WEEK 19: Can You Love Your Country in a Divided Age?

This week, we open by reacting to this year’s Super Bowl commercials — what they reveal about American culture, corporate messaging, and the stories companies think will resonate with young people today.

From there, we turn to the Supreme Court’s gay marriage decision and its long-term cultural and legal consequences. We discuss how marriage has been redefined in American law, what that shift has meant for religious liberty, family formation, and public morality, and why these questions remain unresolved a decade later.

The centerpiece of the episode is a deeper conversation about patriotism, cynicism, and national identity. In light of recent comments from U.S. Olympic athletes and growing distrust toward political institutions, we ask: Can you love your country while being deeply critical of its leaders? Is modern “activist patriotism” compatible with gratitude and loyalty? And has Gen Z been taught to see America primarily as something to apologize for rather than steward?

We wrestle with whether healthy love of country requires honesty about injustice without collapsing into permanent resentment — and how Christian ethics shape our understanding of citizenship, responsibility, and public life.

We close with Girl Problems, responding to listener questions about modern dating pressures, political compatibility in relationships, and realistic timelines for engagement and marriage in a high-pressure professional environment.

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

07:48 Rating Super Bowl Commercials

24:42 The Gay Marriage Supreme Court Case

36:41 Can You Love Your Country?

54:10 Girl Problems: Hoeflation

1:01:09 Girl Problems: Do Politics Matter in Dating?

1:04:40 Girl Problems: Ideal Timeline for Dating/Engagement

WEEK 18: In this episode, we sit by the frozen-over Charles River and work through listener feedback, campus reactions to the show, and what it’s been like navigating growing recognition — both positive and negative — at Harvard Law.

We respond to a thoughtful listener challenge on free will, causality, and moral responsibility, exploring whether human choice can be meaningful in a world shaped by causes — and how Christianity understands freedom, agency, and accountability.

From there, we turn to one of the most sensitive and important topics we’ve tackled so far: birth control, emergency contraception, and IVF. Beginning from a conception-based moral framework, we walk through the biological and ethical questions behind fertilization, implantation, and different contraceptive methods. We lay out clear categories, practical decision rules, and how Christians can think carefully and consistently about conscience, medical mechanisms, and moral responsibility — without outsourcing moral reasoning to labels or institutions.

The second half of the episode shifts to foreign policy and civilizational questions, as we ask whether Europe has reached an inflection point. Using current tensions over Greenland, NATO, and American leadership as a starting point, we zoom out to examine Europe’s Christian roots, its process of secularization, demographic decline, migration pressures, and political backlash. We discuss whether a civilization can preserve moral ideals after cutting itself off from the spiritual foundations that produced them — the “flower and stem” problem.

We close by offering a realistic path forward for Europe and the West, balancing strategic realism, cultural sobriety, and spiritual clarity — and what Americans should learn before repeating the same mistakes.

Finally, in Girl Problems, we respond to listener questions about new faith, past relationships, dating intentionally in law school, and navigating long-distance relationships with wisdom and honesty.

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

02:37 Quick Feedback

04:03 Immigration Update

05:13 Meta Narrative on the Podcast

08:43 Free Will vs. Predestination

14:34 Should This Engineer Go to Law School?

17:38 Birth Control

42:54 European-American Relations and the Future of Europe

1:03:46 A Very Personal Girl Problems Segment

WEEK 17: Welcome to Will’s home. In the snow. This week, we open with a long overdue feedback segment — responding to some of the strongest reactions we’ve gotten all season (including the Israel episodes, Larissa Part 1 & 2, and the Gen Z/Ozempic debate). We read comments ranging from thoughtful critiques to outright hostile takes, and we talk about what it means to have real disagreement online without turning into either cowards or flamethrowers.

Then we hit an appetizer we keep getting asked: Does Harvard have a serious Christian community? And does it help or hurt to be a conservative Christian applying to — or surviving at — Harvard Law?

