PODCAST · society
Dating to Win
by Matt Russo
Dating to Win is a real-talk podcast about modern dating, relationships, and self-awareness in today’s world. Hosted by Matthew Russo, the show explores why dating feels harder than ever—and what actually works in 2025.This isn’t surface-level advice or recycled dating clichés. Each episode dives into the emotional patterns, habits, and mindset shifts that shape how we connect, commit, and protect ourselves in relationships. Topics include emotional availability, commitment issues, dating after divorce, situationships, rejection, confidence, masculinity, and what women actually notice about men—often when they’re not in the room.Dating to Win is for men (and women) who want clarity, not confusion. Growth, not games. Honest conversations about love, attraction, self-respect, and why so many people sabotage relationships without realizing it.If you’ve ever wondered:Why dating feels exhaustingWhy good connections fall apartWhy people pull away when things get seriousOr how to show
Episodes
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Can Democrats and Republicans Date? When Politics Gets Personal
Can Democrats and Republicans date successfully, or have political differences become a dealbreaker? In this episode of Dating to Win, Matt Russo explores what happens when dating, political beliefs, and personal values collide. Can two people disagree about politics and still feel understood and...
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What Women Actually Want in a Man (It’s Not What You Think) | GS Youngblood
What women actually want in a man may have less to do with saying the perfect thing and more to do with how he shows up when a relationship gets difficult. On this episode of Dating to Win, Matt Russo talks with author and relationship coach GS Youngblood about healthy masculinity, attraction…
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When Intelligence Doesn’t Protect You From a Romance Scam | Dr. Jonathan Farley’s Story
Can intelligence and education protect someone from a romance scam? Dr. Jonathan Farley is a Harvard-educated mathematician who earned his doctorate from Oxford. Yet despite approaching love analytically, asking approximately 250 questions, traveling to Siberia, meeting his future wife’s family,...
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Romance Scam Victim Lost $1.6 Million in Crypto Scam | Lang’s Interview
In this powerful Dating to Win interview, Lang shares how a six-month romance scam turned into a devastating cryptocurrency scam that cost her approximately $1.6 million. Lang is educated, successful, articulate, and works as a nurse practitioner. She had sold two homes and was planning a fresh...
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They Look Like Romance Scammers but Run Billion-Dollar Crime Networks | Erin West
Most people think romance scams are just fake dating profiles and stolen photos. Erin West explains why many modern romance scams are much bigger than that. In this Dating to Win interview, Matt Russo sits down with Erin West, one of the leading voices exposing romance scams, pig butchering…
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Is It Love or Is He Just After Your Assets? Dating Over 50, You Be the Judge
Dating over 50 can get complicated fast — especially when you have to ask: Is this love, or is someone after my assets? In this episode of Dating to Win, Matt Russo tries something different. Since starting the romance scam series, Dating to Win has received more emails from viewers over 50 who…
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Personality Is Everything in Dating: Why Looks Aren’t Enough
Personality is everything in dating because looks may get attention, but personality creates chemistry, connection, comfort, and real attraction. In this episode of Dating to Win, Matt Russo talks about why personality matters so much when a woman is deciding whether she feels chemistry with you....
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The Romance Scam That Destroyed Her Life | Jennifer’s Story
In this episode of Dating to Win, Jennifer shares the powerful and disturbing story of how a romance scam destroyed her life. What began as what she believed was a real online relationship slowly turned into emotional manipulation, financial devastation, and the loss of her home. But Jennifer’s...
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You Have Friends But Still Feel Alone? Here’s Why
You have friends but still feel alone? Here’s why so many people feel lonely even when they are surrounded by people, texts, followers, dating apps, family, and social media. We live in one of the most connected times in history, but emotionally, many people feel more disconnected than ever. You...
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Your Marriage Isn’t Dead… It’s Just Stuck | Save Your Marriage Before Divorce
Before you give up on your marriage, ask yourself one honest question: is it really dead, or is it just stuck? In this episode of Dating to Win, Matt Russo talks about how some marriages may not be completely over — they may simply be buried under pride, resentment, stress, routine, emotional...
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Dating Scammers Exposed: The Victims They Target Most
Dating scammers are not just asking for money — they are building emotional access first. In this powerful Dating to Win interview, romance scam survivor and advocate Beth Hyland shares her story and explains how online dating scammers target victims, build fake trust, use emotional manipulation,...
