How a Fourteenth-Century Text Teaches Twenty-First-Century Skills: New Reasons for Teaching The Canterbury Tales in the Digital Age

How a Fourteenth-Century Text Teaches Twenty-First-Century Skills:

New Reasons for Teaching The Canterbury Tales in the Digital Age


Elaine Griffin

University School of Milwaukee

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The drumbeat from corporate America has become a din: companies need workers with skills, including communication skills, critical thinking skills, and character skills such as empathy and grit. Content, we’re told, matters much less than it once did now that information is so readily available on the world-wide web. But English teachers know that this perceived division between content and form – material and tools, substance and style, what we say and how we say it – represents a false dichotomy. True skill development comes from reading, interpreting, and learning to express and defend ideas involving complex texts. In other words, students must not only be able to speak and write in coherent and complete sentences, but must also have something of interest to say about a world that’s frequently not “relatable”; a world, in short, that’s both complex and seemingly foreign.

Cue Chaucer’s Canterbury Tales, which initially can seem about as foreign and complex a text as a high-school student is likely to encounter. Written in an older form of English – about a world and place that can strike the modern reader as belonging on an alien planet – it’s much less “relatable” than, for example, the contemporary Young Adult fiction that English teachers are increasingly likely to assign in an effort to reach their students.

For all that, my modest proposal in this essay is that Chaucer’s motley crew of pilgrims can be as compelling to twenty-first-century students as any text written in this century – while also teaching valuable, empowering lessons about empathy and diversity: how to communicate and how to judge character; how to live in a world of alternative pluralisms; and how, ultimately, to equip students with exactly those sorts of skills that they’ll need to survive and flourish in an increasingly fractured world. 


The Empathy Gap

In Reclaiming Conversation: The Power of Talk in a Digital Age, Sherry Turkle notes that there has been a forty percent decline in the markers for empathy among college students during the past two decades, with most of it taking place within the past ten years.[1] Although Turkle holds an endowed chair as the MIT Professor of Social Studies of Science and Technology, she indicts technology in explaining this “empathy gap.”[2]   

Longtime English teachers need not have read Turkle’s book to know exactly what she’s talking about. Having taught English for the same twenty-year period covered by the empathy study Turkle describes, I’m living with the fallout of students who have disappeared into their electronic devices, rendering them increasingly incapable of engaging texts in what novelist Richard Powers once memorably described as “the shared solitude of reading” or of engaging each other in organically grown, face-to-face conversation. Writing short blasts of texts rather than sustained thoughts and engaging through their devices rather than in person, students do not have enough opportunities to practice empathy. It is simply not being cultivated in the way that it would be if students were fully immersed for extended periods of time in others’ competing stories, whether through the page or through live conversation.

We can narrow this empathy gap by reclaiming our classrooms as device-free zones, while promoting the kind of conversation that requires deep listening and self-reflection – skills that are necessary for full participation in the sort of robust and respectful exchange and debate characteristic of free societies. As teachers of literature, we can model rich, in-person conversations that help students practice how to express themselves, empathize with perspectives very different from their own, and experience what it means to make meaning within a community of learners. Turkle cites evidence “that literary fiction significantly improves empathetic capacity, as measured by the ability to infer emotional states from people’s facial expressions. The English teachers were right, literally. First one identifies with the characters in a complex novel and then the effect generalizes.”[3]


Making Pilgrimage with Chaucer

While it may have been written long ago and far away, The Canterbury Tales is ideally suited to foster empathy because it offers no comforting and controlling narrator who tells the reader how and what to think. Instead, reading it demands active engagement and interpretation, both of the tales and of their tellers. And its fractured form and competing views – presented in a world shaken by the Black Death, famine, a crumbling feudal order, and the rise of the cities – offer a more accurately reflective mirror, however distant, of our own twenty-first-century world, one also marked by complex problems such as global warming, growing disparities between rich and poor, resource scarcity, a worldwide refugee crisis, and an erosion of rituals and traditions perceived as inadequate or even irrelevant to the challenges of modern life. The Canterbury Tales doesn’t provide answers; instead, it teaches students about the nature of inquiry. It poses questions, suited to a world – be it the fourteenth-century one in which Chaucer wrote or the one in which we live – in which answers regarding how to live in the world and how to know one’s proper place in the world seem increasingly hard to come by.   