The main course is the episode title: we rate Year One of the Trump administration across five categories, from F to A+:

- National Security / Foreign Policy (Rubio at State, NATO pressure, China tariffs, Ukraine strategy, Israel/Iran posture, global institutions)

- Immigration (border emergency posture, asylum policy changes, interior enforcement, detention levels, and the moral tradeoffs)

- Culture War (DEI rollback, Title IX/sex-and-gender policy, religion/parental rights, Department of Education and foreign aid, Planned Parenthood funding fights)

- Economy (GDP swings, inflation, wages, jobs, debt, youth unemployment, and whether tariffs are strategy or self-harm)

- Moral + Effective Leadership (executive power, staffing, DOJ posture, special counsel policy, and the administration’s aggressive use of pardons)

We try to do what most commentary won’t: give the best version of the case for each move and the most serious objections — then land on a grade.

And because we can’t help ourselves, we close with Girl Problems:

- Dating across Christian denominations

- Do you date one person at a time?

- Promise rings: sweet, cringe, or situational?

- How do you plan to raise kids in this modern era?

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

2:54 Reviewing ALL the Feedback

13:17 Being Christian and Conservative at Harvard Law

19:45 Grading Trump’s First Year Back

57:51 Girl Problems

WEEK 15 (PART TWO): We’re back at Harvard Law with Larissa Truchan for part two of our conversation, and the discussion gets even sharper.

We start by sketching out our ideal third parties, debating what’s missing from the current political landscape, and whether America is locked into a permanent two-party system. From there, we make early predictions for the 2028 election, breaking down who we think will win the Democratic and Republican primaries — and why.

The second half of the episode turns to Girl Problems, where we tackle listener questions and cultural flashpoints: Can guys tell girls what to wear? Should couples prioritize having kids? Are stereotypes about liberal women and conservative men fair or completely off base? And who should pay on the first date?

We close by each offering a piece of hard advice to our own side and to the other, even if it’s uncomfortable. Give it a listen!

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

00:40 Our Ideal Third Parties

12:45 Who Will Win in 2028?

34:05 Girl Problems: Stereotypes about Liberal Guys

42:11: Girl Problems: Not Having Kids

50:25 Girl Problems: Stereotypes about Conservative Guys

54:47 Girl Problems: Are Will and Mason Feminists?

58:40 Girl Problems: Modesty!

1:05:04 Our Parting Advice for a Better Political Future

WEEK 15 (Part 1): In front of the Harvard Law library, we sit down with Larissa Truchan — a Harvard Law student and viral leftist political influencer — for the first part of a two-part conversation across ideology, faith, morality, and power.

We start by getting to know Larissa: her background, family, and path to Harvard Law, as well as how she built a large political following online — including what it’s like to create content that doesn’t always land the way you expect. We also dig into the distinction between leftism and liberalism, and how Larissa understands that divide.

From there, we talk faith. Larissa reflects on growing up Catholic, attending Boston College, and how she thinks about religion, morality, and justice today. We discuss how faith does — and doesn’t — shape political commitments, especially in elite academic spaces like Harvard.

The heart of the episode centers on Jonathan Haidt’s moral foundations theory, as we walk through a series of provocative moral hypotheticals designed to test whether our disagreements are about right and wrong or simply about taste and culture. These scenarios reveal sharp contrasts and many similarities in how leftists and conservatives reason about morality, norms, and meaning.

We close by turning to foreign policy and power: whether the United States should act as “the world’s policeman,” and how to think about American intervention abroad, including the recent U.S. operation in Venezuela and what it reveals about sovereignty, justice, and global order.

This is Part 1 of a longer conversation. Part 2 continues with deeper disagreement, sharper exchanges, and higher stakes.

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

01:30 Getting to Know Larissa

02:57 Why She Came on the Show

09:34 Distinguishing Leftism from Liberalism

11:38 Faith, Christianity, and Morality

24:13 How Larissa Got into the Social Media World

27:05 Infighting on the Left and Right

29:37 Differences Between the Left and Right at Harvard

31:19 Moral Tastes Hypotheticals

53:27 American Hegemony: Good or Bad?

1:33:27 Next Week!

