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Digital Dating with Anonymous Andrew

Digital Dating with Anonymous Andrew

Written by: Andrew J. Polizzo
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About this listen

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

The Anonymous Andrew Podcast Studios
Hygiene & Healthy Living Relationships Social Sciences
Episodes
  • Is He Worthy? How to Stop Choosing the Wrong Partner | Dave McLachlan
    Nov 9 2026

    Are you choosing the right partner, or are your emotions making the decision for you?

    In Season 5, Episode 19 of Digital Dating Over 50, host Andrew welcomes ICF-certified relationship coach, author, and creator of Is He Worthy?, Dave McLachlan, for a revealing conversation about dating, attraction, compatibility, and why we sometimes ignore the warning signs right in front of us.

    Drawing from his own experiences with divorce and relationships, Dave introduces The WORTHY Method, a practical framework designed to help singles evaluate potential partners more objectively before becoming emotionally invested.

    Andrew and Dave explore how physical attraction can cloud judgment, why people repeatedly choose incompatible partners, and how identifying your non-negotiables can lead to healthier relationships.

    They also discuss the importance of self-awareness, emotional readiness, and recognizing when passion and chemistry are masking fundamental incompatibilities.

    Can you really measure relationship compatibility? And could a more logical approach to dating help you avoid another heartbreak?

    Whether you're newly single, divorced, navigating dating apps, or searching for meaningful companionship after 50, this conversation offers a fresh perspective on finding someone who truly fits your life.

    isheworthy.com.

    Instagram

    https://www.tiktok.com/@is.he.worthy

    Digital Dating Over 50 explores the realities of modern dating, relationships, technology, and finding love later in life.

    Season 5 | Episode 19 | Guest: Dave McLachlan

    Subscribe and join Andrew for more honest conversations about dating and relationships after 50.

    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 Member of the Podmatch Network!

    A Production of the Anonymous Andrew Podcast Studios

    Anonymous Website:

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    Music: Freebeats.io

    Show More Show Less
    59 mins
  • Finding Love After Divorce: Natalie & Glen's Unconventional Love Story
    Oct 25 2026

    Can 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 Bartanian, an intimacy and relationship coach, and Glen Nielsen, a somatic trauma therapist. Glen was twice divorced and navigating life as a single man when he met Natalie. Their friendship eventually blossomed into romance, and exactly ten years after meeting, they married.

    Natalie and Glen share their unconventional journey, including their 17-year age difference, exploring different relationship styles, and learning how honesty, communication, and self-awareness helped them build a lasting partnership.

    The conversation explores dating app burnout, repeating unhealthy relationship patterns, sexual intimacy, monogamy versus non-monogamy, infidelity, and the challenges couples face as they grow older. They also discuss why accepting your partner for who they are matters more than trying to change them.

    For anyone dating after 50, recovering from divorce, or wondering whether meaningful love is still possible, Natalie and Glen offer a refreshing perspective on relationships, personal growth, and finding connection later in life.

    Connect with Natalie and Glen:

    Website: https://wakeuporbreakup.com

    Natalie: https://nataliebartanian.com

    Instagram

    Facebook

    YouTube

    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 Member of the Podmatch Network!

    A Production of the Anonymous Andrew Podcast Studios

    Digital Dating Over 5o Podcast

    Cultimatum Podcast-The Culture of Cults

    The Weekend Rant with Anonymous Andrew

    Anonymous Website:

    Instagram:

    TikTok:

    Threads:

    Facebook:

    YouTube:

    Music by freebeats.io

    Show More Show Less
    1 hr and 4 mins
  • Dating Over 50: Are You Repeating the Same Relationship Mistakes? | Valerie Greene
    Oct 15 2026

    Are 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 Season 5, Episode 17 of Digital Dating Over 50, host Andrew Polizzo welcomes relationship coach and mentor Valerie Greene for an honest, thought-provoking conversation about emotional availability, relationship patterns, communication, and finding lasting love later in life.

    With more than two decades of coaching experience, Valerie shares how our childhood experiences, attachment styles, and unresolved emotional wounds can influence the partners we choose and the relationships we create.

    Andrew brings his own dating and marriage experiences into the discussion, challenging Valerie with real-life scenarios about arguments, emotional distance, and the difficulty of recognizing when someone simply isn't ready for a relationship.

    Together, they explore:

    • Why we sometimes repeat unhealthy dating patterns even after 50.
    • How to recognize emotional availability before investing months or years in someone.
    • Why healthy couples still argue and how they can repair disagreements.
    • The difference between physical chemistry and genuine long-term compatibility.
    • How to identify your emotional needs, core values, and relationship expectations.
    • Why discussing sexual compatibility and exclusivity matters.
    • How to determine whether someone has truly healed from a previous marriage or relationship.

    Andrew and Valerie also tackle a question many older singles face: Do we really know what we want in a partner, or are we simply carrying our old relationship patterns into a new chapter of life?

    Learn more about Valerie Greene: https://coachvaleriegreene.com

    Valeries Instagram

    Listen, subscribe, and follow Digital Dating Over 50 on your favorite podcast platform.

    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 Member of the Podmatch Network!

    A Production of the Anonymous Andrew Podcast Studios

    Anonymous Website:

    Substack

    Instagram

    TikTok

    Threads

    Facebook

    YouTube

    Show More Show Less
    1 hr and 9 mins
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