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Digital Dating with Anonymous Andrew

Digital Dating with Anonymous Andrew

Written by: Andrew J. Polizzo
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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
  • Why Women Over 50 Lose Desire... and How to Get It Back
    Jul 13 2026

    Summary

    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 empowerment, body image, and the importance of intentionality in relationships. Caroline shares insights from her upcoming book, 'Sex Begets Sex,' emphasizing that desire can improve with age and that women should embrace their bodies and sexuality. The conversation also addresses common myths about sexual desire and the significance of maintaining connection and intimacy in long-term relationships. In this conversation, Caroline Hood discusses the complexities of desire, intimacy, and communication in relationships, particularly focusing on female sexual agency and the impact of aging on sexual desire. She emphasizes the importance of responsive desire, the need for open communication in long-term relationships, and the normalization of discussions around sexual health and pleasure. The conversation also touches on the challenges faced by couples as they age, including hormonal changes and the importance of mutual understanding and support in navigating these changes.

    YouTube Version Here : https://youtu.be/leni9ku5ILQ

    .Carolines Book Sex Begets Sex -To be released soon

    S5-Ep#5

    Caroline Contact:

    Website

    Instagram

    Threads

    Substack

    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:

    Discord Chat Invite Link: https://discord.gg/mS7RAe4gGD

    Instagram:

    TikTok:

    Threads:

    Facebook:

    YouTube:

    Show More Show Less
    1 hr and 9 mins
  • Why Women Over 50 Hire Male Companions
    Jul 6 2026

    Summary

    In this conversation, Andrew hosts George Goulburn, an Australian professional companion, who discusses the nuances of companionship versus escorting, the importance of communication and safety in client relationships, and the unique offerings he provides to women over 50. George shares insights into his journey into this profession, the challenges of the dating landscape for older women, and the transformative experiences he facilitates for his clients. In this conversation, George Goulburn discusses the evolving dynamics of dating for individuals over 50, emphasizing the emotional needs of women in this age group, the importance of pleasure in adult relationships, and the necessity of safety and consent. He also addresses common mistakes made by men and women in dating, the fear of communication, and the traits shared by repeat clients. The discussion highlights the significance of connection beyond transactional encounters and offers advice for those who have given up on dating.

    S5-Ep#4

    George Contact:

    Website

    Facebook

    YouTube

    Instagram

    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:

    Discord Chat Invite Link: https://discord.gg/mS7RAe4gGD

    Instagram:

    TikTok:

    Threads:

    Facebook:

    YouTube:

    Show More Show Less
    1 hr and 4 mins
  • Dating Red Flags: Cray—The App That Could Save Your Heart
    Jun 29 2026

    Summary

    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 flags and manipulative behaviors. Justin shares his personal journey of betrayal that led him to create the app, emphasizing the importance of recognizing warning signs in relationships. The conversation explores the app's features, including the Cray Score and Schemer Score, which help users assess their partners' behaviors. The discussion also highlights the app's relevance for older adults navigating the dating landscape after significant life changes, such as divorce or loss. In this conversation, Justin Smith discusses the challenges of modern dating, including the prevalence of scams and the importance of recognizing red flags in relationships. He emphasizes the need for technology to enhance dating safety and proposes innovative solutions through his app, Cray. The discussion also touches on generational differences in dating behaviors and the potential for creating safer dating environments. Justin shares insights on love bombing and accountability in relationships, while also addressing the skepticism surrounding dating apps and technology.

    S5-Ep#3

    Justin Smith contact:

    Cray App Website

    Instagram

    TikTok

    Linkedin

    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:

    Discord Chat Invite Link: https://discord.gg/mS7RAe4gGD

    Instagram:

    TikTok:

    Threads:

    Facebook:

    YouTube:

    Show More Show Less
    1 hr and 3 mins
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