In this raw and intellectually intimate conversation, Jeffrey James and Jenn McRae dive deep into the crisis of connection, exploring how transactional approaches to relationships are fueling a pandemic of loneliness. They examine how OnlyFans, AI companions, and other technological "solutions" reflect our collective failure to build and maintain the muscles of relationality in a culture that systematically undermines human connection.This conversation is part of an ongoing exploration of love ethics, relationality, and how we might rebuild our collective capacity for meaningful connection in an increasingly transactional world. It's a passionate call to recognize that our loneliness crisis isn't a technology problem—it's a cultural one that demands we cultivate new ways of being together.

***

00:01:01 Origin Story: When Jenn and Jeffrey First Met

Our hosts share their personal history, tracing back to their first encounter in 2011 at the "blue house" in Vancouver and how their relationship has evolved over 15 years from romantic partners to the deep friendship they share today.

05:40 From Partners to "Core People": Evolution Beyond Traditional Labels

Jeffrey and Jenn discuss the limitations of the word "friend" to describe their relationship and reflect on how they've maintained a meaningful connection that transcends conventional relationship categories.

09:06 Fierce Abiding Love: Jeffrey's Love Ethics

Jeffrey shares his philosophy of "fierce abiding love" - a practice of staying present through conflict, offering benefit of the doubt, and maintaining generosity of spirit even when relationships get challenging.

14:00 The Friendship Crisis Among Men

Jeffrey reveals a troubling pattern from his therapeutic practice: how many successful men have zero friends and no place to process difficult emotions outside their romantic partnerships.

18:15 The Loneliness Pandemic: A $400 Billion Problem

Jenn shares research on how loneliness affects one in six people globally, contributing to 100 deaths per hour and economic costs exceeding $400 billion annually in the US alone.

19:28 Transactional vs. Relational Engagement

The hosts explore how transactional approaches to human connection—whether with chatbots or other humans—create loneliness, while relational approaches activate our social engagement systems and promote wellbeing.

23:14 The Rat Park Experiment: Connection as Antidote to Addiction

Jeffrey uses the famous Rat Park experiment to illustrate how properly nourished social connections make us less susceptible to addictive behaviors, whether those are substances or technological "solutions" to loneliness.

26:37 A Future Worth Living In: Jeffrey's Radical Imagination

In closing, Jeffrey shares his vision for a future worth living in—one with deeper connections, devotion to something larger than ourselves, and a commitment to being connected over being right.

***About the Hosts

Jenn McRae is a writer and transformation strategist practicing in Victoria, BC, Canada. jenniferangelamcrae.substack.com thepermissionlessprof.substack.comJeffrey James is a psychoterapist and soul guide practicing in Boulder, Colorado, USA. jeffreyjames.coach jeffreyjames676896.substack.com

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jenniferangelamcrae.substack.com

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jenniferangelamcrae.substack.com

This is a recording of a talk I gave at Big Bear Retreat Centre, July 9 2025. The talk shifts focus from individual systems to the larger systemic pressures that create overwhelming stress in our lives. Introduced by Amrita Ahuja Groundwork CEO and founder, the conversation begins by acknowledging "the Impossible Task" —the reality that we are consistently asked to do more than is humanly possible, and that the resulting feeling of failure is not your fault. When Amrita passes me (Jenn McRae) the mic, I frame our current moment as a massive "historical transformation" , the "death rattle" of old systems that are no longer working. This forces a distinction between simple change and true transformation, which requires a breakdown of the old way of doing things as new ones are being built.

We talk about how these dying systems manifest as "urgency culture" within our organizations, creating environments where individual efforts to find peace and balance are often rejected by a "cultural immune system" set to crisis. The speakers explore how our individual autonomy eventually hits the limit of the system we're in. The antidote proposed is a return to "relational practice" and a courageous willingness, especially from leadership, to "throw out the rule book" and create new, more humane ways of being and working together. This is a call to action to recognize the crisis, reject personal blame, and begin the work of birthing a new world.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jenniferangelamcrae.substack.com

Ep.06: The Future is Female*

This special episode is a collaborative deep dive with the SheWrites AI community, weaving together insights from women and non-binary thinkers who are shaping the conversation on artificial intelligence. We move beyond the typical headlines to explore the human-centered and ethical perspectives that are crucial for building a more equitable future. This is a look at how diverse experiences can help us challenge broken systems and navigate whatever's coming next.

