Jade Chang Sheppard was nearing 40 when she started wondering if she was living life to the fullest, including sexually. Was monogamy really her best option? Was she actually bi? What was group sex like?
Rather than seeing the exploration that followed as a crisis or breakdown, she’s embraced it all as a revolution. Today, as the founder of Scarlet Society, she encourages other women over 40 to cultivate sexual wellbeing and confidence.
Learn more in this week’s Girl Boner Radio episode!
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“A Sexy Midlife Awakening: Jade Chang Shepherd”
a Girl Boner Radio transcript
Jade: So I had time to think through, okay. I’m pretty much having what society calls a midlife crisis right now, except it didn’t feel like a crisis to me. It felt revolutionary. What I actually like to call it now is like a midlife awakening… So that’s when I got really real about my marriage. I just started feeling like, oh God, I really want to explore a lot of different things. I basically put everything on the table.
[encouraging, acoustic music]
Jade Chang Shepherd is a successful serial entrepreneur. And decades before her “midlife awakening,” she was growing up in what she described as “a pretty conservative immigrant household,” where talking about sex was especially taboo.
Jade: I was basically self-taught when it came to sexuality. I basically just explored on my own,
She said that wasn’t the greatest experience, trying to learn the ins and outs with her first boyfriend. In fact-
Jade: I mean, I basically got pressured into sex the first time by like, “well, we’re boyfriend and girlfriend now. You know what that means,” you know. Not that I didn’t want it. I did. I had all those sexual urges that any teen had.
It’s just that everything felt…mixed up. Especially given her conservative religious surroundings.
Jade: I was going to church at the time and I was a part of a youth group. And then, you know, my parents never talked about it, so I just knew nothing except for what my part of society told me, so beyond not knowing anything, I was just like riddled with guilt and, it just was not a nice experience, but yet I had all these urges and they felt really good and sex itself was really fun, but I was like also worried about getting pregnant and no one talked to me about any kind of birth control.
And I was like so worried about, you know, getting pregnant but yet I really wanted to have sex. So it just was so confusing and such a hard time. And teenage years are hard enough as it is. Like, why don’t we talk to our kids about this kind of stuff? Why don’t we teach them how to do it right? Instead of nowadays they learn by porn. We didn’t even have that back then, you know?
Now that I look back on it, I’m like, God, that could have been like a really beautiful, fun teenage experience. And yet it just, it just wasn’t.
August: Yeah. So what was your sexuality like, your self exploration or sexual discovery journey from say after high school through your early adult years?
Jade: Yeah. Well, I was still really involved in this Christian kind of youth movement. I was in Texas and did that through most of college and I was also an athlete in college, so I was pretty heads down. And it wasn’t until kind of after college where I kind of shed all that religious stuff. And I was like, you know what, it’s time for a fresh start for me.
This is not working, it’s not jiving with me. And I I just found out I was actually a really sexual person. And so through my twenties, I really had a blast. I had a really good time. But I was still young and also a little bit naive.
So I really wasn’t sure what to do with myself. Other than I just like liked having sex a lot.
I hate the word regret because I just don’t have a lot of regrets in life, but I do wish that I had explored a lot more in my twenties and thirties.
My thirties were just all about having kids. I have three kids. I was married to this wonderful man, and it was just all about marriage and having kids and then building my business, which I’ve been really, really blessed with and really lucky with my entrepreneurial journey.
So like thirties were just, that was it. It was just crazy. And I kind of thought, Am I turning asexual? What’s wrong with me? I just didn’t have those same urges that I had when I was in my twenties. I don’t wanna stereotype for everyone, but for me, children were really kind of like a little bit of a libido buzz kill.
That’s really common, by the way, for folks of all genders, especially during those baby months. Even after those “babiest” months had passed, though, Jade said still felt off. And at age 38, she felt yearnings to explore ethical non-monogamy.
Jade: Because we were still really good friends and we had a good connection and we had these three beautiful children and we had like a really good life, you know, and I just wasn’t at a point where I was like, ready to let that go.
So she it brought up to him-
Jade: And he was like, Whoa. He was not into it. I think he just took it really personally, like, oh, must mean there’s something wrong with me, you know?
