The How to Cheat Podcast

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!

EP 2435 - How Cheaters Get Caught

In this episode of The Teresa Pod, host Teresa Conway dives into how people get caught cheating in their everyday lives. From digital slip-ups to modern surveillance tools, cheaters are being busted in creative ways—and Teresa shares real-life stories, including a surprising case involving a Fitbit.
Episode Highlights:
Text messages & social media mishaps: Common digital mistakes, like sending a message meant for a lover to a spouse.
Fitbit betrayal: A husband was caught cheating after his wife noticed 4 a.m. "exercise" on their connected fitness trackers.
Private investigators: How GPS tracking and surveillance gather hard evidence of infidelity.
Digital fingerprints: Emails, browsing history, and shared devices can expose secrets.
How Cheaters Try to Avoid Getting Caught:
Be aware of digital footprints: Turn off syncing, delete messages, and manage shared devices carefully.
Have plausible excuses: Always have a believable explanation for your whereabouts.
Cover financial tracks: Use cash, private credit cards, or business expenses to hide suspicious transactions.
Quotable: "You're only ever as good as your last lie."
If you're curious about how modern technology exposes cheating—and how people try to avoid it—this episode is for you. Don't miss out!

EP 2434 - Martha Stewart Admits to Affair While Condemning Cheaters

In this episode of The TeresaPod, host Teresa Conway delves into Martha Stewart’s recent revelation about having an affair during her marriage to Andrew Stewart. Teresa examines Martha’s marriage, career transformation, and her complex views on infidelity, exploring the contradictions in how people perceive cheating—even when they’ve done it themselves.
Episode Highlights:
Martha Stewart’s Marriage: A look back at her marriage to Andrew Stewart, their successes, and eventual divorce.
The Confession: Martha reveals in her Netflix documentary that she had an affair, while still condemning men who cheat.
The Duality of Thought: Discussing the contradictory views people hold about infidelity, even when they’ve cheated.
Cheating from Boredom: Exploring why some people cheat, including Martha’s potential dissatisfaction with a “cookie-cutter” life.
Martha’s Reflection: "I could have just been a miserable, has-been housewife, but I didn’t let that happen to myself."
Key Takeaways:
Infidelity can stem from boredom or dissatisfaction.
Even those who have cheated may still hold strong opinions on the subject.
Life is complex, and opinions can evolve over time.
Quotable: "Martha calls cheating men 'pieces of s—' while casually admitting her own affair. It’s a striking example of the duality in how we view infidelity."
Tune in to hear Teresa’s thoughts on how Martha’s story speaks to the complexities of human relationships and self-reflection.
Call to Action:
Don’t miss Martha’s upcoming Netflix documentary, Martha, debuting October 30.
Subscribe to The TeresaPod for more candid conversations on love, life, and relationships.

EP 2433 - Why I Reply on Ashley Madison When I'm Not Looking

In this episode of The Teresa Pod, Teresa dives into the surprising reasons why she replies to men on Ashley Madison, even though her profile says not to message her. She shares insights on the types of men who ignore her boundaries, their confidence, and how she finds curiosity in their persistence. Teresa also discusses how she keeps her profile active for professional purposes, and why some men stand out while others get immediately blocked.
Key Takeaways:
Confidence and curiosity make certain men stand out, even when they ignore clear boundaries.
Teresa replies to men because she enjoys seeing who has the guts to push through her tough profile.
She keeps her Ashley Madison account active to review clients' profiles and offer advice on how they present themselves.
Men who follow her advice stand out by being genuine and respectful, rather than overly sexual or arrogant.
Standing out on dating platforms isn’t about luck—it’s about having an interesting profile, being polite, and sending thoughtful messages.
Quotable Moments:
"I tell men, if everyone’s wearing a green shirt, wear a red one. Stand out."
"Some men show confidence and curiosity, and that’s what allows them to break through."
"I never lead anyone on—I’m here to help men improve, not to play games."
Call to Action: Enjoy this episode? Make sure to follow Teresa for more insights on navigating dating platforms like Ashley Madison. Stay tuned for tips on how to improve your profile and connect with confidence.

EP 2432 - Online Chatting Is Where You Win Her

In this episode of The Teresa Pod, host Teresa Conway dives into the most critical part of your affair strategy: mastering the online chat game. Teresa explains how messaging can make or break your chances of moving from initial interest to a real-life connection. She offers expert tips on how to stand out in a crowded inbox, keep conversations engaging, and close the deal without coming off as desperate.
Episode Highlights:
The importance of a strong, personalized opener
How to keep her attention with engaging, light conversations
Strategies for introducing sexy talk at the right time
Tips for asking for a meet without rushing or stalling
Key Takeaways:
Start with thoughtful, profile-based openers to show you're paying attention.
Avoid interrogating or rushing into sexual topics—let her bring it up.
Ask for a meet within 36-48 hours to avoid becoming a pen pal.
Ready to master your chat game? Get Teresa’s ChatGPT Icebreaker Tool and learn how to take your messaging to the next level!
🎧 Subscribe and get more insights from Teresa Conway, your Faery Godmother of Adultery!

EP 3124 - Affair Sex Is Always Hot

In this episode of The Teresa Pod, Teresa explores the reasons why affair sex is often considered incredibly hot and thrilling. Drawing from real-life stories and expert insights, she breaks down the psychological and emotional factors that contribute to the heightened intensity of illicit relationships.
Episode Highlights:
Novelty: The excitement of a new partner and the thrill of the forbidden keep the energy alive.
Commitment to Pleasure: Affair partners go "all in," leading to uninhibited, passionate sex.
Experience: Older and more experienced partners provide heightened satisfaction through patience and skill.
Fulfillment: Mutual desire and meeting each other's fantasies create powerful sexual energy.
Communication: Open, vulnerable communication makes desires easier to express, deepening the connection.
Key Takeaway: To turn up the heat in any relationship, focus on introducing novelty, committing fully to pleasure, and fostering open communication.
Listen now for a deep dive into why affair sex can be so intensely satisfying!
🎧 Subscribe to The Teresa Pod for more episodes on love, intimacy, and everything in between!