Dear Men: How to Rock Sex, Dating, and Relationships With Women

You've probably heard of penis rings. Maybe you've even tried one!? But there's a another tool almost nobody talks about — the men who've actually explored it say nothing else compares, and yet most guys never even consider it, because of one thing: shame.
Whether it's a marriage that's quietly gone sexless, an erection that isn't cooperating the way it used to, or just curiosity about what's actually out there beyond what you already know, midlife brings up a lot of questions men don't feel safe asking anyone — not their partner, not their doctor, not even their friends.
Karen Bigman gets it. A certified sex educator at 60, she's got 3 fun categories of sex toys she recommends for men. We get into things like: How does a penis pump actually work in real life with a partner — do you pause mid-makeout to grab it, or does it happen before you even get to the bedroom?
And we go somewhere most men never go: the prostate. What's it actually like? Why do the men who've explored it describe it like "watching in high def"? And how do you even start, solo or with a partner?
One stat that stuck with me: according to Mayo Clinic, erectile dysfunction can show up 3-5 years before any other symptoms of heart disease appear. Your body may be trying to tell you something before anything else does.
If you've ever been curious about exploring more but didn't know where to start — or didn't think it was "allowed" — this one's for you.
Work with us
Ready to go deeper than the podcast and take action? Jason and I help you break old patterns and transform your sex & love life for good. To see if you're a fit for our flagship program, Pillars of Presence, book a call here. Start anytime. (https://evolutionary.men/apply/)
Mentioned on this episode:
Karen's site: TabooToTruth.com
Please Her In Bed (Melanie's streaming course on how to talk about sex): www.pleaseherinbed.com
MyHixel — penis rings, and a premature-ejaculation training system
FirmTech — clip-on penis rings, including the Tech Ring (tracks nocturnal erections)
O-Nut — stackable comfort/bumper rings
MV Health (formerly Mystery Vibe) — vibrating prostate massagers
Aneros — prostate massagers
Maude (Shine) — lube I recommend
Memorable quotes from this episode:
"I think the sexiest thing a man can do is ask."
"Your penis health is a barometer of your overall health."
"It's like watching a show in high def."
"The two hardest conversations in relationships are sex and money."
"This is a guy that's actually, like, cares. This is a guy that wants to talk to me. He doesn't just want to get in my pants."
"'I don't care if I ever have sex again.'"
"60 is the new 60."

Edge City is one of the most exciting, fun, engaging, dynamic communities of which I'm a part -- and here I get to interview one of the founders! (This is very exciting for me.)
Edge City runs month-long "pop-up villages" — 500 to 1,000 people from tech, science, culture, and art, gathered in one small, walkable town, building things together. In Timour's words, "It's got the dynamism of a city, with the vibe of a village — that's kind of a design principle for us."
In my words: It's like summer camp meets a tech conference ... and it's also a hotbed of attraction. :)
But what happens when you meet someone in an environment where you absolutely will run into them again? What if you don't want to make her uncomfortable by asking her out? How do organizers think about this?
As Timour puts it, "We are in a weird time when it comes to dating.” But don't worry -- we discuss the anonymous "crush" feature that could change everything.
We also get into the dating dynamics at the village specifically, including my feeling of being surrounded by attractive men and yet noticeably under-approached. We cover the couple whose second date really was an entire month-long event, and the strange twist where Timour says this is actually the opposite of Burning Man's infamous "playa romance" phenomenon.
If you've ever wondered whether there's a real-world alternative to the apps — something that isn't just another platform — this one's worth your full attention.
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Come to Edge City!
The next Edge City is in Goa, India from Oct 11–Nov 1. Plus there's a smaller, 30-person trip to Bhutan from Nov 11–19. Use code DEARMEN for 20% off Goa tickets. Details at edgecity.live.
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Work with us
Ready to go deeper than the podcast and take action? Jason and I help you break old patterns and transform your sex & love life for good. To see if you're a fit for our flagship program, Pillars of Presence, book a call here. Start anytime. (https://evolutionary.men/apply/)
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Mentioned on this episode:
Edge City: upcoming events in Goa, India (Oct 11–Nov 1) and Bhutan (Nov 11–19)
Questions about Edge City? Email DearMenPodcast@gmail.com
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Memorable quotes from this episode:
"I felt like there were all these attractive men, and no one was approaching me."
"We've even had a few kids conceived at or because of Edge."
"I don't want to be the weird guy who's approaching... what if that makes them uncomfortable?"
“It was about how alive I felt in that environment.”
“It’s exponentially more meaningful than a one- or two-day conference.”
“There is the serendipity of running into people that feels magical.”
“We’re pushing ourselves forward both personally as well as society.”
 “It’s the dynamism of a city with the vibe of a village.”
“Why doesn’t your neighborhood feel communal?”
“We needed from the beginning to have the architecture and DNA that would be welcoming to children.”
 “We grow up and we’re taught to find The One.”
“You need to go through the crucible of, ‘Is this the right person for me?’”