No wonder we find the pilgrims presented in the General Prologue so puzzling. They’re shot through with contradictions; their titles and style of dress often challenge how they speak about themselves and what they profess to value; and many of them do not conform to the religious, gender, and cultural norms of medieval society. And because these characters refuse easy readings, students must put pressure on the language and scrutinize the evidence before determining each pilgrim’s values and motivations. Yes, students will struggle with this text as they work through misreadings and mistakes. But the map of their misreadings will, however paradoxically, better prepare them to navigate the similarly disjointed world in which they themselves live.

Take, for example, Chaucer’s portrait of the Prioress in the General Prologue. That portrait contains the language both of piety and of the more secular French romances. The Prioress enthusiastically sings her church hymns: “Ful weel she soong the service dyvyne” (I 122). Yet, just two lines later we read, “And Frenssh she spak ful faire and festisly, / After the scole of Stratford atte Bowe” (I 124-125). On the one hand, it is proper that the Prioress perform her office; on the other hand, given that she spoke French “faire and fetishly” or in an elegant and refined manner, the line suggests that the school being referenced here was expensive and exclusive rather than poor and pious.

Further, the Prioress takes great pride in her dainty eating habits: “She leet no morsel from hir lippes falle, / Ne wette hir fyngres in hir sauce depe; / Wel koude she carie a morsel and well kepe / That no drope ne fille upon hire brest” (I 128-131). In her explanatory note on this passage in The Riverside Chaucer, Florence H. Ridley points out that the Prioress’s eating habits mirror those mentioned in Ovid’s Ars amatoria (Art of Love), in a section of the poem “advising a young woman how to attract men,” but also acknowledges that nuns might have eaten carefully because of a responsibility to take good care of their religious garments. In the end, Ridley concludes that “[n]othing the Prioress consumes is explicitly forbidden by her rule, though the care with which her eating and drinking are described suggests improper concern with food and drink, as well as with manners.”[4]

Other lines in the Prioress’s General Prologue portrait might similarly strike a reader as wildly inappropriate given her religious role. We learn, for example, that while “She wolde wepe” (I 144) if she saw a mouse caught in a trap, that she fed her own dogs “rosted flessh” (I 147), and that rather than carry a rosary, she wears beads with a “brooch of gold” (I 160), which seems to testify to an interest in courtly love because it is stamped with the words “Amor vincit omnia” (Love conquers all; I 162). But even here, the Riverside gloss questions our assumptions, informing readers that “the phrase could apply to either divine or earthly love” (8). Note, too, that Chaucer deploys the word semely three times in this portrait,[5] hinting that perhaps the Prioress “seems” rather than “is” an authentic woman of the cloth. The only conclusion one can safely draw is that there is a level of irresolvable ambiguity in many of the words and phrases describing the Prioress. Because the Prioress resists being pigeonholed, we must understand her and empathize with her as an individual. We are prompted to see her both as a nun and as a woman, as someone who made a public vow to God but who also feels drawn to romantic expressions of the heart. In her we see wealth and worldliness where we might expect to see poverty and simplicity. The Prioress challenges our assumption that people of the cloth are immune to sexual desires, worldly cares, and even sin.

Another religious figure, the Pardoner, also cannot be classified, but in his case the lack of classification involves his gender identity: “No berd hadde he, ne nevere sholde have; / As smothe it was as it were late shave. / I trowe he were a geldyng or a mare” (I 689-91). Here students stop and ask for more clarity. Is the Pardoner a eunuch? Is he gay? We only know for sure that the Pardoner is a gender-fluid character who sells fake relics. Moreover, students also encounter a religious figure like the Parson, which forces them to draw a contrast between his ideal religious portrait and the Pardoner and Prioress’s comparatively worldly ones. Finally, students must wrestle with the fact that all three of these figures represent aspects of the religious world of the Middle Ages.