And it’s never just one sided. Two people make a couple, but that basically kind of started this like downhill of our marriage. It had just pushed me to want to explore more this concept of why does society expect that it’s death till us part? And all of these things, these social constructs that I was taught was like, this is how it is. I just started questioning them.
Monogamy felt like a default she had learned was the only way, versus something that felt authentic. It wasn’t a thoughtful choice she had made. Given the choice, would she have picked it?
Jade: And my daughter at the time, my youngest turned one and I got back into the ocean and surfing again. And that gave me an excuse to go on trips myself. So I started doing that again and just really coming into what I thought was my own identity again.
And my business had been off the ground for a while. So I put in a whole executive team and I didn’t really have to manage the day to day of that anymore. So I had time to just think through, Okay. I’m pretty much having what society calls a midlife crisis right now, except it didn’t feel like a crisis to me. It felt revolutionary. What I actually like to call it now is like a midlife awakening. [bright, ambient tones]
And I kind of felt like, wow, I’m actually so blessed to be able to have this opportunity to sit back and think about, okay, my kids, are they’re not grown, but I became people call now a middle mom, you know, like they’re not little babies toddling around and they’re not grown, but they’re good. They’re good. You know? And my business was good. My career was in a good place. And I got the chance to think, okay, how do I want the second half of my life to look? So that’s when I got really real about my marriage.
This was leading up to the COVID-19 pandemic. And near the start of it, during their four months living in the same space together overseas, Jade started really wanting to explore. At that point, sex with her husband was at a standstill.
Jade: I just started feeling like, oh God, I really want to explore a lot of different things, you know? And I basically put everything on the table. I questioned, okay, is there even a chance that I might be bisexual? I really wanted to explore like playing in groups, three and more. And really just explore this concept of non-monogamy, with other people, like other couples. And I wanted to see how they did it and how they did it successfully.
These stirrings grew during the early early months of the pandemic – and by the time those first several months in close quarters ended…
Jade: Both of us were like, “okay, this is it,” after that (laughs).
So they got divorced – they’ve stayed good friends – and Jade started exploring.
Jade: And it was fascinating. It really was like a two or three year – I mean, continuing experiment that fascinates me. And I wanted to explore this understanding of jealousy. I was like, what is this emotion that just eats at people? And that destroys lives and destroys beautiful relationships?
When I started exploring the community, the lifestyle community as they call themselves, I found it to be really beautiful. I found couples where seeing the other person get pleasure in a group experience was both a turn on to that person and that little bit of jealousy did make things more exciting. And I actually saw these things happen in real life. And I wanted to know more. I buy into it. I love it. And I wanna explore it more.
Jade told me that one of her most eye opening experiences came about through the FEELD app.
Jade: I love that app. It’s really, for the alternative community, kink community lifestyle. There’s everything from people who are just totally vanilla and just exploring, and they’re very honest about it. People are really into a lot of different things, lots of different things.
So I met a man on there and he was very open to the point that he was married and that was totally fine with me cuz I wasn’t really looking for anything and I was just looking for connection.
So they talked and made plans to meet in downtown Venice. They had a great time and decided to meet again, and again. It was casual, and they weren’t dating. Just connecting and having rich conversations.
Jade: Then finally about the fourth time, he was like, “you know, my wife really wants to meet you.” And I was like, “okay.” And I said, “I’m sure it’ll be awesome because whoever you’re married to I’m sure is awesome because you’re awesome.”
And we ended up having like two and a half hour dinner with the three of us and we took a walk. And I had a hotel room that night and we ended up going back to my hotel room and it was a really beautiful night. [sensual music]
I remember during dinner telling them that I was really intrigued at their relationship. It was so eye-opening to me and honestly really refreshing that you can just be so honest with a partner.
That honesty included things that they weren’t comfortable with. Jade also played with men in open relationships where a “don’t ask, don’t tell” rule applied. Both the man and his partner had sex “on the side,” without telling each other any specifics.
