The How to Cheat Podcast

EP 2507 - Frida Kahlo's Affair With Leon Trotsky

In this episode of The How-To Cheat Podcast, Teresa Conway explores one of history’s most unexpected love affairs—legendary artist Frida Kahlo and exiled Russian revolutionary Leon Trotsky. Their brief but passionate connection was filled with politics, betrayal, and art. This episode is spoken by Teresa’s digital twin, Jane—an artificial intelligence voice that brings Teresa’s words to life.
Episode Highlights:
How Trotsky found political asylum in Mexico… and a lover in Frida Kahlo
The affair hidden in love letters and spoken in English to avoid suspicion—badly
Natalia Sedova, Trotsky’s wife, and why she probably was not fooled
The role of revenge in Frida’s affair, considering Diego Rivera’s own indiscretions
Why the heat fizzled out and how Natalia forced Trotsky to make a choice
The lasting impact of their affair on Frida’s art, including Self-Portrait Dedicated to Leon Trotsky
Trotsky’s dramatic end—assassination by ice pick, courtesy of Joseph Stalin’s goons
Why passion, like revolution, always finds a way
Key Takeaways:
Affairs can be political, personal, and sometimes… just a little messy
Speaking a different language does not mean your partner is clueless
Love and revenge are often tangled together
If you are going to cheat with an artist, expect to be immortalized
Whether you love art, history, or just a good scandal, this episode offers a provocative look at desire, power, and the choices we make.
Want to learn more?Connect with Teresa on LinkedIn or visit her website at www.adulteryfaery.com.

EP 2506 - The Roosevelt Affairs

In this episode of The How to Cheat Podcast, I dive into the legendary affair of Franklin D. Roosevelt and Lucy Mercer Rutherfurd—how it started, how he got caught, and how his marriage with Eleanor evolved into something...different.
Episode Highlights:
How Lucy Mercer went from Eleanor’s secretary to FDR’s lover
The love letters that nearly ended FDR’s marriage (and why you should never keep evidence)
How FDR’s daughter helped cover up his later rendezvous
Eleanor’s own “friendships” (was she better at cheating than him?)
Why some marriages work better as partnerships than romances
FDR and Eleanor had a marriage by agreement—publicly together, privately independent. Could more of us handle that setup? Let’s talk about it.
🎧 Listen now and subscribe to The How to Cheat Podcast!

EP 2505 - MAGA's Make Affairs Great Again!

In this episode of The How-To Cheat Podcast, Teresa Conway dives into the scandal surrounding Republican Representative Cory Mills from Florida—aka Floridaman.
Allegations of domestic violence and an affair have rocked his political career, and Teresa isn’t holding back on the details. This episode is spoken by Teresa’s digital twin, Jane—an AI voice that brings Teresa’s words to life.
 
Episode Highlights:
🔹 The scandalous mess: Conflicting police reports and changing stories about what did—or didn’t—happen
🔹 Why no one denied the affair itself, revealing more than they intended
🔹 The complicated details: Allegations of violence, accusations of lying, and claims of eczema and jetlag as excuses for bruises
🔹 The risks of affairs: From emotional fallout to physical danger and vulnerability
🔹 How political hypocrisy plays out: Why the GOP doesn’t seem to care about cheating scandals anymore
 
Teresa’s take on how MAGA is “Making Affairs Great Again” by ignoring political consequences
 
Key Takeaways:
🔹 Affairs come with serious risks—emotional, financial, and physical
🔹 Cheating scandals are no longer political career-killers, especially in the MAGA era
🔹 If you’re having an affair, you need a plan to handle potential fallout
🔹 Accountability shouldn’t be selective, even in politics
 
Teresa offers a bold and unfiltered take on cheating, political scandal, and human behavior. Whether you’re curious about the scandal, thinking about cheating, or just love juicy gossip, this episode is for you.
 
Want to learn more?
Connect with Teresa on LinkedIn or visit her website at www.adulteryfaery.com.

EP 2504 - Are You Ready to Have An Affair?

