WEEK 21: Is Modern Dating Rigged? (With Luis Penichet, HBS & Former Marine) This week we’re joined by Luis Penichet — second-year Harvard Business School student, former U.S. Marine, and founder working on a new kind of dating app. And we go straight at one of the biggest cultural questions facing our generation: Is the American dating system fundamentally broken? We begin with a blunt diagnosis. Dating apps reward dopamine, novelty, and endless optionality — not long-term bonding, sacrifice, or family formation. Swiping trains people to treat each other as consumable profiles rather than covenantal possibilities. We discuss why both men and women are struggling — women facing overwhelming choice and rising expectations, men shaped by pornography and comparison culture — and whether our standards are too high, too low, or just disordered. Luis then shares the idea behind the app he’s building: instead of scrolling through photos, you scroll through simulated conversations. Users create AI agents trained on their views, personality, and values. Those agents interact with other users’ agents first — and you review the conversations before ever seeing a photo. The goal? Shift attraction toward worldview, communication style, humor, and compatibility before physical filtering takes over. We debate whether this could actually rewire incentives — or whether technology will always drift toward superficiality. From there, we pivot to Luis’s family story. As the son of Cuban immigrants, he explains why identity politics and Marxist frameworks are so dangerous — not in theory, but in lived history. We discuss how grievance-based politics corrodes gratitude, how America differs from Latin American revolutionary culture, and why economic resentment can quietly become moral justification for state overreach. Then things get fun. We run through a lightning round of conspiracy theories — which ones are obviously false, which ones are plausible, and which ones we genuinely don’t know what to do with. Instead of dismissing or embracing them wholesale, we talk about epistemic humility, institutional trust, and how to think without becoming paranoid or naïve. Finally, we close with Girl Problems: - Luis speaks for the short kings (he is one):How should women think about height preferences? - Biological clocks and delayed adulthood - And the infamous Alabama Hypothetical Email approachthebenchquestions@gmail.com 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 2:24 Problems with Dating Culture 18:22 Are the Issues with Dating More Deep-Rooted? 37:54 Luis's Cuban Heritage and the Essence of America 57:27 Conspiracy Theories... 1:10:02 Feedback, real quick! 1:13:22 Girl Problems: Short Kings 1:21:05 Girl Problems: Biological Clock 1:24:34 Girl Problems: The Alabama Hypothetical