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

How much does a woman's sexual satisfaction depend on the size, shape, or other physical details of your cock?
According to research out of the UK, this question is on the hearts of a lot of men. To quote this study: "Men showed significant dissatisfaction with penile size, despite perceiving themselves to be of average size."
In other words, it's common, if you're a man, to wonder (or worry) about whether size matters.
Now here's the real question: Do women that sleep with men track this, and if so, how much?
The truth is that there's as much diversity in the world of penises as there is in the world of human beings. And as women who have sex with men, we've seen a whole bunch! Here, we get real about sex, relationships, hookups, play, and cock size.
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Join us!
We've got a few spots left at our live, in-person retreat, September 3rd–7th — five days of embodiment, brotherhood, and doing the work that will actually move the needle. Get in here: https://evolutionary.men/retreat
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Mentioned on this episode:
Please Her In Bed, my streaming course: www.pleaseherinbed.com

Do you want to establish a new, healthier habit, but so far you just ... haven't? For example: eat more veggies; exercise; have a meditation practice; be bolder with women/your woman; or a big one: cease watching porn.
According to a meta-analysis on this exact questions, intentions only account for ~30% of whether someone actually changes behavior — meaning you can be fully committed and clear on what you want to do, and that commitment still barely predicts whether you’ll do it.
The good news? Change is possible; it just doesn’t happen the way you think it does.
We get into the real gap — between knowing and embodying — and cover why some of the smartest, most self-aware men we work with can describe their patterns with PhD-level precision, but still be stuck in the exact same loop years later.
We also talk about the guy who showed up to the work feeling stuck and hopeless ... and who's now having the most fulfilling sex of his life with the healthiest partner with whom he has ever been.
Fair warning: this one might make you rethink how you've been trying to change -- and you might start taking the actions that'll ACTUALLY get you what you want.
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Join us!
We've got a few spots left at our live, in-person retreat, September 3rd–7th — five days of embodiment, brotherhood, and doing the work that will actually move the needle. Get in here: https://evolutionary.men/retreat
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Memorable quotes from this episode:
"You don't know how deep the pond is till you get in there."
"It's the difference between information and transformation."
"Healing your relationship with other men sets you up for success with women."
"Courage is not, 'I know everything's gonna be fine.' Courage is, 'I'm scared and I'm doing it anyway.'"
"There is no replacement for the group."
"The payoff is so grand — but you gotta take some risks, you gotta do the damn thing."
"That guy's got fucking balls and fire ... and he feels so safe to be around."
"Shame is healed in community."

When it comes to sex, dating, and relationships, what is AI good for? And where can it potentially cause damage?
Here, Jason and I go point-for-point — one way AI can support your love life, one way it can harm it — and get into the nuances most people aren't talking about.
We cover what AI is actually good for: crafting the message you can feel but can't quite say; getting unstuck when you're in your head at midnight; brainstorming date ideas that generate real dopamine for the couple; handling the "shit work" of logistics so you can show up more present.
We share the real story of one client whose fight with his wife got a little unstuck through an unexpected AI assist — and the "family assistant" moment that changed everything for a friend struggling to ask for help.
We also delve into in which ways AI can be like emotional porn; what MIT research shows about how heavy AI use impacts mental health and relationships; and why people literally grieved when OpenAI turned down the sycophancy dial.
The deepest cut? AI has no needs. It will never trigger you, never require repair, never push back. And if you spend enough time in that dynamic... you might start to forget that friction is what actually creates intimacy. But real negotiation between two different humans — that's not the obstacle to love. That IS love.
If you're curious about AI and want to use it wisely — without letting it quietly erode the very capacities that make you magnetic — this one's for you.
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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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Memorable quotes from this episode:
"There's a risk she's gonna figure it out."
"What's our agreement or understanding about AI in our relationship?"
"You've got to make sure you're working it, and it's not working you."
"AI can give us the fake sugar version of relationship."
"It doesn't have any needs. It doesn't have any triggers. There's no need to negotiate."
"The friction of relationship is what we learn to work — and it's what makes it meaningful."
"Get really good at friction. If you can be the one in the room who can hang in conflict — that is only going to become more valuable."
"It can be part of your team. It can't be your whole team."
"Safety and trust is built in person with human beings — and most of what we're gauging is how they are being with us, not what they are saying."