True Grit and The Canterbury Tales

Confronted with the unfamiliarity of Middle English and slippery characters who defy partial characterizations, students confronting The Canterbury Tales learn to heed my warning: “At first it’s going to be really hard.” That is all the more reason to have them grapple with a text like The Canterbury Tales; real learning happens when learning gets difficult. These are the times when students must [exercise the character skills required to] stretch their cognitive skills, when they must manifest the patience and “stick-to-it-ness” required to slow down, read aloud, and ask questions.

My thinking here reflects that of Paul Tough’s, in How Children Succeed: Grit, Curiosity, and the Hidden Power of Character.[6] Tough contends that possession of the character skills required to navigate through uncertainty or to recover from failure matter more in the long run than IQ in determining a student’s success in high school, college, or the real world. He cites the research of Angela Duckworth: when this “guru of self-control and grit at the University of Pennsylvania analyzed GPA and standardized-test scores among middle-school and high-school students, she found that standardized-test scores were predicted by scores on pure IQ tests and that GPA was predicted by scores on tests of self-control.”[7] In other words, Tough continues, “whether or not a student is able to graduate from a decent American college doesn’t necessarily have all that much to do with how smart he or she is. It has to do, instead, with that same list of character strengths that produce high GPA’s in middle school and high school.”[8]

As Tough argues, skills such as perseverance, conscientiousness, and optimism can be developed in young people: “the character strengths that matter so much to young people’s success are not innate; they don’t appear in us magically, as a result of good luck or good genes. And they are not simply a choice. They are rooted in brain chemistry, and they are molded, in measureable and predictable ways, by the environment in which children grow up.”[9] To develop qualities that stretch their problem-solving abilities, we need to challenge students with texts that promote uncertainly and ask them to persevere as they formulate their own conclusions.

I would like to illustrate this point with a few examples from my teaching of The Canterbury Tales. When students read the Franklin’s Tale in my AP English class, I pose the following question: “Among the three main characters, who is the most generous?” Inevitably, the students disagree, often citing compelling evidence for why their particular choice of character – Dorigen, Aurelius, or Arveragus (somehow, they never mention the Orléans clerk) – acted the most unselfishly. Each character has his or her own truth and way of seeing the world, and initially students connect with one of those perspectives. But through conversation and a close examination of textual evidence, they gradually come to see the possibility of multiple and competing perspectives, each one valid.

I use a similarly challenging exercise in empathy when I teach the Manciple’s Tale. I ask students to write on the board the moral of the story from the human perspective, and then to discuss and defend the moral they have written. After that, I ask them to write the moral of the story from the crow’s point of view. The morals they write are vastly different, depending upon which perspective the students adopt. Students aren’t used to adopting an animal’s point of view – no more than any of us is particularly adept these days at seeing the world through a lens other than our own. But both morals in this tale – predicated upon very different truths, as experienced by a cuckolded man and a caged bird, respectively – are valid.

In my experience, the most effective empathy exam among Chaucer’s tales comes through one of the most memorable and compelling of his characters, the woman who holds the stage in relating the Wife of Bath’s Tale. When I ask students to answer the question that the knight must answer in the tale – “What do women want?” – the answers are as varied as the number of women in my classroom. It’s not even clear to my students that this is a real question, as distinct from a riddle – a conundrum which, in turn, raises questions all its own, as timely today as they were when posed in this text more than half a millennia ago.

Not only do I challenge my students to take a fuller and more empathetic view of the characters in the tales being told, I also push them to focus on why the pilgrims telling these tales are unfolding the particular stories they share. Yes, we acknowledge, of course the characters aspire to tell “Tales of best sentence and moost solaas” (I 798) in order to win a supper at the other pilgrims’ expense. But they’re also driven by their own feelings and anxieties, which both shape, and in some cases, potentially mar the quality of the stories they tell.

The Miller decides to tell a raucous fabliau because he needs a break from the long and serious tale just told by the Knight. The Reeve, a carpenter, tells a tale about a duped miller because he dislikes the portrait of the cuckolded carpenter in the Miller’s Tale. The Wife of Bath is motivated to tell a story that showcases the power of an aging woman, promoting her own status among the pilgrims. In her tale, a knight, the most powerful person on the pilgrimage, is subject to the wishes of an old hag and placed in a fairy world he can neither control nor predict.