She's successful. She's put together. She seems like she doesn't need anyone. So why does dating still feel impossible for her — and why does she seem so hard to get close to?
The men we work with are almost always intensely curious about what life is like on the "other side." What do single women contend with? What are their biggest dating, sex, and relationship challenges? Here, Violet breaks down 3 top issues frequently faced by single women — the ones most men never clock, because women have gotten so good at hiding them.
We get into why the most "together," successful women are often the most terrified of being seen, and what that has to do with whether she actually notices you making eye contact across the room.
We dig into the hot-and-cold thing — why it happens, why it almost never has anything to do with you, and why the woman across from you at dinner may be carrying more than she's ever said out loud.
And we unpack the unconscious dating pattern nearly every long-single woman is repeating without knowing it — the one Violet says she couldn't see either, until someone lovingly pointed it out.
Plus: the bar story about the guy who approached a whole circle of women, and what has changed in Violet's own marriage after over a decade together.
If you've ever felt like you couldn't figure out how to "get in" with a woman who seems to have it all together — or you're partnered with a woman who runs hot and cold — this one could fundamentally change how you see her.
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Work with us
Ready to go deeper than the podcast and take action? Jason and I help you break old patterns and transform your sex & love life for good. To see if you're a fit for our flagship program, Pillars of Presence, book a call here. Start anytime. (https://evolutionary.men/apply/)
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Mentioned on this episode:
Love Harmonics (Violet's 6-week, $69 program on breaking unconscious dating patterns; open to all genders): [https://violetlange.com/loveharmonics/?affiliate_code=5b90a8]
Episode 153: Her Sexual Healing: How to Support Her and Get Your Needs Met (ft. Violet Lange)
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Memorable quotes from this episode:
"The flower opens and the bee appears. Not, the bee comes by knocking on the door, and then the flower decides to open."
"I want to be seen for all of who I am, and not just in my need."
"It fucking works! It really works!"
"I now have soul-shaking sex with my husband... and we've been together 11 years."
"Your happily ever after starts with you — it's not up to fate, it's not up to some meet-cute. It's really an inside job."