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Tired of Your Situationship? Do This Instead
Tired of your situationship and not getting clarity? In this episode of Dating to Win, we break down the 5 signs you're stuck in a situationship, why they won’t commit, and what you need to do to finally break free. If you’ve ever asked yourself: “What are we?” “Where is this going?” This episode...
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Dating in 2026 Is Broken… These Real Questions Explain Why
Dating in 2026 is broken — and these real questions reveal exactly why modern relationships feel confusing, inconsistent, and frustrating. If you’ve been dealing with ghosting, situationships, emotional unavailability, or mixed signals, you’re not alone. In this episode of Dating to Win, we break...
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I Lost Half a Million to Online Dating. Here's How It Happened
I lost half a million dollars to an online dating scam… and it started with a simple connection on Tinder. In this episode of Dating to Win, I sit down with Sue, who shares her real story of being targeted, manipulated, and financially devastated by a romance scam that began on a dating app. This...
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Millions Lost to Romance Scams Every Year… You Could Be Next | Dating to Win
Romance scams and online dating scams are rising at an alarming rate, especially for people over 50, and millions of dollars are being lost every year. In this episode of Dating to Win, we break down how romance scams actually work, the emotional triggers scammers use, and why so many smart,...
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Your Relationship Is Already Over… You Just Don’t Know It
Most relationships don’t end with a breakup… they end quietly. In this episode, we break down the real signs your relationship is already over — even if everything seems fine on the surface. If you’ve been feeling emotionally disconnected, questioning your relationship, or wondering how to know...
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Emotionally Unavailable? Here’s What’s Actually Happening in Your Dating Life
Emotionally unavailable? Here’s what’s actually happening in your dating life — and why so many people today struggle to build real, meaningful relationships. In this episode of Dating to Win, we break down emotional availability, why people become emotionally unavailable, and how it impacts your...
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Do Zodiac Signs Really Predict Relationships? (The Truth About Astrology in Dating)
Do zodiac signs really predict relationships, compatibility, and dating success? Or are we giving astrology too much power in modern dating? In this episode of Dating to Win, we break down the truth about zodiac signs in relationships and why there’s no scientific evidence linking astrology to...
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4 Signs They’re Emotionally Cheating (Without Actually Cheating)
Emotional cheating is more common than people think, and most people miss the signs. In this episode of Dating to Win, we break down 4 signs they’re emotionally cheating without actually cheating—and what it really means for your relationship. If something feels off but you can’t prove anything,...
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Why Chasing Happiness Leaves You Empty (And What Actually Works)
Why do so many people feel empty… even when everything in their life looks fine? We’ve been taught to chase happiness. To follow what feels good. To walk away from anything that doesn’t. But what if that mindset is exactly what’s leaving people feeling lost, unfulfilled, and disconnected? In this...
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Premature Ejaculation: Why It Happens and How Men Can Last Longer
Premature ejaculation is one of the most common issues men experience, yet very few people talk about it openly. In this episode of the Dating to Win podcast, we explore the real reasons why premature ejaculation happens and why anxiety and pressure often make the problem worse. Many men assume...
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Your Emotional Immaturity Is Ruining Your Relationships | Dating to Win
Why do so many relationships fall apart over small things? In many cases, it’s not incompatibility — it’s emotional immaturity. In this episode of Dating to Win, we talk about how losing perspective and letting ego control your reactions can quietly damage relationships, friendships, and...
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5 Questions to Ask Before Committing to a Relationship
Before committing to a relationship, most people focus on chemistry, attraction, or the excitement of a new connection. But long-term commitment requires more than feelings in the moment. In this episode of Dating to Win, we break down five important questions you should ask before committing to...
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The Lie Dating Apps Told You About Love
Are you stuck in an endless loop of "talking stages" and situationships? In this episode of Dating to Win, we uncover the uncomfortable truth about why so many high-value people are still single in 2026. It’s not because you aren't good enough—it's because modern dating apps have trained your…
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How to Attract a Woman (Without Chasing or Begging)
How to attract a woman isn’t about money, looks, or begging for attention. It’s about confidence, purpose, emotional control, and leadership. In this short but powerful episode of Dating to Win, Matt Russo breaks down what truly creates attraction — and why most men get it wrong. You’ll learn: •...
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You’re Not in Love — You Slept Together Too Soon
Modern dating moves fast — sometimes too fast. If you’ve ever felt deeply attached to someone after sleeping with them, this episode explains why. What feels like love is often chemical bonding, not emotional compatibility. In this episode of Dating to Win, we break down: • Why sex too soon…
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Am I Dating a Narcissist?
