How would your relationships be different if you could experience the world from the other side of the gender divide, and understand how a man or woman (whichever you are not) feels and experiences life? Would it bring more compassion for the things that irritate you?

Today's guest has something very few people can offer: a real life perspective on living as both a woman and a man.

Since Jason Hill transitioned he has experienced radical shifts in how people perceive him, how he's treated professionally, how much emotional vulnerability feels accessible, how his sex drive changed, and even how much physical affection is available to him.

In this fascinating conversation, we explore what those experiences reveal about men, women, love, sex, emotional intelligence, and the invisible expectations we place on each other.

We talk about:

• How Jason has been treated as more intelligent and receiving more professional opportunities as a man
• The pressures men can carry with the expectations to provide, earn, protect, and prove their worth
• Why having male privilege doesn't mean life is always easy
• What women usually don't see about men's vulnerability to violence, rejection, and emotional isolation
• Why so many men are touch-starved, and how sex can become one of the only socially acceptable forms of affection
• The surprising ways we're socialized differently as men and women
• Why emotional intelligence can be learned
• How to make the goal of conversations understanding what is actually happening for another person, rather than winning the argument
• What greater empathy across genders could make possible in our relationships

Jason's story invites us to hold multiple truths at the same time: men benefit from systems of privilege and still experience profound pain, loneliness, objectification, and pressure. Women suffer from discrimination and often have assumptions about men that can make it harder for men to feel loved and understood.

The more we're willing to get curious about those contradictions, the more possibility we have for love.

Because emotional intelligence isn't about becoming better at arguing your side. It's about becoming better at seeing the person in front of you.

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Dating feels brutal for so many relationship-ready singles, especially over 40. In this episode, Shana James talks with Adam Cohen Aslatei, CEO of Three Day Rule, about how AI is reshaping modern matchmaking and how AI makes it easier for people to date and find real, emotionally available love. They explore dating burnout, why the apps are failing people, the power of intentional dating, and how AI can even support deeper human connection. A must-listen for those who want to stop unconsciously swiping and start consciously dating and creating meaningful relationships.

Find out how to have the best love and sex of your life!

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We explore what happens when being "the one who saves" starts costing you connection with yourself and others. Brent Perkins joins me to unpack how overgiving and self-abandonment can masquerade as love, and what it really takes to move from trying to be the hero to letting yourself be human. You'll learn to give without depletion, create agreements instead of expectations, and practice the art of receiving love as fully as you give it.

Find out how to have the best love and sex of your life!

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What happens when the woman you love stops wanting sex?

For many men, a fading sex drive feels like rejection, loneliness, or even a sign that the relationship is dying. You may wonder:

Am I still attractive? Does she still want me? Did I do something wrong?

After more than 20 years of coaching men and couples, I've found the answer is usually more nuanced.

Women often don't stop wanting sex. They stop wanting the sex they've been having.

As women move through midlife, many become less willing to settle for intimacy that feels rushed, disconnected, predictable, or focused primarily on their partner's experience. Hormones and health can certainly play a role, but there's another piece that often gets overlooked: desire is relational.

In this episode, I explore a different way of understanding desire—one where it isn't something one partner has and the other needs to get back. Desire is something two people create together.

I share six ways I've helped couples co-create more connection, pleasure, and passion, including becoming a student of your partner, slowing down, moving beyond one-dimensional sex, creating experiments instead of expectations, and learning not to take differences in desire personally.

If your sex life has faded, I hope this episode gives you something you may not have had in a while: hope that the best intimacy of your relationship can still be ahead of you.

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Have you ever looked at someone you love and wondered, What happened to us?

Most people assume relationships drift apart because the spark fades, communication breaks down, or life simply gets in the way. But what if the real reason is much simpler and more hopeful?

In this conversation, bestselling author and executive coach Jamie Smart shares a perspective that has transformed the lives of thousands of people he has coached.

One of my favorite moments is when Jamie talks about how he'd spent years organizing his relationships around avoiding heartbreak instead of creating true love, and what is possible since making that shift.

In this episode, we explore:

The underlying causes of relationships drifting and spark fading

How your "view" changes how your partner appears to you

The downward spiral of disconnection from trying to be "right"

How insight transforms relationships faster than trying harder

The key to make the shift from self-protection to creating true love

Whether you're dating, married, healing from heartbreak, or simply wanting deeper connection, this conversation offers a fresh way of understanding what keeps love alive, and what helps us truly see each other again.

And if you want a deep dive into understanding who you truly are, and what's possible in love and life once you know this, this is an episode for you.

