Dating After 50? Ask These 10 Questions First | Ep. 155

Dating After 50? Ask These 10 Questions First | Ep. 155

Author: Karen Bigman February 24, 2026 Duration: 6:20

Dating after divorce in your 50s can feel exciting, terrifying, and exhausting all at once. In this episode, I share 10 powerful questions you need to ask yourself before you get emotionally invested.

These questions help you stop chasing chemistry and start choosing peace. We talk about nervous system safety, emotional consistency, authentic self expression, and why you should never date someone’s potential. I also break down the difference between chaos and connection, and why midlife is the time to stop auditioning and start being chosen.

If you are tired of walking on eggshells, second guessing every text, or shrinking to keep the peace, this episode will help you recalibrate. At this stage of life, love should steady you. Not stress you.

In This Episode:

00:00 Intro. Dating After Divorce in Your 50s

00:32 Question 1. Does This Relationship Make My Life Easier or Harder

01:00 Question 2. Do I Feel Calm or On Edge

01:30 Question 3. Am I Chosen or Still Auditioning

02:00 Question 4. Can I Be Fully Myself

02:30 Question 5. Do I Feel Safe Speaking Up

03:00 Sponsor Break

03:40 Question 6. Do Their Actions Match Their Words

04:05 Question 7. Am I Growing or Shrinking

04:30 Question 8. Would I Choose Them If Nothing Changed

04:55 Question 9. Does This Feel Steady

05:20 Question 10. Am I Truly At Peace

05:50 Chemistry Versus Peace in Midlife Love

06:10 Final Takeaway and Call to Action

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



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.

LINKS, EXCLUSIVE VIP DISCOUNTS, COURSES & FREEBIES

🍋 Save 25% off on the Lem using code Taboo25

🛒 Link: Hellonancy.com/discount/TABOO25

🚨 Save 25% on Le Wand using code Taboo25

🛒 Link: https://www.lewandmassager.com

💦 Shop my favorite lube from Pjur

🛒 Link: https://www.pntrac.com/t/8-10991-371921-141081?url=https%3A%2F%2Fwww.babeland.com%2Fsearch%3Fst%3Dproduct%26q%3Dpjur

💋 Hotter, Wilder, Wiser | You’ve mastered everything else in life — now master pleasure! https://www.taboototruth.com/hotter-wilder-wiser


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
Podcast Episodes
The One Conversation That Will Change Your Sex Life | Ep. 161 [not-audio_url] [/not-audio_url]

Duration: 6:13
If you want a better sex life, you need to learn how to talk about sex. In this episode, I break down why most couples avoid these conversations and how that silence creates distance, resentment, and confusion. I walk yo…
8 Things I Wish Every Man Knew About Menopause | Ep. 159 [not-audio_url] [/not-audio_url]

Duration: 6:44
🚨 If you are a man navigating your partner’s menopause and feel lost, check out my NEW course ‘Men Meet Menopause’! AND to celebrate the launch, iI am giving you 20% off with code MMPLAUNCH20 https://bit.ly/MeenMeetMenop…
Why Couples Get Bored In Bed And How To Fix It | Ep. 157 (Part 2) [not-audio_url] [/not-audio_url]

Duration: 16:39
What do you do when the relationship is good, but the sex is boring?In part two of my conversation with clinical sexologist Dr. Stacey Friedman, we talk about what really happens to sexual relationships over time. We mov…
My Experience Taking Testosterone As A Woman | Ep. 158 [not-audio_url] [/not-audio_url]

Duration: 13:16
In this episode, I share a personal story I have never told in detail before. It begins in my early 50s after separating from my husband of 25 years and rediscovering sex in a new relationship. My libido was strong, my e…
We Love Each Other But We Are Not Having Sex. Now What? (Part 1) [not-audio_url] [/not-audio_url]

Duration: 18:20
Are you ever going to have sex again?It is the question so many couples in midlife are quietly asking. Sex has become obligatory. Or it has disappeared. Hormones have shifted. Resentment has built. Communication has brok…