Digital Dating with Anonymous Andrew
by Andrew J. Polizzo
Finding Love After Divorce: Natalie & Glen's Unconventional Love Story
About this podcast
Welcome to Digital Dating Over 50 — the podcast where modern romance meets real life after 50.
Hosted by Anonymous Andrew, this show explores the highs, lows, confusion, humor, and hope of dating in our golden years. Whether you’re divorced, widowed, newly single, cautiously returning to the dating world, or navigating dating apps later in life, you’re not alone.
From online dating disasters to meaningful late-life connections, Andrew dives into the realities of modern relationships with honesty, humor, and heart. If you’ve ever searched for advice about dating while gray, dating over 50, or finding love later in life, this podcast was made for you.
Topics include dating apps, texting etiquette, companionship, intimacy after 50, loneliness, second chances, red flags, heartbreak, situationships, and building genuine connection in today’s digital world.
Featuring candid conversations, listener stories, relationship experts, coaches, and unfiltered solo episodes, Digital Dating Over 50 is a relatable and entertaining space for mature adults trying to make sense of modern love.
Because dating doesn’t end at 50 — sometimes that’s when the real story begins.
💛 Honest. Relatable. Insightful. Sometimes hilarious. 🎙️ New episodes bi-weekly.
Interested in being a guest? https://www.podmatch.com/member/anonymousandrewpodcast
#datingover50 #datingwhilegray #datingwhilegrey #midlifedating #relationships #onlinedating #modernromance #digitaldating
Episodes
The newest 50 of 299 episodes
- Finding Love After Divorce: Natalie & Glen's Unconventional Love Story · 1 h 3 min · Season 5 Episode 18Can friendship turn into lasting love, even after years of heartbreak and failed relationships? On this episode of Digital Dating Over 50, Andrew welcomes married couple Natalie…
- Dating Over 50: Are You Repeating the Same Relationship Mistakes? | Valerie Greene · 1 h 8 min · Season 5 Episode 17Are you dating over 50 and finding yourself attracted to the same types of people, experiencing the same arguments, or wondering why your relationships never seem to work out? In…
- Dating Over 50: Getting Your Mojo Back with Ray Schloss · 1 h 6 min · Season 5 Episode 16Dating Over 50: Getting Your Mojo Back with Ray Schloss What happens when dating over 50 collides with health, confidence, energy, and a completely different outlook on…
- The End of Swiping? How HAEVN Is Reinventing Online Dating with Rik Foote · 56 min · Season 5 Episode 15Haven and the next wave of online dating Digital Dating Over 50 host Andrew talks with Rick Foote, founder of Haven, a city-by-city matchmaking network designed to replace swipe…
- She Survived Life on the Streets—and Chose Love | Marty Velasquez · 1 h 9 min · Season 5 Episode 14Summary In this episode, host Andrew welcomes Marty Velasquez, (BTW She is NOT over 50) a vibrant and fearless individual who shares her journey of resilience, creativity, and…
- The One Box He Hasn't Checked: Finding Love After 50 with David Gottfried · 1 h 4 min · Season 5 Episode 13Summary What happens when you've built a successful life, raised a family, and accomplished almost everything you set out to do—but there's still one important box you haven't…
- Dating, Intimacy & Infidelity After 50 with Sara Sloan · 1 h 0 min · Season 5 Episode 12Summary In this episode, Andrew hosts Sarah Sloan, a licensed marriage and family therapist, to discuss the intricacies of relationships, particularly in the context of modern…
- Beyond Dating Apps: How Authenti Is Reinventing Matchmaking | Richard Decker · 53 min · Season 5 Episode 11Summary In this episode of Digital Dating Over Fifty, Richard Decker, founder of Authenti, discusses his innovative dating platform that focuses on intentional introductions…
- Dating Over 50: Is It Chemistry—or Just an Old Pattern? · 55 min · Season 5 Episode 10Digital Dating Over 50 explores how singles over 40 can date with more clarity, less pressure, and more self-awareness. Andrew is joined by Paul Aaron Travis, a certified…
- Dating Over 50: Fix Your Profile, Avoid Scams & Find Better Matches · 1 h 28 min · Season 5 Episode 9Summary In this episode of Digital Dating Over 50, host Andrew speaks with Eric Resnick, a pioneer in online dating coaching. They discuss the intricacies of dating profiles, the…
- She Married at 58 After Being Single Her Whole Life · 1 h 11 min · Season 5 Episode 8Summary In this episode of Digital Dating Over 50, host Andrew speaks with Diane Brandon Moody, a dating and relationship coach who shares her journey of finding love at 58. They…
- Life After Losing Your Soulmate with Derrik Dyka · 1 h 3 min · Season 5 Episode 7Summary In this episode of Digital Dating Over 50, host Andrew speaks with Derek Dyker, author of 'Good Grief Travel.' Derek shares his journey of coping with the loss of his…
- Can Your Marriage Survive Erectile Dysfunction? | Gaylen Wilson · 1 h 9 min · Season 5 Episode 6Summary In this powerful episode of Digital Dating Over 50, Andrew sits down with relationship coach and heart transplant survivor Gaylen Wilson, whose remarkable journey took…
- Why Women Over 50 Lose Desire... and How to Get It Back · 1 h 9 min · Season 5 Episode 5Summary In this episode of Digital Dating Over 50, Andrew and Caroline Hood discuss the evolving landscape of dating and sexuality for individuals over 50. They explore themes of…
