The How to Cheat Podcast

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.

EP 2440 - What Women Want on Ashley Madison

In this episode, I take you behind the scenes of Ashley Madison to reveal what women are really looking for—and it’s far more complex than the clichés. Drawing on my book, How to Cheat, and real stories from women, we challenge stereotypes about infidelity and uncover the emotional layers beneath it.
Episode Highlights:
Why women seek connection, validation, and intimacy outside marriage.
Debunking the bored housewife myth—real stories of self-discovery.
How women navigate risks with operational security and discretion.
What men get wrong and how to genuinely connect on Ashley Madison.
Key Takeaway:Infidelity isn’t just about sex—it’s about reclaiming agency, feeling alive, and forging meaningful connections.
Quotable Moment:"Even in the world of infidelity, connection is about respect, trust, and understanding."
🎧 Join me for a thought-provoking conversation about love, desire, and human connection.

EP 2439 - The Ashley Madison Lifestyle

Hey folks! I'm trying out Notebook LM to produce these deep dives into my work. I have over 500,000 words published and a number of books. My BF put them all on Notebook LM and am having their podcast tool talk about subjects I guide them towards. It's a work in progress, but I'm super busy, and this is a way to keep sharing. Let me know what you think at teresa@theconwayagency.com!
 
In this episode, we look at the world of Ashley Madison, the dating site infamous for facilitating affairs. From its purpose to its users' motivations, risks, and the strategies they employ, we unpack everything you need to know.
Episode Highlights:
Why people use Ashley Madison: boredom, lack of intimacy, or revenge.
Key risks: blackmail, scams, emotional fallout, and getting caught.
The psychology of cheating and its ethical dilemmas.
Pro tips from Teresa, author of How to Cheat:
Digital security musts like VPNs and burner phones.
Crafting discreet profiles and communicating intentions clearly.
Navigating real-life meetups with safety and discretion.
Key Takeaway:Ashley Madison isn’t just a website—it’s a high-stakes lifestyle. Be honest about your motivations, cautious about the risks, and prepared for the consequences.
Quotable Moment:“Cheating, like life, always comes with risks.”
🎧 Listen now for a deep dive into this secretive subculture.

EP 2438 - About Maddierose's Book - I Was Red_Delicious on Ashley Madison

Exploring the Life of Maddierose: Infidelity, Empowerment, and Connection
In this episode, we explore excerpts from I Was Red Delicious on Ashley Madison, a candid memoir by Maddie Rose. Through her deeply personal narrative, Maddie shares her journey through marriage, infidelity, and self-discovery, offering a raw look at the complexities of modern relationships.
Episode Highlights:
Marriage Challenges: Maddie's "don't ask, don't tell" arrangement with her husband after a health crisis.
Emotional Complexity: Navigating jealousy, caregiving, and family dynamics.
Ashley Madison: Her path to reclaiming sensuality and connection through the dating platform.
Pandemic Pressures: The impact of lockdowns on her secret relationship.
Empowerment: Moments of self-discovery, from standing her ground in marriage to embracing her sexuality.
Lessons Shared: Coaching others on navigating discreet relationships.
Key Takeaways:
Relationships are multifaceted and often defy simplistic judgments.
Empowerment can emerge from life’s most challenging circumstances.
Vulnerability and honesty lead to personal growth and resilience.
Quotable Moment:"It's not about judging or condoning, but understanding the choices people make and the complexity of connection."
Join us as we unpack Maddie's story, challenging societal norms and exploring the pursuit of authenticity.

EP 2437 - Why Complaining About Your Wife Hurts Your Affair

In this episode, I dive into the complexities of affair dynamics, specifically why comparing an affair partner to a spouse can be an instant turn-off. She unpacks the importance of treating an affair as a unique, respectful connection—one that benefits from its own boundaries and an absence of "spouse talk."
Episode Highlights:
The Downside of Comparisons: Why comparing your AP to your spouse objectifies her and kills the mood.
Respect and Boundaries: Setting a "no-spouse-talk" rule to maintain emotional distance and enjoyment.
James Bond, Not Homer Simpson: How to embody an idealized partner without reminders of married life.
Toxic Bonding: Avoiding negative venting that can bring down the affair's positivity.
Key Takeaways:
Respect Matters: Negative comparisons disrespect all parties involved.
Set Boundaries Early: Keep spouse talk out of the affair for a healthier connection.
"In an affair, be James Bond, not Homer Simpson."
Listen in to discover how respecting boundaries can keep your affair fresh and engaging!
Follow Teresa on Substack!
Get a free pdf copy of my ebook — How to Cheat: Field Notes from an Adulteress — by joining my list! Third-party link to ⇨ MY EMAIL LIST!
Become an Ashley Madison insider: The Complete Ashley Madison User's Guide
Get you ChatGPT custom Ashley Madison message writer: Teresa's Ashley Madison Icebreaker Tool
🎧 Subscribe to The How to Cheat Podcast & The Teresa Pod for more on married dating!
 
 

EP 2436 - Women Shouldn't Avoid "Bad" Dating Profiles

In this episode, Teresa Conway challenges the typical red flags women are taught to avoid in men's dating profiles, such as fish pics, gym selfies, empty bios, or bad grammar. Teresa argues that these profiles can actually hide genuine, sincere men who aren’t playing the "dating app game."
Episode Highlights:
Common misconceptions women have about "bad" profiles
Why polished profiles might be a sign of more experience—and even dishonesty
Focusing on physical preferences first when filtering profiles
How to approach messaging men with "bad" profiles and feel them out
Why inexperienced men often make mistakes but could still be worth the effort
The importance of women messaging first and being patient
Key Takeaways:
“Bad” profiles don’t necessarily mean bad guys.
Look for physical traits you prefer and give the conversation a chance.
Don’t dismiss a man based on a poor profile; he might be inexperienced, not insincere.
Quotable: "The perfect profile sometimes is the red flag you're actually looking out for."
🎧 Ready to rethink your approach to online dating? Listen to Teresa break it all down!
Don’t forget to subscribe and rate The Teresa Pod!