Then, Jade met someone unexpectedly and things grew serious. It’s someone she’s still seeing today. And she described the relationship as-
Jade: …super interesting because as much as I wanted to explore, like open relationships and non monogamy this man that came into my life had no experience with any of that and was really not into it. And we’re kind of just exploring what that means and how to kind of explore that.
He cares about her desires, including those that don’t match up with his own, so-
Jade: I brought him to a group party a couple months ago. And he was not super comfortable with it and really you could see, he was really struggling with it. So I promptly took us out of that situation and went back home. And we’ve talked about it since, and I think he is ready to try it again with a different mindset and attitude and like a lens on it.
He’s also helped Jade try on a new lens that she is really into. It’s one they’re both enjoying.
Jade: One other aspect of this lifestyle or this kink alternative that I explored was the dominant submissive personas. And I’ve really really gotten into it. And I really love this. I’ve found that I’ve really enjoyed and really enjoy being submissive.
I can’t even explain how mind blowing this was for me, because I am such an alpha female in the world. I own several businesses, have been very successful and I’m like a mom of three and I do have it all and balance it all and to fully embrace this, it’s like not only a release, but it’s also a part of who I am that I found out.
And wow. I feel so blessed that this doesn’t just live in my mind as a fantasy. I am able to like who I am. And it did become a deal breaker for me. Like this was so important that I needed to find a man who was really dominant.
And this guy she’s dating is.
Jade: I remember our first night, I kind of put his hands around my neck and I was like, “how does this feel?” And he gave me this kind of shocked look, but you could tell there was like this little sparkle in his eye.
You know, like men are taught oh, you never like to lay a hand or mistreat or do anything and yes, you never do, but this is not that, right?
They’ve both had to delve into stigmas and misperceptions around kink they’ve absorbed, she said – doing work that many people who explore dom and sub roles have to do.
Jade: To start exploring these fantasies if they want to exist anything other than in their minds.
That’s been a really, really interesting side of exploration that I’m not sure I would’ve been able to explore when I was 20..
August: I love that, first of all, as you were talking about what your life consists of outside of sex, I felt like relief on your behalf that you don’t have to be the one in control of everything. I mean, I know that submissives in a lot of ways have control, you know, that there’s consent and there’s all these things.
But to be submissive in one area of your life where you are so dominant everywhere else.
August: The other thing that really struck me was this really cool way that you decided to explore these alternate communities and trying different kinks and different fantasies , and not just experiencing these activities, but you were also studying relationship dynamics and seeing what might work for you.
The submissive part of you, that was a huge find on the yes side. Were there things that you encountered that you were like, okay, that was cool to try once or I thought I might really love this, but it’s not my thing?
Jade: Yeah. So I mentioned that I tried like playing with women to see if I was bisexual.
I really wanted to explore that and what I found is there’s actually a whole spectrum when it comes to sexuality and it’s not very black and white. I allowed myself to feel whatever I wanted to feel and acknowledge that. I even went on a date with a girl. And both of us were also in the same place. So it was kind of awkward and funny and also really nice that we were both exploring,
But I remember going to that dinner and texting my best friend and being like ” what if she doesn’t look like her picture?” It was just really funny. One girl ghosted me and I was like, I just got ghosted by a girl.
Through play, I have decided that I am what is called circumstantially bi which means I will play in group scenarios and have fun, and I have no issues.
I actually find women like really beautiful to kiss cause they’re really soft. And I love the female shape, but I have no interest in ever having a romantic relationship. That was a really interesting exploration.
August: Yeah, I bet. I’m glad you got to explore it to find out. That’s really important. I hear from a lot of folks, some folks who explore non monogamy and they realize it feels like their true identity, kind of the way you were talking about being more of a submissive in bed, like, “this is what I want always with every partner, no matter what.” And they’re really, really passionate about that. And then I’ve heard from a lot of folks who are like, it really depends on the relationship, depends on the point I am in my life. It depends on if I’m really busy and I just don’t wanna deal with the schedules.
Like there’s so many different things that we don’t think about. I’m curious if you have a sense of your identity around relationship style through this.
Jade: I am still trying to figure that out. So this is my first serious relationship, since really opening up my life to different things. And I am still really figuring out how to navigate this and how I feel with someone that I truly love.
