Dating Apps, Red Flags, and Second Chances at Love | Ep. 115

Dating Apps, Red Flags, and Second Chances at Love | Ep. 115

Author: Karen Bigman September 23, 2025 Duration: 40:24

Dating after divorce can feel intimidating, overwhelming, and even hopeless — but it doesn’t have to be. In this episode, I sit down with Andrea McGinty, America’s top midlife dating expert and author of Second Acts: Winning Strategies for Dating Over 50. From founding It’s Just Lunch Matchmaking to facilitating over 33,000 dates and 10,000 marriages, Andrea has seen it all. She shares no-nonsense strategies for navigating the modern dating world, choosing the right apps, spotting red flags, and building a game plan for your love life. Whether you’re newly single or simply curious about what’s possible, this episode proves it’s never too late for a second act in love.

Timestamps:

00:00 – Welcome & Show Intro

00:35 – Today’s Topic & Guest Setup “Is online dating after divorce a nightmare…?"

02:35 – Why Dating After Divorce Feels Harder

04:45 – The Ocean, Not a Pool: Why Apps Matter

08:05 – Right App for Your City & Stage of Life

09:30 – Biggest Mistake: Quitting After Two Weeks

11:40 – Build a Dating “Business Plan”

13:45 – Values, Communication & Chemistry (The 3 C’s)

16:00 – First Relationship Post-Divorce: Are You Ready?

18:20 – Red Flags on Profiles

20:40 – Stop Texting Forever: Set the Date

23:00 – The Sex-on-First-Date Question

24:50 – Matchmakers vs Apps (Costs & Reality)

28:50 – Paid vs Free App Features

31:30 – Hope, Resilience & Process

35:10 – Phone Call or Not? Expectations & Boundaries

38:00 – First-Date Formats

39:30 – Who Pays? Regional Norms & Chivalry

40:20 – Where to Find Andrea + Outro

Want a deeper look? Watch the full episode on YouTube for a more visual experience of today’s discussion. This episode is best enjoyed on video—don’t miss out!

Karen Bigman, a Sexual Health Alliance Certified Sex Educator, Life, and Menopause Coach, tackles the often-taboo subject of sexuality with a straightforward and candid approach. We explore the intricacies of sex during perimenopause, post-menopause, and andropause, offering insights and support for all those experiencing these transformative phases.


This podcast is not intended to give medical advice. Karen Bigman is not a medical professional. For any medical questions or issues, please visit your licensed medical provider.


Looking for some fresh perspective on sex in midlife? You can find me here:

Email: karen@taboototruth.com

Website: https://www.taboototruth.com/

Instagram: https://www.instagram.com/taboototruth

YouTube: https://www.youtube.com/@taboototruthpodcast



About the Guest:

As seen on Oprah, WSJ, People, and CNN, Andrea McGinty is a professional dating coach, author, and entrepreneur with more than 25 years of experience. Having set up over 33,000 successful dates, she is the founder of two dating companies--It's Just Lunch and 33k Dates--as well as several other ventures, including BabyDagny and Pilatesworks.

Connect with Andrea McGinty:

Website: https://www.33000dates.com

Instagram: https://www.instagram.com/33000dates

Book: https://www.33000dates.com/book


Karen Bigman, a Sexual Health Alliance Certified Sex Educator, Life, and Menopause Coach, tackles the often-taboo subject of sexuality with a straightforward and candid approach. We explore the intricacies of sex during perimenopause, post-menopause, and andropause, offering insights and support for all those experiencing these transformative phases.

This podcast is not intended to give medical advice. Karen Bigman is not a medical professional. For any medical questions or issues, please visit your licensed medical provider.

Looking for some fresh perspective on sex in midlife? You can find me here:

Email: karen@taboototruth.com

Website: https://www.taboototruth.com/

Instagram: https://www.instagram.com/taboototruth

YouTube: https://www.youtube.com/@taboototruthpodcast

Substack: https://karenbigman.substack.com

Take control of your pleasure with my Pleasure Playbook, filled with tips to help you connect with your body and enhance intimacy. Download it now at www.taboototruth.com/pleasureplaybook.

Take control of your pleasure with my Pleasure Playbook, filled with tips to help you connect with your body and enhance intimacy. Download it now at www.taboototruth.com/pleasureplaybook.


In a culture that often whispers about aging and ignores the sexuality of older adults, Taboo to Truth: Life & Sex After 50 speaks in a clear, confident voice. Hosted by certified sex educator and coach Karen Bigman, this podcast transforms hushed conversations into open, honest dialogue. Karen’s straightforward and candid approach dismantles the stigma surrounding midlife intimacy, creating a vital space for education and support. Each episode explores the intricate, real-life experiences of dating, relationships, and physical connection after fifty. You’ll hear practical insights on navigating sex post-divorce, the triumphs of rediscovering desire, and the unique challenges that come with these transformative years. This isn’t abstract theory; it’s grounded conversation about the evolving landscape of pleasure, health, and partnership. By diving deep into topics often left unspoken, the show provides both reassurance and actionable guidance. Whether you’re seeking to understand your own journey or to simply listen and learn, this podcast meets you with expertise and empathy. Karen Bigman ensures every discussion moves from societal silence toward personal truth, making Taboo to Truth an essential listen for anyone redefining what life and intimacy mean in the second half.
Author: Language: English Episodes: 100

Taboo to Truth: Life & Sex After 50
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