WEEK 14: Returning from a trip to Israel, we sit down with Shanee Markovitz Kay — an Israeli American and fellow Harvard Law student — for a deeply personal conversation about Israel, identity, and what it has meant to be Jewish at Harvard Law in the aftermath of October 7.We begin by getting to know Shanee — her background, her path to Harvard Law, and her (as well as our) involvement with the Harvard Law Alliance for Israel — before stepping back to talk about the wide spectrum of Jewish religious and cultural practice, both in Israel and in the United States.At the center of the episode is October 7th. Shanee shares her personal experience, how it affected her family, her community, and her sense of safety, and what it was like to process those events while being a student at Harvard. We talk candidly about the response to October 7th on campus: the protests, silence, hostility, support, and the emotional and social cost of navigating elite academic spaces during a moment of global attention and polarization.We then turn to Israel’s response — the moral, political, and strategic questions it raised — and Shanee reflects on what she believes the way forward looks like, both for Israel and for those trying to engage honestly across deep disagreement.After Shanee leaves, we stay on to offer immediate reactions to the conversation, reflect on our own recent trip to Israel, and zoom out to discuss the history of the modern Israeli state, U.S.–Israel relations, and the broader geopolitical stakes often missing from campus discourse.We close, as always, with Girl Problems: Israel edition.This episode is personal, serious, and at times difficult — but it’s an honest attempt to listen, understand, and speak clearly about Israel, identity, and truth in a moment when those things feel especially contested.00:00 Introduction01:43 Getting to Know Shanee09:20 Harvard Law Alliance for Israel12:37 The Spectrum of Jewish Practice15:42 How Shanee Ended Up at Harvard Law20:36 October 7th35:08 The Response to October 7th at Harvard51:49 Israel’s Response to October 7th55:24 The Way Forward (Shanee)1:00:13 Post-Interview Immediate Reactions1:12:53 Our Trip to Israel1:41:00 The History of Israel1:46:19 America–Israeli Relations2:00:04 The Way Forward (Will and Mason)2:13:02 Girl Problems: Israel Edition

WEEK 14: Returning from our trip to Israel, we sit down with Shanee Markovitz Kay — an Israeli American and fellow Harvard Law student — for a deeply personal conversation about Israel, identity, and what it has meant to be Jewish at Harvard Law in the aftermath of October 7.

We begin by getting to know Shanee — her background, her path to Harvard Law, and her (as well as our) involvement with the Harvard Law Alliance for Israel — before stepping back to talk about the wide spectrum of Jewish religious and cultural practice, both in Israel and in the United States.

At the center of the episode is October 7th. Shanee shares her personal experience, how it affected her family, her community, and her sense of safety, and what it was like to process those events while being a student at Harvard. We talk candidly about the response to October 7th on campus: the protests, silence, hostility, support, and the emotional and social cost of navigating elite academic spaces during a moment of global attention and polarization.

We then turn to Israel’s response — the moral, political, and strategic questions it raised — and Shanee reflects on what she believes the way forward looks like, both for Israel and for those trying to engage honestly across deep disagreement.

After Shanee leaves, we stay on to offer immediate reactions to the conversation, reflect on our own recent trip to Israel, and zoom out to discuss the history of the modern Israeli state, U.S.–Israel relations, and the broader geopolitical stakes often missing from campus discourse.

We close, as always, with Girl Problems: Israel edition.

This episode is personal, serious, and at times difficult — but it’s an honest attempt to listen, understand, and speak clearly about Israel, identity, and truth in a moment when those things feel especially contested.00:00 Introduction

01:43 Getting to Know Shanee

09:20 Harvard Law Alliance for Israel

12:37 The Spectrum of Jewish Practice

15:42 How Shanee Ended Up at Harvard Law

20:36 October 7th

35:08 The Response to October 7th at Harvard

51:49 Israel’s Response to October 7th

55:24 The Way Forward (Shanee)

1:00:13 Post-Interview Immediate Reactions

1:12:53 Our Trip to Israel

1:41:00 The History of Israel

1:46:19 America–Israeli Relations

2:00:04 The Way Forward (Will and Mason)

2:13:02 Girl Problems: Israel Edition

WEEK 13 (NEW YEAR’S EPISODE): It’s January 1st — a new year, new resolutions, and the usual promises of change. In this episode, we look back at 2025, make rapid-fire predictions about 2026, and ask a harder question underneath all the optimism: Why does it feel like our generation is still waiting for the promises of past generations to come true for us? We open with a bit of reflection on how we shot this episode and why we’re doing it on a hotel bed in Tel Aviv, Israel.

Then we run through rapid-fire New Year’s questions, from cultural and political predictions to lighter bets about where the country and economy are headed in 2026.