In this episode of The How-To Cheat Podcast, Teresa Conway explores the hidden thoughts and emotions behind long-term marriages where intimacy is missing. This episode is brought to you by Teresa’s digital twin, Jane—an AI voice that speaks Teresa’s words and experiences just as she wrote them.
Episode Highlights:
The emotional turning point that led Teresa to seek out intimacy outside her marriage
A candid look at the thoughts of someone ready to cheat, inspired by a post on r/adultery on Reddit
Wisdom of the Crowd: Advice from the r/adultery community on patience, risk, and emotional readiness
The real risks involved—getting caught, guilt, and emotional consequences
Why it’s crucial to understand your emotional state before starting an affair
Teresa’s journey from paranoia to becoming an expert on cheating—now helping others avoid major pitfalls
Clarifying her mission: Teresa doesn’t encourage cheating but helps people think through the decision and reduce harm if they choose that path
Where to find more resources, including Teresa’s Ultimate Ashley Madison Users Guide, available on Amazon
Key Takeaways:
Patience is crucial for safety and creating more opportunities
Know the risks—emotional turmoil, potential to end your marriage, and the need to lie convincingly
Being mentally prepared is just as important as the act itself
Cheating is a personal choice, but there’s no reason to be bad at it
Whether you’re curious about the mindset of someone on the edge of an affair or looking for advice on navigating the complicated world of infidelity, this episode offers an honest and thought-provoking perspective.
Want to learn more?Connect with Teresa on LinkedIn or visit her website at www.adulteryfaery.com.
Listen now and get a candid look at the choices we make.

EP 2503 - The Dirty Duchess: A Cheater for the Ages

I use a digital twin in this one. It is, as it turns out, very hard to do a podcast about cheating with hub floating around all day...In this episode of The How-To Cheat Podcast, Teresa Conway delves into the scandalous life of Margaret Campbell, Duchess of Argyll—a woman who defied societal norms and turned infamy into a statement of liberation. Often labeled “the Dirty Duchess,” Margaret’s unapologetic approach to sexuality and refusal to conform made her a feminist icon ahead of her time.
Episode Highlights:
The scandal that rocked British high society: Margaret’s divorce from the Duke of Argyll
The infamous Polaroid photos and the mystery of “the headless man”
Margaret’s private diary of lovers and her fearless exploration of sexuality
The double standards of mid-20th-century Britain and Margaret’s fight against them
The price of defiance: public shaming, financial ruin, and her final years in obscurity
Why Margaret Campbell’s story is one of rebellion, liberation, and feminist inspiration
Key Takeaways:
Margaret’s defiance of societal expectations was an act of liberation, not depravity
Her refusal to name her lovers showcased her courage and loyalty
Society’s hypocrisy in punishing female desire while excusing male infidelity remains relevant today
Margaret’s life teaches us to live authentically, unapologetically, and on our own terms
Margaret Campbell wasn’t just a scandalous duchess—she was a rebel who owned her narrative and turned cheating into an art form. Tune in to hear how her story continues to inspire feminists and free spirits alike.
Listen now and explore the liberating philosophy behind living truthfully—even if it means breaking the rules.

EP 2502 - I Don't Care Who My Clients Are

In this episode of the How to Cheat Podcast, Teresa Conway talks about why confidentiality and security are at the core of her approach when working with clients.
Episode Highlights:
Why Teresa avoids personal details about her clients:
Confidentiality builds trust and protects clients’ privacy.
Knowing “just enough” helps create effective profiles without risking exposure.
Example: A long-term client revealed his real name only after years of working together—proving how irrelevant personal details are to the process.
The importance of separating your real identity from your online “cheating persona.”
Avoid using exact details like profession, height, or age, which can make you easily identifiable.
Real-world risk: Suspicious spouses or private investigators may search dating apps to confirm suspicions.
Security hygiene practices for protecting your identity:
Create a throwaway email and phone number.
Share minimal details early on when chatting with potential matches.
Gradually build trust before revealing more about yourself.
The universality of cheating:
Infidelity transcends politics, professions, and cultures—it’s part of human behavior.
Famous cheaters like King Charles and Donald Trump serve as examples of its pervasiveness.
The dangers of oversharing:
A cautionary tale of a client who shared his real phone number, leading to a scam and blackmail attempt.
Key Takeaways:
Protect your identity: Start with strong boundaries and limit the information you share online.
Confidentiality matters: Teresa’s approach prioritizes anonymity, so her clients can feel secure.
Build trust slowly: Whether it’s with an affair partner or anyone else, don’t rush into revealing details.
Quotable Moment:
"My approach works irrespective of who the client is. I don’t need to know who you are to help you have a successful affair safely."
Call to Action:
Ready to learn how to navigate an affair with discretion? Listen now to get tips on protecting your identity and setting up a safe online persona.
 
🎧 Don’t forget to subscribe to the How to Cheat Podcast!

