How hard could it be to be a man? Six and a half months as Harry gave her the answer.

Before Harry

1. The book opens with “My whole life has been all about them—men.” What finally pushed Helie to try living as a man: anger, heartbreak, family pressure, or something else? Did you sympathize with her at the start?
2. Helie’s parents mail her headshot to strangers, and even her relatives across the North Korean border ask, “Is Hae-ri married?” How do culture and family shape what is expected of daughters versus sons in this book? What expectations shaped you?
3. In her author’s note, Helie explains that she is not a trans man and that her experiment had an end date she could walk away from. Why do you think she included this? How does the ability to leave change what she can and cannot learn?

Becoming Harry

4. The eleven-dollar haircut, the Ace bandages, the sock in the tighty-whities. Which moment of the transformation surprised or moved you most? What does it suggest about how much of gender is learned and performed?
5. Chris and Tom coach Harry: don’t smile so much, don’t move so much, no doe eyes. Which Guy Rule surprised you most? Which ones do you recognize in the men in your life, or in yourself?
6. Katie and Anna come to see Harry as “the ideal guy”: he cooks, listens, opens doors, and takes their advice. Why do you think Helie had never found those qualities in the men she dated? What does that say about what we ask of men?

Henry

7. After four hours of basketball, Home Depot, and sports TV, Helie knows almost nothing about Chris’s friends, yet Chris says, “Welcome to my world.” Is male friendship as shallow as it first appears to her? How does her view change over the course of the book?
8. At the wedding, the young men can talk about love only in the abstract, while the bridesmaids laugh about a man who shared too many feelings. Helie wonders whether women sometimes don’t let men be emotional. Do you agree?
9. At the Playboy Mansion, rejected by the Playmates, Helie suddenly realizes, “Now I’m Donald.” How does being on the other side of rejection change her understanding of dating, and of her own past behavior?
10. Jim, the cigarette salesman, feels he has no choice but to keep working at a job he doesn’t love, while his wife was able to quit hers. Helie admits she always assumed a husband would someday provide for her. What freedoms and burdens does each gender take for granted?

H

11. David Hyun sees through the disguise because of “the kind of tenderness only women possess.” What does their friendship give each of them? Why could David share things with H that he had never told another man, or even his wife?
12. David says that men “remain on the peripheral, gazing in, wishing to get in.” Think about David, his friend Leonard, and his old friends at the plaza. What does the book suggest about loneliness in older men?
13. Helie’s nightmares about her brother, David, become the mantra that keeps her going: “For David.” What does the book reveal about the pressures placed on sons, especially an only son in an immigrant family?
14. After the police stop, Helie collapses on the curb and realizes that pain doesn’t always look like sadness; sometimes it comes out as anger. How does this moment change the way she sees the men around her?

Coming Home

15. On the day she becomes Helie again, a Beverly Hills attorney waves off a car accident and calls her “darling.” What does the contrast between H and Helie in the same twenty-four hours reveal?
16. Helie writes, “Understanding men is not the same as excusing them,” and “Compassion is not permission.” How does she hold both truths, especially about Kevin? Do you find that balance convincing?
17. Early in the book, men on the street can’t name a single worst thing about being a man. After reading Macho Like Me, how would you answer that question? Has your answer about women changed too?
18. The book is dedicated to Helie’s son “as he becomes a man” and ends with a letter to her children. If you could hand the next generation a better rulebook, what would be in it?

Beyond The Book

• Watch the footage. Scan a few of the QR codes throughout the book and watch Harry in action. How does seeing the real footage change your experience of the story?
• Write your own rules. Have each person list five unspoken “Guy Rules” or “Girl Rules” they grew up with. Compare lists. Which rules are shared? Which still apply today?
• Notice for a day. For one day, pay attention to who touches whom, who apologizes, who takes up space, and who asks for help. Share what you noticed at your next meeting.
• Ask the men in your life. Ask a father, partner, brother, son, or friend Helie’s two questions: “What’s the best thing about being a man?” and “What’s the worst?” Listen closely to the answers, and to the pauses.