This reading group guide for UNDERESTIMATED includes an introduction, discussion questions, and ideas for enhancing your book club. The suggested questions are intended to help your book club find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.

Introduction

“If you have a teenage girl in your life, you need to read this.” —Oprah Daily

In the vein of Reviving Ophelia and Untangled comes a fresh, unexpected, and empowering guide to better understanding teenage girls, revealing how their insights can create heartfelt connections and impactful change.

Written with warmth and humor, Underestimated is the first book to invite us into a teenage girl’s brain and heart, as told from the point of view of a beloved and trusted mentor. Chelsey Goodan is a highly sought after academic tutor who has worked with hundreds of girls from all different backgrounds, earning their trust, confidence, and friendship. They in turn have shared with her their innermost concerns, doubts, and what they wish they could communicate to their parents and the world at large.

With topics and language directly chosen by the girls, Chelsey reveals how the solutions to a girl’s well-being lie within her. She offers parents the exact words they can use to help her discover these solutions and demonstrates how adults can better support a teenage girl’s voice to create positive change.

Rather than dismissing teenage girls based on our own fears or treating them as problems that need to be solved, Chelsey encourages us as parents, and as a society, to help girls unleash their power and celebrate their intrinsic wisdom, creating more healing and connection for everyone. With inspiring ease, Underestimated shows us how to do this with accessible advice, entertaining narratives, and profound wisdom.

Topics & Questions for Discussion

FEAR—In her introduction, Chelsey writes that “The world fears teenage girls, and that fear is used to silence them . . . This fear seeps into our own insecurities, knowing that a teenage girl has the ability to rip us apart at any moment with her cutting, perceptive words” (xiii–xiv).

What stereotypes come to mind when you think of teenage girls? Do you believe these stereotypes are accurate? As you read, consider how we can look beyond inaccurate tropes and develop a more respectful, nuanced understanding of teenage girls.

FEELINGS—Recall a time when a teenage girl in your life was having an emotional moment. How did you respond? Did you acknowledge and hold space for her feelings? Chelsey observes “that people, including teenage girls, open up when you meet them exactly where they’re at, with no agenda” (7). With this in mind, how might you better support constructive emotional regulation for teenage girls (or anyone in your life)?

CHOICE—Chelsey believes that trusting teenage girls to make their own choices—whether right or wrong—leads to empowerment. She considers trust an act of L.O.V.E (Let Others Voluntarily Evolve) (19). Do you give this freedom to the teenage girls in your life? Do you receive it? Discuss how freedom of choice is tied to a teenage girl’s authentic sense of self and agency.

SEXUALITY—Do you feel uncomfortable talking about sex with your teenage girl? Why or why not? “It can be complicated,” Goodan acknowledges, “but please don’t underestimate a teenage girl’s ability to have a conversation about it. Growth and learning happen in an environment that’s filled with respect and curiosity, not shame and judgment” (40). If you haven’t already, how can you approach this subject with your teenage girl? If already broached, in what ways are you meeting her where she’s at and helping her feel understood?

PERFECTION—Chelsey encourages “embracing the gray zone” (58) because “expectations of perfection and binary thinking block exploration, innovation, and the overall learning process” (61). What role does perfection play in your teenage girl’s life? How can we embrace “the gray zone” and foster healthier understandings of self-compassion and worth?

COMPLIMENTS—Chelsey asserts that “as long as a compliment is grounded in sincerity, there is a never-ending abundance of love, care, and appreciation that people can both give and receive” (81). She calls people to “state your appreciation frequently and thoroughly, even if it seems obvious. Specifically compliment the values, actions, and character traits that help a person feel seen, really seen” (80).

Does the chapter on compliments counter or support your current approach to positive affirmation with teenage girls? Think of a recent compliment you’ve given, received, or thought but neglected to say aloud. Would you alter your approach to compliments after reading this chapter?

RADICAL HONESTY—In the chapter on radical honesty, many teenage girls express a feeling that adults are constantly lying to them in an attempt to shield them from complex issues. How does Chelsey argue that radical honesty holds the power to create trust with teenage girls? Do you think you have an honest relationship with the teenage girl in your life?

FRIENDS—Teenage girls are negatively stereotyped as dramatic—especially when they spend time with other teenage girls. However, when dissecting teenage girls’ relationships with their friends, Chelsey spins this stereotype into something positive. She views teenage “drama” as “passionate feelings mixed with honesty, vulnerability, and courage, giving her inner life a voice” (117). Chelsey notes that “we all have a deep need to feel loved as our authentic selves and that friends are a critical channel of that love, especially when we’re feeling our most imperfect and broken” (117).

What do you observe about your teenage girl’s friendships or remember about your friendships as a teenager? Is there anything you wish to emulate?

THE MEDIA—Chelsey writes that “the media offers a really easy access point to bring up topics with teenage girls that would feel forced otherwise” (127) and that “all types of media offer us a portal into crucial conversations” (132). Is there a shared piece of media between you and your teenage girl? If so, what types of conversations has it ignited? Has it helped your teenage girl explore her identity, value, or voice?

BEAUTY—It is an unfortunate reality that teenage girls hear “their moms, sisters, friends, teachers, and the women in their lives regularly comment negatively on their own bodies in front of them” (144). Teenage girls absorb beauty messages (both good and bad) from their surroundings. Regarding beauty and self-image, how can we be positive role models for the teenage girls in our life? Conversely, how can Gen Z’s evolving understanding of beauty and self-image dismantle harmful expectations from previous generations?

IDENTITY—How do you feel about the societal link between productivity and identity? Does the teenage girl in your life abide by this unspoken expectation? Chelsey challenges this logic and encourages everyone to “create space to explore your identity by doing things you’re bad at, without any obligation to productivity or achievement” (169). Consider ways you and your teenage girl may embrace this bold thinking (or how you may already be doing so).

SHAME—Reflect upon a period from your life when you felt shame. Did you share these feelings with anyone? If so, how did they respond? Chelsey states that it’s critical for people to share their pain with others and “equally critical to listen, because that space creates emotional safety” (178). Based on your own experiences and Chelsey’s insight, how do you handle this heavy topic with your teenage girl?

POWER—What comes to mind when you think of power? Chelsey points out that “teenage girls believe we need to redefine power, steering us away from the limiting concepts of power that are characterized by domination, oppression, ego, wealth, physical power, violence, and self-interest” (198). Does this new understanding of power challenge or support your previous definition? How can we help teenage girls step into their power?

LIBERATION—Underestimated ends with a discussion of making amends and holding space. Chelsey says, “If you have a teenage girl in your life who you would like to build love and trust with, I recommend making amends. Her heart and your heart will both expand in unexpected ways” (203). Is there a teenage girl with whom you wish to make amends? How can you better hold space for her feelings, choices, growth?

Enhance Your Book Club

Follow Chelsey’s suggestion from Chapter Six. Write out some compliments that your teenage self would have liked to hear (83). Make each compliment more than two sentences, and the more specific the better! To take this a step forward, write a compliment letter to the teenage girl in your life.

In Chapter Nine, Chelsey shares that “Longer amounts of quality time with friends, similar to a teenage girl slumber party, can be a source of connectedness that allows emotional walls to collapse and vulnerable connections to grow” (125). As Chelsey does, see if any of your friends want to join you for a slumber party. Take a tip from teenage girls, embrace the messiness of life, and let your guard down. Create a safe space for authentic conversations.

Share this book with the teenage girl in your life, whether that be reading the whole thing together or going over a specific chapter. Does she have any additional insight? Listen wholeheartedly and encourage deeper conversation. ​