"Is this in my head, or is this real?"
Millions of women ask themselves this question -- about their sleep, their mood, their body suddenly working differently than it used to. They can't tell if they can't sleep as well as they used to because they've got two young children ... or whether it's perimenopause.
If you want to be an awesome partner (either now or in the future), listen on! This is the hormonal literacy class you never got that could help with everything.
Here I sit down with Morgan Miller, midwife and co-author of The Cycle Book (with her best friend, sex therapist Laura Federico), to decode what's actually happening in a woman's body as she's in different phases.
We go deep on perimenopause: sleep disruption, night sweats, heart palpitations, ER scares no one warns you about; the anxiety and PMDD that can be a hormonal sensitivity, not an imbalance. There's also the easy, often-missed fix for vaginal dryness, recurrent UTIs, and painful sex (a targeted topical instead of antibiotics).
We also cover why a single blood draw is just "her estrogen at 2pm on a Tuesday" — and why tracking biomarkers (which is actually pretty simple) over a few cycles tells you a LOT more.
Plus a stat that floored me: period-tracking apps are only ~20% accurate at predicting ovulation — wrong roughly 80% of the time.
If your woman has ever been told "everything's fine" while her body said otherwise, and you've felt helpless watching it — this one's for you.
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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:
The Love Field: Hot Love Summer → www.violetlange.com/thelovefield
The Cycle Book: An Interactive Step-by-Step Guide to Tracking Hormones and Knowing Your Body by Laura Federico, LCSW & Morgan Miller, CPM, LM
Work with Morgan & Laura (virtual; they also train providers): www.itslauraandmorgan.com
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Memorable quotes from this episode:
"I feel loved when the men in my life know things about a woman's body."
"Men have a 24-hour cycle, too."
"Vaginas are so smart — they're self-cleaning systems."
"Don't get pigeonholed into the algorithms; you're not every human."
"It's like learning a new language. Once you learn it, you can't unlearn it."
"Is this my body adjusting? Is this my body asking for support? Or should I be getting a divorce?"
"There's no amount of hormones you can pump your body full of that's going to make your libido crank up if you're not into it."
"We are patient zero. We are figuring this out for ourselves."

A 2022 dating survey showed that a whopping 69% of American men say that fear of being labeled "creepy" impacts how they interact with women. And 44% said it diminishes how much they interact with women at all, romantically or otherwise.
In other words, the fear of being creepy can hold you back from all connection with women, not just in the realm of dating/relationships.
But let's talk about sex and dating for a moment. The cruel irony is that this kind of fear usually means you've got a good heart — but left unchecked, it can make you shrink, go invisible, and tuck your sexuality away entirely ... which kills polarity.
Here, Jason and I count down the top 3 ways to make sure you're NOT coming off as creepy. We get practical as well as emotional. I share the "library story" I still think about; Jason gets honest about the years he spent frozen and numb — and we get into why whoever is breathing more deeply in the room ... is holding alpha.
We also share the simple thing you can say out loud that turns an awkward, high-stakes context with a woman into one where she actually feels safe enough to say yes — including the exact line that helped one man ask out a longtime friend and land in the healthiest relationship either of them had ever had.
plus a breakthrough that took one client from scared-and-small to making out outside a restaurant with a woman he thought was "out of his league" — plus the married man who finally said six words to his wife he'd never dared say in their whole marriage, and how she responded.
Whether you've frozen, over-corrected, or held your fire because you were terrified of being "that guy" — single or married — this one's for you. You can move beyond creepy and reclaim this part of yourself ... and everyone benefits when you do.
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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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Memorable quotes from this episode:
"'Men are afraid women will laugh at them. Women are afraid men will kill them.'"
"There's an inverse relationship between safety and creepy."
"Head evokes head, heart evokes heart, body evokes body."
"And she said, 'It's not that I don't want that — it's not like this, right now.'"
"The problem isn't always the context — it's whether you set a container and can speak to it."
"There's nothing wrong with our sexuality. It's what we do with it."
"Whether you say yes or no, I'm going to be okay."
"'I find it really hot when you wear a short skirt and boots!'"
"Shame is healed in community."