Walking Beside Bilbo: Insights on Friendship In The Hobbit for Middle School Readers

There are books that stay with me long after I’ve finished reading them, and The Hobbit is one of those. Every time I return to it—whether on my own or with my students—I discover something new. Among all, I am always struck by the way Tolkien portrays friendship lessons in The Hobbit with such depth and honesty: this story of dragons and dwarves, of hobbits and perilous roads, offers some of the most profound lessons on what it really means to walk alongside someone. Teaching middle schoolers, I see every day how important friendship is in their lives, how it shapes their identity and gives them courage. Reading Bilbo’s journey together becomes a way to talk not only about literature, but about life.

That friendship is a cornerstone of The Hobbit is perhaps not surprising: Tolkien himself experienced deep bonds rooted in shared interests but also in embracing differences. His close-knit circle of literary colleagues, the Inklings—including C.S. Lewis—demonstrated how friendships between diverse individuals can spark creativity, challenge ideas, and nurture growth. As Tom Shippey notes in J.R.R. Tolkien: Author of the Century (HarperCollins, 2000), the Inklings’ collaborations were formative in shaping Tolkien’s mythological imagination. I explore this in more detail in my article Introducing The Hobbit in Middle School: Unveiling Runes and Pub Lore, which suggests beginning the reading of the novel by reflecting on Tolkien’s own friendships. Sharing Tolkien’s experiences with the Inklings alongside the friendships in his novels helps students see that loyalty, courage, and mutual respect are not just literary themes—they are life lessons.

If you’d also like to see how friendship fits into the broader educational value of the novel, you can explore my article on the educational value of The Hobbit in middle school, where courage, curiosity, moral reasoning, and social growth are discussed alongside friendship.

Now, let’s dive into the key features of friendship in The Hobbit.

At the beginning of The Hobbit, Bilbo Baggins is far from the heroic figure he will become. He loves the comfort of his hobbit-hole, his quiet routines, and his orderly life. The thought of venturing into the unknown with a company of boisterous and opinionated dwarves is deeply unsettling. Yet, it is precisely this step beyond his comfort zone that sets the stage for profound friendships. His initial reluctance reflects a truth familiar to middle schoolers: venturing into the unknown can feel risky, especially when it involves trusting and collaborating with others.

Once Bilbo steps beyond the garden gate, everything begins to change. Friendship, Tolkien shows, often blossoms in surprising contexts. The dwarves are not companions he would have chosen willingly: they are brusque, boisterous, noisy — in short, not hobbit-like at all. Yet traveling together through danger and hardship forces Bilbo to confront his fears and assumptions, and in doing so, he discovers the meaning of true friendship. The story demonstrates that bonds are strengthened not by similarity or comfort, but by shared experiences, empathy, and willingness to face challenges together.

Verlyn Flieger, in Splintered Light: Logos and Language in Tolkien’s World (Oxford University Press, 2002), observes that Tolkien consistently uses companionship to catalyze personal growth, showing that adversity and diversity strengthen the heart of friendship.

Friendship in The Hobbit is not idealized—it is real, full of tension, mistakes, and reconciliation. Bilbo sometimes tries to protect his own reputation, as when he stretches the truth about his encounter with Gollum. He quarrels with Thorin, standing up to him in moments when pride threatens to tear the group apart. These tensions, however, do not weaken the bond — they deepen it. Friendship, after all, is not born of perfection but of perseverance, forgiveness, and the willingness to share the road even when it is difficult.

The turning point comes in the final chapters, as Thorin lies dying. Bilbo tells him: “I am glad to have shared in your perils, Thorin. It’s been more than any Baggins deserves.” As the Italian scholar Edoardo Rialti has noted, the key word is not perils but your. Bilbo is not thankful for the dangers themselves — they remain unpleasant, frightening, and uncomfortable. What makes the difference is the fact that they were Thorin’s dangers. In other words, Bilbo discovers that the value of the journey lies in the bond with his friend. “I would rather have wept with you than stayed home laughing alone,” Rialti explains.

Friendship in The Hobbit does more than provide companionship—it transforms who we become. By the end of the story, Bilbo returns to the Shire, aware that he has lost some of his former reputation among the other hobbits, who now regard him with curiosity or mild suspicion. Once, the approval of his neighbors, his routines, and his small comforts had defined him. After his adventure with the dwarves, those things matter less—not because he has abandoned them, but because he has grown into a fuller, truer version of himself.

The friendships Bilbo formed with Gandalf and the dwarves guided this transformation. Through shared risks, laughter, and mutual reliance, he discovered courage, empathy, and the willingness to act beyond self-interest. It is these bonds, rather than the adventures alone, that shape him into a more mature, self-aware individual.

This theme continues in The Lord of the Rings, where the unforgettable friendship between Frodo and Sam exemplifies the same truth Bilbo discovered: that what makes the perils bearable, even meaningful, is not the journey itself but the one who walks beside us.

When I think about teaching literature, this is what excites me most: the way stories can speak to the real questions of growing up. My students might not face dragons, but they do face uncertainty, loneliness, and the search for belonging. Reading The Hobbit together becomes an encounter not just with Bilbo’s story, but a mirror for their own experiences with friendship.

Bilbo’s journey shows that true friendship often grows in unexpected places and with people who are very different from ourselves. He learns to navigate disagreements, forgive mistakes, and offer support even when it is difficult—all lessons that resonate deeply with middle school readers. And if a book can help a young person see that friendship is worth the risk, worth the quarrels and the tears, then it’s a story worth telling—and retelling—for years to come.

Thanks for walking through these reflections with me — I’d love to hear how you’ve seen your own students connect with the theme of friendship in Tolkien’s works.

Warmly,

Chiara

If you’re looking for a way to explore The Hobbit with your middle school students in a structured and engaging way, I’ve created a complete teaching bundle that covers the novel from multiple angles. It includes activities for character analysis, theme exploration, creative writing, and final assessments—everything you need to guide students through Bilbo’s journey while encouraging them to reflect on the deeper meanings of the story.

You can find it here:

And for more creative classroom strategies, you can also check my posts on using crossword puzzles to enhance learning or a comprehensive guide to close read the novel, chapter by chapter.