If you’ve ever asked yourself, “Am I dating a narcissist?” it’s usually not because of one argument — it’s because of how you feel after spending time together. In this episode of Dating to Win, we talk about the subtle emotional signs that show up in unhealthy dating dynamics. Not labels. Not...
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Why Children of Divorce Struggle With Commitment
Children of divorce often struggle with commitment, trust, and emotional closeness in relationships — even when they want love. In this episode, we explore how growing up around divorce can quietly shape adult dating patterns, fear of abandonment, and emotional self-protection. This isn’t about...
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Dating After 50: What Actually Matters in Relationships Now
Dating after 50 is completely different than it was in your 20s or 30s — and that’s not a bad thing. At this stage of life, dating isn’t about chasing excitement, proving your worth, or building from scratch. It’s about peace, emotional maturity, compatibility, and choosing a partner who adds…
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Dating Self Sabotage: The Mistake Ruining Your Love Life Right Now
Dating self sabotage is the biggest mistake ruining your love life right now — and most people don’t even realize they’re doing it. In this episode of Dating to Win, we break down why dating isn’t working for so many people today and how your own mindset may be quietly working against you. From...
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Emotionally Unavailable People Ruined Your Love Life — Here’s Why
Emotionally unavailable people can quietly ruin your love life without you ever realizing why the same dating patterns keep repeating. In this episode of Dating to Win, we break down why emotionally unavailable relationships feel intense at first, why they always fall apart, and how emotional...
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If You’re 20–50, You Need to Watch This | Life Advice for Ages 20–50
Life advice for ages 20–50 is rarely talked about honestly, yet it’s the most important guidance many people never receive. In this episode of Dating to Win, we explore why so many people feel confused about life, relationships, and purpose — and why the answers you’re looking for often don’t…
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Situationships - The Good The Bad and The Ugly
In today’s dating world, situationships have become one of the most confusing — and emotionally draining — relationship dynamics people experience. A situationship feels like a relationship… but without commitment, clarity, or direction. You’re emotionally invested, spending time together…
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They Wrote Me Off and Now I’m Building This | Starting Over at 50
Starting over at 50 can feel like the end — especially after losing your business, your marriage, your money, and your sense of self-worth. In this episode of Dating to Win, I share a powerful message inspired by a real letter from a Gen X man who lost everything after COVID and is now rebuilding...
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New Year’s Day 2026: New Beginnings, Growth, and Becoming Your Best Self
Today is New Year’s Day 2026 — and this episode is about more than resolutions. It’s about recognizing that time is short, growth is intentional, and every single day matters if you want to become the best version of yourself. In this motivational audio episode, we talk about why new beginnings...
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How Social Media is Killing Your Love Life
Episode Description Is your phone the third wheel in your relationship? In this episode of Dating to Win, we dive deep into the silent killer of modern romance: social media. From "digital jealousy" to the endless comparison trap, we explore how likes, comments, and DMs are creating cracks in…
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Should You Take Your Ex Back? (Viewer Q&A)
Thinking about getting back together with an ex? In this episode, we tackle the controversial question: Should You Take Your Ex Back? If you are navigating the chaos of modern dating and wondering "is it worth it?", this Q&A session provides the brutal relationship advice you need before you send...
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How Shy People Find Love
Most shy men believe their quiet nature is a weakness in the dating world. They think they need to become loud, extroverted "party animals" to attract women. But the truth is, being shy isn't the problem—it's how you view your shyness that holds you back. In this episode of Dating to Win, we…
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Why 63% of Single Men Have Given Up on Dating | Modern Dating Crisis Explained
63% of single men have given up on dating. In this episode, we explore why modern dating is pushing men to walk away, what this means for women, and whether there's a path forward for both sides. Get real talk on relationship dynamics, dating strategies, and the hidden costs when men check out of...
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Are You Trauma Bonded to a Narcissist? 7 Warning Signs
Are you in a trauma bond or real love? This psychology podcast reveals 7 warning signs of trauma bonding with a narcissist—and why most people miss the most critical red flag. If you're dealing with emotional abuse, gaslighting, or manipulation tactics in a toxic relationship, understanding these...
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Why You Keep Picking the Same Type of Partner According to Psychology
Why do we keep choosing the same type of partner — even when we swear we won’t do it again? In this episode of Dating to Win, Matt breaks down the psychological patterns that pull us toward the same personalities, the same red flags, and the same relationship outcomes… even when we know better....