Enjoyed this conversation? Here are a few more resources:

Jamie's Resources:

Learn more: JamieSmart.com

Listen to Jamie's podcast: https://podcasts.apple.com/us/podcast/get-clarity-with-jamie-smart/id1173476690

Explore Jamie's books, including Clarity and Results: Think Less, Achieve More: https://www.jamiesmart.com/jamie-books/

Shana's Resources:

Discover what's keeping you from having the love and connection you want. Take the quiz: https://bestlove.scoreapp.com/

Join the Honest Dating Manual waitlist https://shanajamescoaching.com/honest-dating-manual/

Need support? Schedule a free Love Consultation: https://shanajamescoaching.com/consult

Music from #Uppbeat (free for Creators!):
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Many people enter dating determined to avoid conflict. They smile through uncomfortable conversations, overlook comments that don't sit right, or convince themselves they're being "easygoing." Especially for those dating after 40 or dating after divorce, staying agreeable can feel like the safest way to protect themselves from rejection or disappointment. But according to relationship and dating coach Shana James, this habit often prevents people from discovering whether someone is truly capable of building a healthy relationship.

In this solo episode of Practicing Love, I, Shana James, share the third move in my series on transforming modern dating. While the first two episodes focused on creating an honest atmosphere at the start of a date and staying connected to your own experience throughout the conversation, this episode explores what to do when something doesn't feel quite right.

Most people respond to uncomfortable moments in one of two ways. They either smooth things over and pretend nothing happened or they emotionally check out of the conversation without saying a word. Although both reactions are understandable, neither helps you learn whether the person sitting across from you can handle honesty, curiosity, and emotional intimacy. Instead, Shana encourages listeners to do something surprisingly simple: acknowledge what you're experiencing.

Rather than accusing your date or making assumptions about their intentions, she recommends expressing your own internal experience. A sentence as simple as, "Can I say something honest?" followed by sharing what you noticed in yourself can completely transform the conversation. This isn't about creating conflict or turning a first date into therapy. It's about inviting authenticity.

When you honestly express a small moment of discomfort, your date's response becomes valuable information. They may become curious, defensive, dismissive, or open. Every response reveals something about their emotional maturity and their ability to navigate real relationships.

Drawing from years of coaching experience, I share story of a divorced client who repeatedly invested months into relationships before discovering important incompatibilities. By practising this simple shift, he learned to recognize emotional availability within the first hour of meeting someone instead of months later. The goal isn't to test people or create uncomfortable conversations for their own sake. It's to stop performing and start discovering.

Together, the three shifts in this series create a new approach to dating—one rooted in honesty instead of approval, curiosity instead of performance, and genuine connection instead of self-protection. Rather than hoping love happens by chance, you begin creating the conditions where authentic intimacy can grow.

CHAPTERS

Why Small Moments of Friction Matter in Dating

The Cost of Staying Silent to Keep the Peace

Emotional Maturity vs. Emotional Avoidance

The Third Shift: Speak Your Truth with Honesty

How to Say "Can I Say Something Honest?"

What Someone's Response Reveals About Them

A Real-Life Example of Honest Dating in Action

The Three Shifts That Create Authentic Connection

Building Lasting Love Through Openness and Presence

Final Thoughts: Practicing Love After 40

Website: https://shanajamescoaching.com/

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

Everyone talks about "baggage" in dating.

But what does that actually mean?

If you're dating in midlife, chances are you—and everyone you meet—have lived through heartbreak, divorce, health challenges, parenting, financial ups and downs, grief, or complicated family dynamics.

The goal isn't to find someone without baggage.

It's to discover whether your lives, values, and emotional realities are compatible enough to build something beautiful together.

In this episode of Practicing Love, I sit down with relationship and intimacy coach Karen Bigman to explore what baggage really is, how to recognize the difference between deal breakers and manageable challenges, and why self-awareness is far more important than finding a "perfect" partner.

Together we explore:

Why everyone in midlife brings some form of baggage into dating

How to tell the difference between compatible and incompatible baggage

Why knowing yourself matters more than following dating rules

When to communicate your needs, boundaries, and relationship history

How divorce, children, finances, family dynamics, and health challenges affect dating

Perhaps the biggest takeaway is this:

Your past doesn't have to determine your future.

What matters is how consciously you understand yourself, communicate your needs, and choose relationships that honor who you are today.

Because dating isn't about finding someone with no baggage.

It's about finding someone whose life, values, and humanity fit well with yours.

Karen Bigman is a relationship and intimacy coach, sex educator, and host of the Taboo to Truth: Life & Sex After 50 podcast. She specializes in helping men navigate dating, intimacy, midlife sexuality, and relationships with greater confidence, honesty, and self-awareness. Through coaching, courses, and education, Karen helps people create more connected, authentic relationships in the second half of life.

Website: https://taboototruth.com

Podcast: Taboo to Truth: Life & Sex After 50

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

Take the quiz to find out what gets in the way of finding love: Find Love Quiz

Join the Honest Dating Guide waitlist: https://shanajamescoaching.com/honest-dating-manual/

Schedule a consultation: https://shanajamescoaching.com/consult

Music from #Uppbeat (free for Creators!):
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