Starting something new can be exciting, but for many kids, it can also be a bit scary. Whether it’s the first day of school, their first sleepover, or trying something they’ve never done before, those big feelings are real. If you’re a parent or teacher helping a child through one of these milestones, these books about first-time experiences offer the perfect mix of empathy, encouragement, and fun. They help children understand that it’s okay to feel nervous and that new things often lead to great adventures. These picture books are perfect for sparking meaningful conversations about bravery, change, and growing up.
1. First Day Critter Jitters by Jory John
All the animals are feeling a little nervous about their first day of school—the snake worries about holding pencils, the giraffe thinks the bus is too small, and others have their own concerns. This humorous and heartwarming book uses animal characters to highlight the universal feelings kids have before starting school. It’s a fun way to show that everyone gets jitters, and that things usually turn out just fine.
The playful illustrations and funny scenarios help kids laugh through their fears and realize they are not alone. By the end of the story, the critters discover that their teacher has first-day jitters too, making this a reassuring read for both students and adults.
2. Lena’s Shoes Are Nervous by Keith Calabrese
Lena is excited for her first day of school—but her shoes are not. In this sweet and imaginative story, Lena learns to listen to her nervous shoes and help them find courage. This clever metaphor makes it easier for children to talk about their own anxiety and find ways to face it.
Told with warmth and humor, the story gently introduces the idea of emotional regulation. The artwork captures Lena’s inner world with charm, making it a perfect choice for shy or hesitant little ones stepping into a classroom for the first time.
3. The Night Before the Tooth Fairy by Natasha Wing
Losing your first tooth is a big deal, and this fun rhyming story captures all the excitement (and a little nervousness) that comes with it. A young boy wiggles his tooth all day and wonders what the Tooth Fairy will bring. This book mixes humor and anticipation while giving kids a positive spin on growing up.
It’s part of the popular “Night Before” series, so the rhyming structure and pacing are familiar and easy to follow. The focus on bedtime routines and the magic of childhood milestones makes this a comforting pick for kids going through the same moment.
4. Amah Faraway by Margaret Chiu Greanias
Kylie has never met her grandmother, Amah, who lives across the ocean in Taiwan. When she visits for the very first time, everything feels strange—from the language to the food and customs. But as the days pass, Kylie and Amah find ways to connect, laugh, and build a bond that goes beyond words.
This story gently explores the experience of meeting distant family for the first time, especially when cultures and lifestyles are different. It’s perfect for children visiting relatives abroad or navigating bilingual, multicultural families. The mirrored text structure and soft illustrations add depth to this heartfelt journey of love and belonging.
5. No Pants! by Jacob Grant
Pablo is getting ready for his first party, and there’s just one problem—he refuses to wear pants. This hilarious and warm-hearted book explores the tug-of-war between independence and rules that kids often face. A playful and relatable look at the emotions tied to growing up and stepping into new social experiences.
Pablo’s negotiation skills and strong opinions make this story incredibly funny while still offering a clear emotional core. The parent-child relationship adds depth, and the ending is satisfying for both adults and little readers. It’s a great read-aloud that invites laughter and discussion.
6. How to Get Your Octopus to School by Becky Scharnhorst
Sending an octopus to school is no easy task. He hides in odd places, squirts ink when nervous, and needs lots of encouragement to face the day. This humorous story follows a determined caregiver trying every trick in the book to help her octopus get ready for his very first day of school.
While it’s full of silly situations and laugh-out-loud moments, the story cleverly mirrors the real emotions kids feel about starting school—resistance, nervousness, and the need for patience and love. The playful tone and colorful illustrations make this book a hit with reluctant readers and anxious little ones alike. It’s a perfect choice for easing school-related anxiety through humor and imagination.
Want a FREE children’s book?
Hey! I’m B.C. Stephan the one who put this free site together for fun.
I’m also a children’s book author and I’m trying to build a community of not just parents and teachers, but also people who just love to learn about our world and want to make a positive impact.
So I would love it if you joined the newsletter.
I’ll even bribe you with a free copy of my eBook The Best Worst Day Ever… 😉