And I find it to be interesting and beautiful, and I can’t wait to see where it leads. I hope that we grow and explore together. We’ve been together for eight months now. And I have come to a place where I believe that I am not able to be truly monogamous for the rest of my life.
And I told him very early on, I said, you know, “I will never look another person in the eye and say, you’re the only person I’m gonna have sex with for the rest of my life. I just can’t do that.” But what that means, I’m not sure. Do we play together? Do we play separately?
Are you okay with playing with me if we wanna have a group play or threesome? Are you okay if there’s another man there? And we’re just starting to explore this.
We have a trip to Vegas planned for October and we’re gonna go all out. I’ve planned to go to two strip clubs and get a private room. And he gave me this funny look and he is like, “why?” And I was like, “well, first it’s like a strip club, so it’s transactional, there’s really not much to be worried about there, but yet it’s sexy and there’s a lot of sexual energy.”
So to me that felt like a really safe entry point to kind of play and kind of see how we each feel about it.
Jade is hoping he’ll find it sexy and that they’ll both get to see how their sexual energy plays out together in that scene. Meanwhile, they’ve been exploring in other ways.
Jade: One thing I did bring him to was this intro to BDSM class. And there were like eight or nine other couples there and he really dug that and got into that.
So that was pretty fun. Yeah.
August: I love that you’re exploring together and meeting each other where you are, cuz it sounds like you both have had to, which is what happens in a couple, right? You don’t have two identical people, nobody wants that. like we don’t want another us. And so you both have different desires and comfort levels and it sounds like there’s a lot of mutual respect that you’re working together and having these conversations, which is so big and something that I think a lot of folks struggle with.
Jade: Yeah. And I think that this is another thing that just comes with being a little older, being in my forties. Like, I don’t know that I would’ve had the communication or the thought process kind of skills in my twenties to be able to navigate these talks.
The lifestyle is very communication heavy. Where I felt in my marriage like we could get by without talking too much about deep things, it was fine, you know? But this kind of stuff, it’s a, it’s an absolute must to communicate nonstop. And I don’t know that I came into this relationship as really like a top notch communicator. So it’s something that I’ve really had to learn and dig in deep. Just the fact that he can’t read my mind has been like a big revelation for me.
[acoustic, encouraging music]
If you’re feeling a bit stuck in your life or want to invite an awakening of sorts yourself, Jade offered a few things – things that have been a big part of her life the last few years:
Jade: I really got into this concept of like the abundance mindset and I know it’s kind of like this catchy thing right now, but I really dug into it and started researching and reading about it. There’s so much visualization that comes with really understanding how you want your life to look and raising your vibration, like your energy to meet that.
It takes a lot of mental energy and a lot of time to think through, okay. How do I want my life to look? And then backing it out from there. So what do I need to change in my life today in order to make it look like what this visualization is? And then you just start from one thing after another. What is it in my life that gives me energy rather than sucks away my energy?
Or what do you want more of, that could use your energy? Also, know this about the awakening you desire, during midlife or any time in your life.
Jade: While it’s a great catch phrase It can be really heavy and it can involve So much fear. This is a thing about the midlife “crisis” or this awakening is it can be awakening, but there’s so much fear of starting over. And I completely understand it.
The fear of being single again at an older age, the fear of starting a new job, or, in some people’s divorce cases, the fear of not having finances, the fear of being alone with your kids. I mean, there’s so much fear, you know, I mean, even the fear of like finding new friends. It is harder to make friendships at our age, and yet we need them more.
Friendships really are important from middle age on. One study, published in the Journals of Gerontology, showed that older adults who regularly connect with friends report more pleasant days, fewer stressful experiences, and better moods. Jade’s whole “revolution” has benefitted her in similar ways.
August: How has your midlife awakening, especially in regard to relationships and sexuality, how has all of that impacted your emotional self and your life as a whole, like beyond sex?
Jade: You know, I feel like I am in the prime of my life.
I really do. And when I was in my thirties and people in their forties and fifties told me that I was like, oh, that’s bullshit. Like whatever, how can that possibly be? And I, I actually really had a hard time with aging, the concept of aging, especially as I moved through my thirties, I was like, oh my God, I cannot even believe that I’m in my late thirties.
