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Penny Draws a First Crush
by Shepard, Sara
Penny is the kind of character who feels like a real friend, capturing the specific, messy anxiety of middle school with a sense of humor that makes even the most awkward moments feel manageable. In this installment, she is navigating the dizzying, often confusing territory of her first real crush. The book leans heavily into the diary format, using doodles and candid internal monologues to map out the small social victories and crushing defeats that define her days. It is a lighthearted but surprisingly introspective read that treats pre-teen feelings with genuine respect rather than condescension. If you enjoy stories that balance authentic growing pains with a warm, funny voice, you will find a lot to love here. It is perfect for readers who appreciate the intersection of creative self-expression and the universal struggle to just be yourself.
10 Books similar to 'Penny Draws a First Crush'
Since you enjoyed the diary-style format and the relatable social navigation in Penny Draws a First Crush, we have selected ten books that capture that same middle school spirit. Whether you are looking for more illustrated humor like Dork Diaries and Diary of a Wimpy Kid, or a deeper exploration of friendship dynamics found in Real Friends and Click, these picks focus on the awkward, heartwarming, and often hilarious realities of growing up. Each story mirrors Penny's journey through self-discovery and the pressure to fit in while staying true to your own unique voice.
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Much like Penny, Nikki Maxwell navigates the treacherous waters of middle school crushes and social dynamics through a highly personal, illustrated diary format. Fans of Shepard's relatable and humorous tone will find a similar spirit in Nikki's candid observations about friendship and fitting in.
by Jeff Kinney
This quintessential middle-grade diary series shares the same accessible, illustrated style and focus on the awkward, often hilarious realities of growing up. Readers who enjoy Penny's internal monologues about her daily life will appreciate the dry wit and situational comedy found here.
This book captures the intense anxiety and social pressures of middle school, mirroring Penny's own struggles with navigating new environments and friendships. It balances humor with a genuine look at the emotional challenges pre-teens face.
by Shannon Hale
This graphic memoir explores the complexities of childhood friendships and the anxiety of feeling like an outsider, themes that resonate deeply with Penny's experiences. It offers a poignant, honest look at the social hierarchies of elementary and middle school.
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Fans of the diary-style narrative will enjoy this fast-paced and funny series that focuses on the trials of middle school survival. It shares the same 'fish out of water' energy that defines Penny's attempts to navigate her first crush and school life.
This graphic novel beautifully captures the social ecosystem of middle school, focusing on the misunderstandings and growth that occur when navigating new relationships. The tone is sweet and relatable, making it a perfect follow-up for readers who enjoy Penny's journey.
by Kayla Miller
Olive is a relatable protagonist trying to find her place within her friend group, a struggle that Penny fans will immediately recognize. The story focuses on the social nuances of middle school and the importance of being true to oneself.
This book uses a dual-perspective, illustrated format to explore the lives of two very different girls, touching on themes of shyness, crushes, and self-acceptance. It mirrors the emotional vulnerability found in Penny's diary entries.
by Jerry Craft
Jordan Banks navigates the challenges of fitting in at a new school while balancing his artistic passions, much like Penny's own creative outlets. It is a thoughtful and funny exploration of the social dynamics that define the middle school experience.
While slightly more mature in its reflection, this classic novel explores the intense feelings of first love and the pressure to conform, which are central themes in Penny's life. It provides a more philosophical look at the 'crush' experience.
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As an Amazon Associate, we earn from qualifying purchases.
As an Amazon Associate, we earn from qualifying purchases.