EP 2501 - An Interview with Maddierose, My Conway Agency Associate

Welcome to 2025 and the debut of The How to Cheat Podcast! 🎙️ Formerly known as The Teresa Pod, this revamped podcast explores the intricacies of online dating and navigating relationships outside the traditional framework.
In this episode, Teresa brings on her associate, Maddierose, a key figure in her online dating consultancy. Together, they reflect on their professional journey, personal stories, and insights from years of helping clients discreetly navigate the world of online dating and affairs.
Episode Highlights:
Behind the Rebrand: Why Teresa transitioned from The Teresa Pod to The How to Cheat Podcast.
Meet Maddierose: From a writing novice to a trusted partner in crafting dating profiles and coaching clients.
The Power of Connection: How shared experiences around sexless marriages forged their partnership.
Working with Clients: Maddie’s growth from writing profiles to managing client accounts.
Success Stories: How a meticulously crafted process leads to meaningful matches for their clients.
Lightning Round: Insights into Maddie’s life, work, and love at first sight.
Key Takeaways:
A structured, empathetic approach is essential in navigating sensitive topics like affairs.
Good online dating support balances discretion, personalization, and an understanding of human connection.
Even taboo topics deserve a space for thoughtful discussion and support.
Quotable Moment:"I became the resource I needed when I started cheating." — Teresa Conway
💬 Ready to dive deeper? Subscribe to The How to Cheat Podcast and follow Teresa and Maddie as they explore the complex, sometimes controversial world of modern relationships.
📚 Explore More:
Teresa Book - How to Cheat: Field Notes from an Adulteress
Maddierose’s Book - I was Red_Delicious on Ashley Madison
🎧 Subscribe now and don’t miss the next episode!

EP - 2443 - Who is Teresa Conway?

In this episode, Teresa Conway—author, blogger, and unapologetic explorer of human behavior—takes us on a candid journey into her life, work, and philosophy. Known for her provocative book How to Cheat: Field Notes from an Adulteress, Teresa shares the experiences and beliefs that have shaped her, offering a deeply personal and often polarizing perspective on infidelity, feminism, and empowerment.
What to Expect:
Teresa opens up about her upbringing, marriage, and how they shaped her views on relationships.
The motivations behind How to Cheat and why it’s more than a guide—it’s a manifesto on choice and agency.
The ethical and emotional complexities of infidelity: risk, control, and the thrill of desire.
Teresa’s fight against societal double standards and the Madonna-whore complex.
The duality of her life as both a caregiver and an advocate for women’s liberation.
How her mentoring work aligns with her belief in women’s empowerment.
Quotable Moments:
"Infidelity is rarely black and white. It’s a reflection of unmet needs and the human desire for connection."
"I’m not here to tell anyone how to live. I’m here to challenge the rules that make us feel trapped."
Connect with Teresa:
Follow Teresa’s blog for more personal insights and reflections.
Subscribe to the podcast for unfiltered conversations on life, love, and the complexities of human connection.
Teresa challenges us to embrace the messy, complicated truths about ourselves and our relationships. Dive into the conversation and discover a new perspective on love, betrayal, and identity.
🎧 Listen now and join the discussion!

EP 2442 - The Generational Echoes of Infidelity

In this episode, I tackle a profound listener question: Can infidelity run in the family? With insights from How to Cheat: Field Notes from an Adulteress, I explore whether cheating is influenced by learned behavior, emotional voids, or even personality traits like impulsivity.
Episode Highlights:
The potential intergenerational patterns of infidelity.
How childhood experiences can shape adult behaviors.
The role of emotional needs like validation and physical intimacy.
Strategic advice for maintaining secrecy and the toll it takes.
Ethical dilemmas and the possibility of growth after betrayal.
Key Takeaway:Infidelity often stems from unmet emotional needs and past experiences, but breaking negative cycles is possible through self-awareness and conscious choices.
Quotable Moment:"I’d never have cheated if I’d been held like this at home. Sex or not, I missed being held more."
🎧 Listen now for an unflinching look at the human side of infidelity and the lessons it can teach us about love, connection, and self-discovery.

EP 2441 - Mutually Assured Destruction (MAD) - The Cold War Strategy of Modern Infidelity

In this episode, I explore the chilling concept of "Mutually Assured Destruction" (MAD) and its unexpected application to the world of affairs. Drawing from my book, How to Cheat: Field Notes from an Adulteress, I examine how MAD can create a fragile balance in infidelity—where the fear of mutual exposure becomes a strange form of trust.
Episode Highlights:
How power dynamics and shared risk shape clandestine relationships.
Why an imbalance of stakes can lead to manipulation and betrayal.
The emotional toll of living a double life and maintaining secrecy.
Practical tips for navigating the complexities of trust in infidelity.
Key Takeaway:MAD might offer stability in the high-stakes world of infidelity, but it’s a foundation built on fear, not fulfillment.
Quotable Moment:"Infidelity isn’t romanticized here; it’s a calculated gamble with high stakes and no guarantees."
🎧 Join me as I uncover the strategies, risks, and emotional intricacies of this taboo topic.