And then I turned 40 and I was like, I might as well just like be dead, you know, like mm-hmm . I really was really hard on myself about aging, but after 40, I guess partly because of, you know, these transformational experiences that I have, it just has been less of an issue for me year after year.
And I just accept like who cares it’s a number? It’s how I feel in my mind. And in my body, I feel better than I did when I was 20. And I, you know, I was an athlete back then. Like I looked great, but I was basically abusing my body, you know, sometimes. Mentally, I feel amazing about where I am in my career, like, I wouldn’t trade anything for the experience that I’ve had in the last 20 years, you know, there’s nothing, I would never go back.
Being where I am in life, I just love it. I wanna do everything I can to hold onto where I am now. I just want all women in their forties to find this kind of awakening to take kind of stock of where they are in like every part of their life, their relationships and their finances and their mental health and their physical health and perimenopause and all that stuff. This could be like such a special time. If you don’t get to grasp it, it just slips by.
August: It sounds like a gift that you give yourself and then are giving it to others in so many ways professionally, but I also imagine your family and your loved ones benefit. How has all this exploration and awakening impacted your motherhood, your relationship with your kids?
Jade: Well, I am not sure yet.
I mean, my kids are super resilient and amazing. . They have been brought up in a different environment. Like we started traveling as a family overseas when they were pretty young. And both my ex and I traveled a lot. So we were never both home at the same time a lot.
But my kids finally this year admitted that I was a cool mom. So…
August: That is really big. Cause I think most kids, they realize it later. At least for me. I, I always feel like I wanna thank my parents so much more because I don’t know I was an ornery teenager.
Jade: It was really cute. He’s like, you know, I see other people’s moms and I’m like, my mom is really cool.
August: That is amazing. I love it.
As Jade mentioned, she runs several businesses. The one she most wants you all to know about is called Scarlet Society.
Jade: Which is just like such an amazing passion business. It was started to be all about sexual health and wellness for women over 40 something rather cutting edge, something that was willing to like talk about topics that, other publications couldn’t or wouldn’t talk about.
The platform is editorial, full of articles – and they’ve also branched out into YouTube and a podcast. Soon, they’ll be adding a newsletter. They also feature products. Jade’s favorite is called the Aftercare Serum.
Jade: It’s for after sex, when you’re kind of feeling like inflamed, kind of gross, and it’s all natural oils. It makes you feel fresh and clean and a little bit cooler. It’s got that tingly-cool to it.
Jade’s mission is all about helping other women age 40 and up thrive.
Jade: Women over 40 are the most ignored demographic right now in the world. There’s a lot of advertisement towards young moms and women of childbearing age, but once you’re done having kids, to me, it was like, society was saying, well, you don’t need to have sex anymore, right? People are starting to write some articles and some surveys about how women over 40 are portrayed pretty negative light, and yet we are actually more confident than ever, really feel better about ourselves and our place in the world than ever. So I think that is about to change and I really hope Scarlet is like really at the forefront.
Scarlet is all about helping middle-aged women feel more confident. When it comes to cultivating more sexual confidence and pleasure, no matter our age, Jade recommended this:
Jade: Allowing yourself to have fantasies. I think that’s the smallest thing that you can do to an entry to discovering what else you want from your sex life… That bridges the gap between intimacy and eroticism and how it’s necessary. Especially when we grow up in a society that doesn’t accept it.
Just simply allowing ourselves to, to have fantasies and what are they? And now that I think back all the way until I was really young, I did always have these fantasies of being a submissive, you know? And I was always like, why am I having all these taboo fantasies?
But being at a place where you just freely allow yourself to have whatever fantasy you want, you know? Be a submissive, be a Dom, be a Mistress Dom, the gang bang, whatever… All these different things that are super taboo. And then just go and explore from there. Have a fantasy of whatever you want.
Learn more about Jade Chang Shepherd and Scarlet at scarletsociety.com where they help women confidently explore pleasure and sexual health, with the perfect tagline: “the best is yet to come.”
[acoustic chord riff]
*outro music that makes you wanna dance!*
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