In other words, the tales don’t just serve as entertaining stories, but also serve the characters’ wishes to compete with their peers on the pilgrimage. And by learning through active listening to genuinely hear the tellers’ voices in the tales, students cultivate their empathy skills. When asked why a teller tells his or her particular tale, students often can’t initially draw solid conclusions. But reading the tales aloud and then discussing them with their peers does promote some understanding, while strengthening students’ abilities to both hear and engage others’ points of view. After learning about each tale and its creator, students start to gain an appreciation for the fact that the tales were collectively the invention of Chaucer and ultimately represent his world view. This additional layer adds yet another lens through which students come to see the medieval world.


Reading Chaucer and Embracing Diversity

Written in Middle English and a foundational text in what is still a largely white and male literary canon, The Canterbury Tales is nevertheless vitally important today because it promotes goals at the core of most diversity initiatives: tolerance, respect for difference, and the empowering knowledge that competing perspectives – espoused by dominant members of a culture such as knights and clerics as well as outsiders like outspoken widows – are equally valid. The Canterbury Tales also offers students from both wealthy and disadvantaged backgrounds something they all need: an opportunity to build grit and resilience.

Tough reports that teachers at Riverdale Country School, a co-educational independent day school in New York, “have talked a lot about affluence and its potentially detrimental effect on students’ character development.”[10] Many affluent parents, he notes, “while pushing their children to excel, inadvertently shield them from exactly the kind of experience that can lead to character growth.”[11] Affluent students often aren’t required to read challenging texts or write difficult papers alone: their parents help them, hire tutors, contact the teacher to ask for an extension, or simply complain when learning gets difficult. Tough calls this “a central paradox of contemporary parenting.”[12] Parents want to protect their children; that impulse isn’t intrinsically wrong. But “what kids need more than anything is a little hardship: some challenge, some deprivation that they can overcome, even if just to prove to themselves that they can.”[13] Struggling with Chaucer’s antiquated language, contradictory character portraits, and ambiguous moral lessons provides students with the sort of uncomfortable struggles through which real learning takes place.

But this kind of struggle isn’t good only for affluent students from the dominant culture. In her book Culturally Responsive Teaching and the Brain, Zaretta Hammond argues that culturally and linguistically diverse students are often at a disadvantage because they, like their more advantaged peers, haven’t developed the grit necessary when learning gets difficult.[14] Lacking the problem-solving skills that independent learners possess, these students tune out or give up when facing classroom challenges. Hammond emphasizes that these students, whom she calls “dependent learners,” need activities that provide them with time to process and practice hard concepts.

When Hammond was teaching at a community college in Washington State, many of her students were not used to being asked to analyze difficult texts: “They didn’t have tools or strategies. Most had been allowed to write about their opinions as if they were facts and pass it off as argumentation.”[15] One strategy she recommends to help students process difficult material is called Talk to Learn. This approach allots dependent learners time to think aloud as they grapple with complex ideas. In Hammond’s experience, “This kind of talk gives us the opportunity to organize our thinking into coherent utterances, hear how our thinking sounds out loud, listen to how others respond, and often, hear others add to or expand on our thinking.”[16]  An additional benefit is that “[t]hrough informal and formal conversations with other community members, students also acquire the ‘mental tools’ for processing information.”[17]