The heart of the episode focuses on Gen Z’s stalled trajectory. We talk about how our generation compares to the Boomers at the same age — wages, homeownership, marriage, career stability, and social mobility — and why so many young people feel like they’re falling behind despite doing “everything right.” We discuss delayed adulthood, credential inflation, cultural pessimism, and the growing sense that the promises made to previous generations haven’t yet materialized for ours.

Finally, we close with girl problems — New Year edition: Can you ask a girl to go on Ozempic? Can men and women actually be just friends? And what should New Year’s resolutions look like for couples, guys, and girls trying to build healthier, more intentional lives?

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

01:50 Best and Worst Movies of 2025

05:23 Predictions for 2026!

19:14 Gen Z Is Falling Behind

56:46 Girl Problems: Ozempic

1:03:42 Girl Problems: Can Guys and Girls Be Friends?

1:08:19 Girl Problems: Resolutions for Couples, Guys, and Girls

WEEK 12, THE CHRISTMAS SPECIAL: This episode was filmed in Israel, overlooking the Temple Mount in Jerusalem, just steps from where Christianity began.

We start by walking through some classic Christmas questions — everything from whether you tell your kids about Santa to our favorite Christmas movies and hymns. From there, we talk about what Christianity looks like in the Holy Land today: ancient churches, modern Israel, religious pluralism, and the tension between sacred history and contemporary politics.

We reflect on what it means to celebrate Christmas in a place where the Gospel was first proclaimed — and how proximity to holy ground sharpens questions about faith, tradition, and belief in a secular age.

And because it wouldn’t be our podcast without it, we close with Christmas-themed girl problems. They’re delightful. We promise.

Merry Christmas — and thank you for listening.

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Intro

08:58 Christmas Rapid Fire Questions

29:30 Christianity in the Holy Land

42:11 Girl Problems

WEEK 11: Harvard carries unmatched prestige — but what is it actually like on the inside? In this episode, two Harvard Law students sit down to give an unfiltered look at the most powerful university in the world: the opportunities it creates, the tradeoffs it demands, and the realities that never make it into admissions brochures.

We start with a simple but revealing question: Do you tell people you go to Harvard? When do you say it, when do you dodge it, and what does the name signal — socially, professionally, and culturally?

From there, we ask the question everyone is really wondering: Should you go to Harvard? We break down the numbers — outcomes, salaries, clerkships, BigLaw placement, public interest careers, debt, and Harvard Law’s unmatched alumni network — and then contrast the stats with the lived experience. Is the prestige worth the pressure? Is the price tag justified? And who actually benefits the most from the Harvard system?

We also talk honestly about bias and campus culture — ideological homogeneity, academic freedom, self-censorship, and what it’s like to be conservative, Christian, or politically heterodox inside an institution that overwhelmingly leans left. We discuss admissions preferences, faculty politics, and why Harvard repeatedly ranks near the bottom of free-speech indices.

Along the way, we touch on elite education in America and whether the federal government — including a possible future Trump administration — should challenge Harvard’s tax status, admissions practices, or ideological capture.

Later in the episode, we pivot to broader cultural questions: whether Christians can appreciate art created by immoral artists, how to think about separating art from the artist, and how faith should shape consumption in a secular age.

And, as always, we end with girl problems — dating norms, male passivity, pursuit, boundaries, exclusivity, the “Mike Pence rule,” and how young Christians should think about romance, intention, and courage in a confusing dating market.

If you’re considering Harvard, curious about elite education, or wondering whether the prestige is actually worth the cost — this episode is for you.

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

05:04 Do We Tell People We Go to Harvard?

11:11 Finding Out We Got into Harvard Law

18:33 The Power of Harvard

21:17 Our Weird Grading System

29:10 Ideological Homogeneity

43:01 October 7th Protests

45:13 Should You Go to Harvard?

49:23 The Trump Admin’s Anti-Harvard Campaign

54:17 Separating Art from the Artist

1:04:00 Girl Problems: Video Games

1:09:42 Girl Problems: Azriel’s Two Questions

1:22:33 Girl Problems: Dating Apps Including Weight

1:23:31 Girl Problems: How to Tell That a Girl Likes You

1:27:30 Girl Problems: The Mike Pence Rule