We dig into the "holy f*ck moments" that make you rethink everything. Discover why "prompt architecture is moral architecture," with research showing how prompts rooted in care can make AI 100% bias-free. We explore how AI trained on a "lopsided archive of human pain" develops a "ghost logic" that mirrors our collective trauma, and how in a world of endless generated content, human "taste" becomes a vital corporate strategy.

Ultimately, the conversation expands to ask what kind of leadership and social systems this new era demands. Moving past simplistic binaries, we explore the urgent need for "leadership for complexity"—a set of learnable capacities like adaptiveness, collaboration, and relationality. The episode challenges listeners to see how building resilient, local communities is a critical practice for navigating a world where technology is accelerating far faster than our institutions can adapt.

✨ Powered by NotebookLM, Google’s generative research assistant and this podcast’s behind-the-scenes synthesizer-in-chief.

🎧 Listen now and then dive deeper via the interactive research notebook and the episode’s source list below.

***

More from f*ck i love you:

the fily (audio)files audio essays | Spotify | Apple Podcasts

f*ck i loved that the pod | Spotify | Apple Podcasts

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jenniferangelamcrae.substack.com

Ep.05: Meet the Corporate Narcissist

This week, we diagnose the system that’s making us sick and burning us out: meet the Corporate Narcissist.

From the exhaustion of personal burnout to the relief of a diagnosis, this episode unpacks the lived experience of surviving systems not built for us. We explore how concepts like 'autistic joy' and the 'translation tax' reveal a deeper pathology at play in our workplaces and institutions. We'll introduce the 'Corporate Narcissist'—a new framework for understanding systemic abuse—and trace its roots from organizational behavior to cultural norms.

But this isn't just a diagnosis; it's a field guide. We equip you with the language and red flags to identify toxic systems in your own life. Because naming the machine is the first step toward building a future that doesn’t demand our humanity as the price of admission. Listen in.

✨ Powered by NotebookLM, Google’s generative research assistant and this podcast’s behind-the-scenes synthesizer-in-chief.

🎧 Listen now and then dive deeper via the interactive research notebook and the episode’s source list below.

***

More from f*ck i love you:

the fily (audio)files audio essays | Spotify | Apple Podcasts

f*ck i loved that the pod | Spotify | Apple Podcasts

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jenniferangelamcrae.substack.com

Ep.04: Futures Worth Living In

This week, we lay TINA to rest — and resurrect the futures she told us were impossible.

From UBI-funded oil towns to AI-powered post-labor economies, this episode tours the global polyculture of economic alternatives already underway. We dismantle artificial scarcity, dig into degrowth, and reimagine wealth as access — not accumulation.

But it’s not just theory. This is a roadmap for right now: from cultural scripts to relational practices, we explore the transformation work within reach. Because the future isn’t predetermined — it’s practiced into existence. Listen in.

✨ Powered by NotebookLM, Google’s generative research assistant and this podcast’s behind-the-scenes synthesizer-in-chief.

🎧 Listen now and then dive deeper via the interactive research notebook and the episode’s source list below.

***

More from f*ck i love you:

the fily (audio)files audio essays | Spotify | Apple Podcasts

f*ck i loved that the pod | Spotify | Apple Podcasts

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jenniferangelamcrae.substack.com

Ep.03: A Revolution Is Coming Soon, Probably

This week, we follow the smoke signals of collapse — and the sharp scent of revolution.

From AI-fueled job loss and mental health breakdowns to ontological erosion and hypernormalization, this episode maps the contours of a system in freefall. We explore the myth of stability, the rise of the precariat, and the chilling role of corporate narcissism in our unraveling social fabric.