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Dating Older Women: What Nobody Tells You
Dating Older Women: What Nobody Tells You reveals the truths most people never talk about. Older women bring confidence, clarity, emotional maturity, and an energy that younger men often find magnetic — but the real reasons go much deeper. In this episode, Matt breaks down: Why dating older women...
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Why Dating Apps Are Losing to AI Girlfriends
Why Dating Apps Are Losing to AI Girlfriends — Dating to Win Podcast Modern dating apps feel more like part-time jobs than pathways to real connection. Endless swiping, ghosting, mixed signals, and hours of wasted time have pushed millions of men into dating burnout. But now, a new shift is...
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You’re Not Tired — You’re Unfulfilled: The Real Reason Life & Dating Feel So Heavy
Feeling drained or burned out? You’re not tired — you’re unfulfilled. In this episode, we reveal why life and dating feel heavy and how to reignite purpose, confidence, and energy in 2025. If you’ve been feeling exhausted, burned out, or emotionally numb, this episode of Dating to Win is going to...
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Stop Your Dating Self-Sabotage Now!
Stop Your Dating Self-Sabotage Now If you’ve ever wondered why you keep repeating the same dating patterns, pushing away good people, or sabotaging something that could have been great — this episode breaks it all down. We explore: • Why people self-sabotage in dating • How fear, insecurity, and...
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How Successful People Attract Love: Mindset, Confidence & Emotional Intelligence
Successful people attract love differently — not because of luck, looks, or timing, but because of their mindset. In this episode, we break down the traits that help high-achievers build real connection: confidence, emotional intelligence, healthy communication, boundaries, and relationship...
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Is Life Fair? | Why Life’s “Unfair” Moments Shape Who You Become in Love and Success
Life advice, motivation, relationships, and self-help for men and women. In this Dating to Win episode, host Matt Russo explores how “fairness” — or the lack of it — reveals who we really are. You’ll discover how to shift your mindset, grow through unfair moments, and find meaning in the setbacks...
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Why Are Young Women Dating Older Men in 2025?
Why are young women dating older men in 2025? This episode breaks down the truth behind the growing trend — from confidence and maturity to lifestyle and emotional balance. We’ll discuss why so many younger women are drawn to older men, and why women today are more fit, stylish, and accomplished...
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Can Christians and Atheists Date Happily? | Dating to Win Podcast
Can Christians and atheists truly date happily — or are they destined to clash? In this Dating to Win episode, we explore how faith and logic collide in modern dating — and why some couples make it work despite completely different worldviews. You’ll hear about: How belief systems shape…
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Why Relationships Fail (And How to Keep Yours Alive)
Dating advice, relationship tips, emotional connection, communication in love, and why relationships fail in 2025. In this episode of Dating to Win, we explore the real reasons modern relationships fall apart — from emotional disconnection and lack of communication to unrealistic expectations and...
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ABOUT THIS SHOW
Dating to Win is a real-talk podcast about modern dating, relationships, and self-awareness in today’s world. Hosted by Matthew Russo, the show explores why dating feels harder than ever—and what actually works in 2025.This isn’t surface-level advice or recycled dating clichés. Each episode dives into the emotional patterns, habits, and mindset shifts that shape how we connect, commit, and protect ourselves in relationships. Topics include emotional availability, commitment issues, dating after divorce, situationships, rejection, confidence, masculinity, and what women actually notice about men—often when they’re not in the room.Dating to Win is for men (and women) who want clarity, not confusion. Growth, not games. Honest conversations about love, attraction, self-respect, and why so many people sabotage relationships without realizing it.If you’ve ever wondered:Why dating feels exhaustingWhy good connections fall apartWhy people pull away when things get seriousOr how to show
HOSTED BY
Matt Russo
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Frequently Asked Questions
How many episodes does Dating to Win have?
Dating to Win currently has 79 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Dating to Win about?
Dating to Win is a real-talk podcast about modern dating, relationships, and self-awareness in today’s world. Hosted by Matthew Russo, the show explores why dating feels harder than ever—and what actually works in 2025.This isn’t surface-level advice or recycled dating clichés. Each episode dives...
How often does Dating to Win release new episodes?
Dating to Win has 79 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Dating to Win?
You can listen to Dating to Win on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Dating to Win?
Dating to Win is created and hosted by Matt Russo.
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