- Why Women Over 50 Hire Male Companions · 1 h 3 min · Season 5 Episode 4Summary In this conversation, Andrew hosts George Goulburn, an Australian professional companion, who discusses the nuances of companionship versus escorting, the importance of…
- Dating Red Flags: Cray—The App That Could Save Your Heart · 1 h 3 min · Season 5 Episode 3Summary In this episode of Digital Dating Over 50, host Andrew interviews Justin Smith, the founder of the Cray app, designed to enhance relationship safety by identifying red…
- Sex, Dating & Desire After 50 with Suzanne Noble · 1 h 9 min · Season 5 Episode 2Summary In this engaging conversation, Andrew and Suzanne Noble explore the complexities of dating, sex, and relationships for individuals over 50. Suzanne shares her journey of…
- Dicks I've Met Online: Dating, Divorce, and Reinvention After 50 · 1 h 4 min · Season 5 Episode 1Dicks I've Met Online: author-Bren Marrick shares her candid journey through online dating after fifty, exploring relationships, self-discovery, and the surprising world of…
- A Year in Review! Whats coming in 2026! · 38 min · Season 4 Episode 44S4 Ep#44 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- The Hundred Man Plan with Misty O'Hara · 47 min · Season 4 Episode 43S4 Ep#43 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- What Foods Do You Eat To Get in the Mood? · 41 min · Season 4 Episode 42S4 Ep#42 Summary In this episode, Andrew interviews Amy Reiley, an expert on aphrodisiac foods. They discuss the concept of aphrodisiacs, exploring how certain foods can enhance…
- Navigating High Conflict Divorces · 48 min · Season 4 Episode 41S4 Ep#41 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Let's Talk About Sex with Keri Green LMFT · 55 min · Season 4 Episode 40S4 Ep#40 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Navigating the Wild World of Online Dating: Insights from Author Catherine Berra · 46 min · Season 4 Episode 39S4 Ep#39 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Understanding Gender Identity: A Journey with Dr. Amethysta Herrick · 1 h 1 min · Season 4 Episode 38S4 Ep#38 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Dr. Moss - Dating, Mental Health, & Diagnosis · 53 min · Season 4 Episode 37S4 Ep#37 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- The Friending App - Be lonely no more! · 44 min · Season 4 Episode 36S4 Ep#36 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Understanding Toxic Relationships (and realities shows) with Kate Mageau · 45 min · Season 4 Episode 35S4 Ep#35 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- The Scarlet Edit: A Journey of Vulnerability · 40 min · Season 4 Episode 34S4 Ep#34 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Is the Purpose of Dating: More Than Just Finding a Partner? · 53 min · Season 4 Episode 33S4 Ep#33 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Navigating Love Addiction in Digital Dating · 47 min · Season 4 Episode 32S4 Ep#32 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- The Rise of Content Creation in Dating · 38 min · Season 4 Episode 31S4 Ep#31 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Open Relationships: A New Norm? · 48 min · Season 4 Episode 30S4 Ep#30 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Navigating the Chaos of Relationships · 1 h 5 min · Season 4 Episode 29S4 Ep#29 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Navigating the Modern Dating Landscape · 55 min · Season 4 Episode 28S4 Ep#28 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Marni Kinrys (Ask Women Podcast): Confidence, Attraction & The Wing Girl Method · 56 min · Season 4 Episode 27S4 Ep#27 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Somatica-Attachment Style Coaching · 54 min · Season 4 Episode 26S4 Ep#26 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Luma Luxury Matchmaking · 46 min · Season 4 Episode 25S4 Ep#25 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Unlocking Sacred Sexuality w/ Melissa Louise · 56 min · Season 4 Episode 24S4 Ep#24 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- How to Get Laid on Tinder w/ Author Maureen Pound · 48 min · Season 4 Episode 23S4 Ep#23 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Navigating the World of STIs · 49 min · Season 4 Episode 22S4 Ep#22 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Unlocking the Secrets of Friendship w/Shane Gerhard · 51 min · Season 4 Episode 21S4 Ep#21 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- The Art of Starting Over with Shaunna Lee · 50 min · Season 4 Episode 20S4 Ep#20 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Lannette MILF Manor Part2 -The real Story! · 59 min · Season 4 Episode 19S4 Ep#19 Part 2 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee!…
- MILF Manor's Lannette West Part 1 · 53 min · Season 4 Episode 18S4 Ep#18 Part 1 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee!…
- OnlyFans Pepper Kat (what more do you need?) · 47 min · Season 4 Episode 17S4 Ep#17 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Digital Dataing with Cupid AI : A Conversation with Eric McHugh · 45 min · Season 4 Episode 16S4 Ep#16 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- The Impact of Porn on Modern Relationships · 55 min · Season 4 Episode 15S4 Ep#15 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- The man is the leader, right? · 52 min · Season 4 Episode 14S4 Ep#14 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…
- Spotting a Narcissist w/Kim Foster · 50 min · Season 4 Episode 13S4 Ep#13 Want to be a guest on the podcast? Send Andrew a message on PodMatch, here: https://www.podmatch.com/member/anonymousandrewpodcast Please buy me a cup of coffee! Proud…