Let's be real: Modern dating culture can suck. Between ghosting, confusion over when to have sex, the commodification of our love lives, and people throwing up old photos on Tinder, Feeld, or Bumble, it's not always clear how to make it work.
But Freya isn't playing by the rules anymore. Instead of sticking with the apps, which can leave both men and women feeling dejected, she's running a full-blown, 3-month public campaign to find a boyfriend ... and she's inviting her entire audience along for the ride.
What's equally as cool is that she's challenging herself on an essentially daily basis to approach men in the wild. We get all up into how this is going for her (how do you approach a guy at the grocery store? What if he's got headphones in? What if he's taken? How does she handle rejection?), and her strong and well-made points about how we could all "do" dating better.
We also dig into the wildest event she's said yes to (hint: 250 people were watching); what happened on her fourth lap around a park after 3 failed attempts to talk to a cute guy walking his dog; and why the little note cards she's been handing out to strangers might be the most old-school-meets-radical dating move going right now.
And a distinction we both come back to: the difference between dominating, being passive, and leading (and why "leading" is the one that actually works).
Work with us
Ready to go deeper than the podcast and take action? Jason and I help you break old patterns and transform your sex & love life for good. To see if you're a fit for our flagship program, Pillars of Presence, book a call here. Start anytime. (https://evolutionary.men/apply/)
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Mentioned on this episode:
Please Her In Bed (Melanie's streaming course on how to talk about sex with women in a way that actually helps them to open up): www.pleaseherinbed.com
Find Freya a Fella (Freya's crowdsourced-boyfriend campaign): freyagraf.com
The Labia Lounge (Freya's podcast on sex and dating, for all genders)
The Man Cave (the org where Freya facilitates workshops for teenage boys on healthy masculinity, emotional literacy, boundaries, and consent)
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Memorable quotes from this episode:
"This is not an empowering place to be that we find ourselves in."
"The bar is very low. It's very close to the ground."
"'No one's ever done that. Like, good on you.'"
"I literally massage vaginas for a living."
"That's basically a precursor to being in a relationship with a man who doesn't make effort."
"97% of women did not mention anything about how hard a man got, or how long he lasted. And 0% mentioned him having a six-pack."
"I want love, I love love, I'm not ashamed to admit it."
"Don't be afraid to write a note -- it's adorable."

"Is your dick going to be synced to porn?"
That's not hypothetical — it's already on the market. Here, intimacy expert Susan Bratton walks me through "weird" phenomena at the frontier of sex tech and AI, including synchronized strokers, tele-dildonics (I'll bet that's a word you've never come across before), role-player game (RPG) worlds where you can get down and dirty with an Aztec warrior woman, and adaptive AI that learns what gets you off and gives you more of it.
But where does this genuinely help? And where can it quietly wreck your dopamine system and/or real-world relationships? We delve into all of it, including the exact device suite that Susan and her boyfriend use for long-distance sex. Imagine being thousands of miles apart, still having synchronized orgasms on video. (I did not expect the "hard-boiled egg" comparison, but you'll get it once you hear it.)
Plus:
How a woman can regnerate her vaginal tissue (YES, this helps if she's dry after/during perimenopause/menopause)
The 96% statistic about what most porn is actually showing you
The ancient technique that separates orgasm from ejaculation
Why penis pumps are not the cheesy novelty you think they are

And a fundamental truth that Susan and I agree on: The best sex tech in the world means nothing without the communication skills underneath it. Plus what I consider the quote of the episode: "I want to live forever and fuck till I die!"
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Come to the retreat!
As of this recording, we have 4 spots left for our Labor Day weekend retreat! Sept 3-7th in Northern California (about 2 hrs north of SF). We work hard to keep it financially accessible, and payment plans are available.
As one man says, "If you're thinking about going, you're already there."
https://evolutionary.men/retreat/
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Work with us
Ready to go deeper than the podcast and take action? Jason and I will help you break old patterns and transform your sex & love life for good. To see if you're a fit for our flagship program, Pillars of Presence, book a call here. Start anytime. (https://evolutionary.men/apply/)
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Mentioned on this episode:
Please Her In Bed (Melanie's streaming course on how to talk about sex with women in a way that actually helps them to open up): www.pleaseherinbed.com
Drive Desire (Susan's full toy/device library): www.drivedesire.com
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Memorable quotes from this episode:
"No one's ever given her these types of strokes before."
"They don't want you addicted to the yoni. They want you addicted to the screens."
"Your dick is a tongue, not a piston."
"You don't owe me an ejaculation."
"How's your hoo-ha doing?"
"When you are a turned-on woman or a turned-on man, you're turned on to life."
"Your sexual vitality and your vitality are two sides of the same coin."