The point is that cultivating rich conversations about The Canterbury Tales helps all students develop the cognitive and character skills that support their academic learning and foster the development of their social and emotional skills. Some teachers make the mistake of believing that teaching multicultural texts is a panacea that will magically close the achievement gap. But we must remember that “[a]s important as including multicultural content is to making learning relevant, it alone doesn’t increase brainpower.”[18] It’s been my experience that helping students of all backgrounds write and talk about The Canterbury Tales provides them with the level of challenge required to give them real practice processing difficult language and ideas, thus increasing their cognitive development and helping to close the achievement gap. For example, the Wife of Bath is an ideal character to examine when teaching a lesson on characterization because she defies students’ expectations. I ask students to read her Prologue with the following question in mind: What makes a good marriage and a good wife, according to the Wife of Bath? They come to the text thinking it will confirm their stereotypes about sound marriages and marriage partners only to find that the wife undermines their preconceived ideas on both counts. To develop an accurate reading of her, students must rely on their close reading of the text rather than on their opinions about marriage. Only through careful reading do they see that the Wife of Bath values cleverness more than fidelity and her own power more than her past husbands’ authority. In this way, students learn that while characters are certainly shaped by their social class, religious affiliation, and gender, they are not defined by them. The Wife of Bath evades all such simplistic interpretations.  


Conclusion: A Text for All Seasons

In 2018, a canonical text like The Canterbury Tales may seem as distant, foreign, and, yes, even unappealing a choice as a teacher could make for a modern student. But past is often prologue; like Shakespeare, Chaucer is a writer both of and ahead of his time, beckoning us from a future that we’ve not yet reached. Teeming with a variety of voices and perspectives baked into an intrinsically dialogic text, The Canterbury Tales drives home that there is no monopoly on truth and no answer that is inherently and always right. As Mikhail Bakhtin made clear long ago in addressing the dialogic imagination, “language is not a neutral medium that passes freely and easily into the private property of the speaker’s intentions; it is populated – overpopulated – with the intentions of others.”[19][20] Chaucer’s book thus offers us a world – one that very much resembles our own, in which competing perspectives and stories vie for attention and power.

Destabilizing? Sure. Hard? You bet. But also hopeful and empowering? Absolutely. Even as they bicker – and even as they unwittingly expose their own foibles and internal contradictions – the pilgrims continue to wend their way together toward Canterbury, telling tales bound together much as they are, in a single capacious text making room for alternative pluralisms. High and low, lay and religious, young and old and stretched out along a gender spectrum, they embody the diversity that we espouse, while making clear through the lives they live and the stories they tell that there is never going to be a single answer. All the more reason for all of us to engage each other in conversation much as those pilgrims do, telling our own stories through those we read, as we learn to better interpret the world we’ve inherited so that we might journey toward the one we’re making together.



[1] Sherry Turkle, Reclaiming Conversation: The Power of Talk in a Digital Age (New York: Penguin, 2015), 21. Print.

[2] Ibid., 4.

[3] Ibid., 69.

[4] Geoffrey Chaucer, The Canterbury Tales Complete. Ed. Larry D. Benson (Boston: Houghton Mifflin, 2000) General Prologue, 340 and note to ll. 127-36.

[5] The General Prologue, I:123, 136, 151. Print.

[6] Paul Tough, How Children Succeed: Grit, Curiosity, and the Hidden Power of Characte,

(Boston: Houghton Mifflin, 2012). Print.

[7] Ibid., 153.

[8] Ibid.

[9] Ibid., 196.

[10] Ibid., 84.

[11] Ibid.

[12] Ibid.

[13] Ibid.

[14] Zaretta Hammond, Culturally Responsive Teaching and The Brain: Promoting Authentic Engagement and Rigor Among Culturally and Linguistically Diverse Students (Thousand Oaks, CA: Corwin, 2015).

[15] Ibid., 123.

[16] Ibid., 134.

[17] Ibid., 133.

[18]  Ibid., 123


Works Cited

Bakhtin, Mikhail. The Dialogic Imagination: Four Essays. University of Texas Press, 1994.

Chaucer, Geoffrey. The Canterbury Tales Complete. Ed. Larry D. Benson. Boston: Houghton Mifflin, 2000. Print.

Hammond, Zaretta. Culturally Responsive Teaching and The Brain: Promoting Authentic Engagement and Rigor Among Culturally and Linguistically Diverse Students. Thousand Oaks, CA: Corwin, 2015. Print.

Tough, Paul. How Children Succeed: Grit, Curiosity, and the Hidden Power of Character. Boston: Houghton Mifflin, 2012. Print.

Turkle, Sherry. Reclaiming Conversation: The Power of Talk in a Digital Age. New York: Penguin, 2015. Print.