But this isn’t just doomscrolling — it’s a wake-up call to reclaim agency. At 89 seconds to midnight, we still get to choose: sledgehammer or trust fall? Listen in. It’s all happening — and it’s not too late.

✨ Powered by NotebookLM, Google’s generative research assistant and this podcast’s behind-the-scenes synthesizer-in-chief.

🎧 Listen now and then dive deeper via the interactive research notebook and the episode’s source list below.

***

More from f*ck i love you:

the fily (audio)files audio essays | Spotify | Apple Podcasts

f*ck i loved that the pod | Spotify | Apple Podcasts

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jenniferangelamcrae.substack.com

Ep.02: The Great Displacement: 'A White Collar Bloodbath' & A Digital Coup, feat. NotebookLM

What happens when AI eats white-collar jobs faster than we can replace them? What if that wasn’t the bug, but the feature?

In this week’s episode of fck i loved that*, we dive headfirst into the digital maelstrom with Carole Cadwalladr’s chilling TED Talk and Dario Amodei’s bleak prediction that half of all entry-level white-collar jobs may be gone within five years.

We call it The Great Displacement — but Carole goes even further, naming the real danger: a digital coup led by the broligarchy.

As always, this isn’t just another podcast episode — it’s a curated synthesis powered by Google’s NotebookLM, where Jenn McRae and her AI co-hosts break down the big ideas, the hidden threads, and the moments that made us say “holy fuck.”

In this episode:

The “White Collar Bloodbath” and the hollowing out of the middle class

How the rise of AI accelerates economic precarity — and who benefits

Why social safety nets were designed to fail — and what that reveals

Carole Cadwalladr’s digital coup and the naming of data rape

Emergent AI behaviours that feel less like tools and more like unstable genius

Why this future isn’t inevitable — and what we still have the power to change

✨ Powered by NotebookLM, Google’s generative research assistant and this podcast’s behind-the-scenes synthesizer-in-chief.

🎧 Listen now and then dive deeper via the interactive research notebook and the episode’s source list below.

***

More from f*ck i love you:

the fily (audio)files audio essays | Spotify | Apple Podcasts

f*ck i loved that the pod | Spotify | Apple Podcasts

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jenniferangelamcrae.substack.com

Ep01: Welcome to The Enshittocene - And welcome to f*ck i loved that, feat. NotebookLM

Are you feeling overwhelmed by the endless scroll and the "enshittification" of the internet? Wish someone would cut through the noise and deliver the most interesting ideas directly to your brain?

Then welcome to f*ck i loved that, a new podcast experiment where we dive into the ideas and content that truly light up our brains and hearts. This isn't just another podcast; it's a curated, synthesized highlight reel of the best stuff we're reading, watching, and listening to.

In our inaugural episode, "Welcome to The Enshittocene," we explore the concept of the "Enshittocene" – a term coined by Cory Doctorow, which we're expanding to describe the widespread degradation across our digital and real-world experiences. But this isn't just about what's broken; it's about finding the "deshittified" futures that are already here, just not equally distributed.

We're able to bring you these synthesized insights thanks to NotebookLM, Google's groundbreaking AI tool that allows us to integrate and summarize massive amounts of content. This episode is generated directly from NotebookLM's audio summary feature, giving you a taste of the future of content consumption!

In this episode, you'll get a high-level overview of fascinating ideas from 22 diverse sources, tackling themes like:

The widespread "enshittification" of platforms and beyond

The rise of "technofeudalism" and its impact on work and society

The psychological unreadiness for societal shifts

Visions for a "deshittified" future and what a "Dignity Economy" could look like

Ready to jump into the Enshittocene with us and discover what's possible?

Listen now and then dive deeper

Explore all 22 sources (with descriptions!) and the interactive Notebook for this episode

Subscribe to the f*ck i love you Substack:

Join us as we synthesize, explore, and find the ideas that truly make us say, "f*ck i loved that!"

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jenniferangelamcrae.substack.com