki and Jillian Tamaki
Ages 12 to 18
Need a break from hormone facts? Grab this: a graphic novel (i.e., comic book-style) about the emotional trickiness of being not yet grown-up.

The “What’s Happening to My Body?” Book for Boys
By Lynda Madaras and Area Madaras
Ages 12 to 15
All of the essentials (body hair, growth spurts, even a chapter on romantic feelings), plus boy-centric sections, like Penis Size: The Long and Short of It.


What’s the Big Secret?
By Laurie Krasny Brown
Ages 4+
How babies are made, clear and simple—without too much detail about the, well, actual sex. In other words, it’s age-appropriate.

It’s Perfectly Normal
By Robie H. Harris
Ages 10+
“This book has been popular for more than 20 years, and for good reason. It teaches kids the matter-of-fact basics about sex, puberty, birth control, and much more,” says Lynn Lobash.

Sex, Puberty, and All That Stuff
By Jacqui Bailey
Ages 11 to 16
A witty guide that gets straight to what most teens are thinking about, including ways to say no.


By Kathryn Otoshi
Ages 4+
Set up as a color and counting book (Red is a meanie), it emphasizes how one person can make a big difference in a group dynamic.

The Juice Box Bully
By Bob Sornson and Maria Dismondy
Ages 4+
Written by teachers—who clearly understand playground dynamics—the message here is that you’re not alone.

Simon’s Hook
By Karen Gedig Burnett
Ages 6+
A simple fishing analogy—Don’t bite at every “hook”—helps kids deal with teasing and tough situations.

My Secret Bully
By Trudy Ludwig
Ages 6 to 9
This story deals specifically with emotional bullying—exclusion, manipulation—in a group of girl friends. The main character takes power back with the help of her mother.

Stand Up for Yourself and Your Friends
By Patti Kelley Criswell
Ages 8+
“This is a concrete guide to understanding friendship dynamics, and it encourages girls to hold a mirror up to themselves and their friendships. It’s kind of like having a therapist in the room,” says Pauline Jordan.

Blue Cheese Breath and Stinky Feet
By Catherine Depino
Ages 9+
A short chapter book that shows how one picked-on kid makes a plan—with the help of his awesome parents!—to deal with a hurtful bully.

By Laurie Halse Anderson
Ages 12 to 18
An empowering young-adult novel (note: the plot deals with a rape in high school) about learning to speak up for yourself.


Was It the Chocolate Pudding?
By Sandra Levins
Ages 4+
No, splattering pudding everywhere didn’t make Mom move away.

It’s Not Your Fault, Koko Bear
By Vicki Lansky
Ages 3 to 7
Another one to reassure kids that they aren’t to blame—with tips for parents in the margins. “Young kids always gravitate toward this book because it has bold colors and it’s sort of funny,” says Molly Jardiniano.

Divorce Is the Worst
By Anastasia Higginbotham
Ages 4 to 8
Although children are often told, “It’s for the best,” it rarely feels like that. This frank book follows kids and parents dealing with everyday life (washing dishes, vacuuming) while feeling angry or sad.

Divorce: The Ultimate Teen Guide
By Kathlyn Gay
Ages 14 to 18
This book addresses both the practical logistics and the emotional effects of divorce, with plenty of vignettes and examples.


Do You Sing Twinkle?
By Sandra Levins
Ages 3+
This answers little-kid questions about not only new stepparents but also new siblings, too.

The Invisible String
By Patrice Karst
Ages 3+
For kids who go between homes, this sends the message that they can still feel connected to their parents regardless of whose house they’re in.

Bigger Than a Bread Box
By Laurel Snyder
Ages 8 to 12
A powerful novel about 12-year-old Rebecca, who moves with her mom to her grandmother’s house after her parents’ divorce. A magic bread box that grants wishes makes things better—but then more complicated.

The Sisterhood of the Traveling Pants
By Ann Brashares
Ages 12+
“Though mostly a story about the power of women and friendship, there’s a really relatable portrayal of one character’s parents’ divorce and her visiting her dad who is getting remarried. Her despondence is captured perfectly,” says Cora Collette Breuner.

Gender Identity and Sexual Orientation

10,000 Dresses
By Marcus Ewert
Ages 5 to 9

This is about a girl born in a boy’s body who dreams of dresses—bringing in the theme of being misunderstood, with a comforting message that it’s all going to be fine.

Elena’s Serenade
By Campbell Geeslin
Ages 3 to 7
A girl defies gender stereotyping by pursuing her dream of being a glassblower in Mexico.

By Alex Gino
Ages 8 to 12
A wonderful, important story that centers on a girl who was born in a boy’s body—she’s named George but knows she’s really Melissa.

More Happy Than Not
By Adam Silvera
Ages 13+
A boy from the Bronx grappling with his sexuality contacts a mysterious institute to try to erase his orientation. “It’s compelling, and it creates a space for conversation about social class, sexual identity, and memory,” says Kevin Hicks.

Aristotle and Dante Discover the Secrets of the Universe
By Benjamin Alire Saenz
Ages 12+
A coming-of-age story about two boys’ growing friendship (and, eventually, relationship), as well as coming to terms with family history.

Family Diversity

The Family Book
By Todd Parr
Ages 3 to 6
“It presents children with a whole portfolio of different kinds of families. It’s really wonderful for little kids starting school, who might encounter and wonder about families that look different from theirs,” says Eliza Byard.

And Tango Makes Three
By Justin Richardson
Ages 4 to 8
Focusing on two male penguins who adopt a baby penguin, this affirms that no matter what your family looks like, it’s legitimate.

Asha’s Mums
By Rosamund Elwin and Michele Paulse
Ages 9 to 12
Which name on the school permission slip is her mum? Well, it’s both. One little girl tackles questions about same-sex parents (making it easy for you to do the same with your kids).

Recommended by the Following:

  • Cora Collette Breuner, M.D., pediatrician and professor at Seattle Children’s Hospital.
  • Eliza Byard, executive director of GLSEN, a gay, lesbian, and straight education network based in New York City.
  • Kevin Hicks, PH.D., president and head of the Stevenson School, in Pebble Beach, California.
  • Kathryn Hoffses, PH.D., pediatric psychologist at the Nemours/Alfred I. duPont Hospital for Children, in Wilmington, Delaware.
  • Molly Jardiniano, senior program manager of child and parent education at the San Francisco Child Abuse Prevention Center.
  • Pauline Jordan, PH.D., clinical psychologist in Greenwich, Connecticut.
  • Ann Levine, assistant manager at Bank Street Book Store, in New York City.
  • Lynn Lobash, manager of reader services at the New York Public Library.
  • Katherine Megna-weber, children’s specialist at Books Inc., in San Francisco.
  • Taylor Nam, children’s specialist at Books Inc., in San Francisco.
  • Kelsey Parker, high school counselor at the Bay School of San Francisco and a psychotherapist in private practice.
  • Laurie Zelinger, PH.D., psychologist specializing in clinical/school psychology in Cedarhurst, New York.