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

How do you deal with mismatched libidos? It's one of the biggest issues couples face.

Ever lie in bed next to someone you’re deeply attracted to ... and talk yourself out of reaching for her? In one man’s words: “We’re married, and I can’t even touch you.”

When one partner wants sex (or cuddling, or affection) way more than the other, it can eat a relationship alive. The high-desire partner ends up desperate, ashamed of even having the need, and feeling rejected over and over.

The low-desire partner braces against every touch...

Ever feel like sex is less of a good time and more of a test you can’t afford to fail?

In the words of one man from my sex research: “I’m afraid of giving a bad performance and not being invited back.”

After coaching men for over a decade, I can tell you this is one of the most common things I hear behind closed doors -- and one of the least talked about. But overthinking about sex is extremely common. One review in Sexual Medicine Reviews says sexual performance anxiety affects up to 1 in...

Ever lie there afterward wondering what she’s really thinking? The romantic night is all set up -- the hotel, the champagne, the view -- and your d*ck doesn’t cooperate. Or it’s over in three minutes. Again.

Here, we back the curtain on what it’s actually like from HER side of the sheets. What have women internalized about how their sex appeal relates to his "performance"? My guest share about her 13-year past relationship where PE was never really discussed, as well as a deeply attuned current partner who did one simple thing early on...

First some stats on premature ejaculation, delayed ejaculation, and erectile dysfunction:

Ever feel like your body has stopped cooperating in the one place you most need it to? Or it's totally hit-or-miss -- in one man's words: "I never knew whether I was going to ejaculate at all. I had no control over it."

Erectile dysfunction (ED), premature ejaculation (PE), and/or delayed ejaculation (DE) can have a devastating impact on a man's sense of self-esteem, as well as on sexual satisfaction in relationships. And we don't talk about this enough. These issues come up in my sex research constantly, and are a daily reality for hundreds of...

“I know I’m a good guy - I’m kind and compassionate and caring … so why don't girls want me??”

This was one of Scott's main concerns in middle and high school. It felt like it was happening for everyone around him, but not him.

Fast forward a few decades and now he's got overflow in his love life -- he's married and experiences affection, sex, closeness, and emotional availability on the daily. So what changed?

Here we talk about the excruciating phone call in 6th grade that kicked everything off; the confusion...

Do you want women to feel deeply safe with you? Do you want your partner to feel not just satisfied physically and emotionally, but able to truly surrender with you -- let go of her inhibitions and experience IMMENSE PLEASURE on every level?

Then she needs to trust you.

Here we share our personal experiences of trust -- when a man has earned it and we've been able to really lean in ... and when we've been let down and felt the lack of trust.

The truth is that a woman must trust you...

“Who’s taking up space in the relationship?”

“If I don’t have any boundaries, I’ll often attract someone who doesn’t honor boundaries.”

“Partners like this can be really smart.”

“Because you’re the closest to them, you get all the wild crazy.”

“I hear a new rule, I try to do that, and I still lose.”

“It’s pretty hard to do alone.”

“It really feels like, ‘There is no way out.’”

“It can be comfortable but not very alive.”

“Our guys don’t just want sex...

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.

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 ho...

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...

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...

"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 an...

“I was nervous as hell.”

So shares one of the men in this episode about how he felt stepping onto the land of our in-person retreat. In another's words, “I went into a panic because I’m having flashbacks of summer camp.”

What's it really like to do live men's work?

The truth is, most men that come to live retreats are intimidated in one way or another. Rates of bullying are astronomically high, and you don't always know what to expect. As another put it, “There’s a shared understanding of the brutality betw...

Have you ever felt like your woman was routinely frustrated, resentful, or annoyed with you? Like you can't get anything right, and then on top of that, when it comes to sex or physical intimacy, FORGET about it. Not happening.

If so, you may be contending with reverse polarity. This can happen in either direction, but we find that with our clients, it's illuminating to explore the flavor when a man is more in omega (his feminine) and a woman more in her alpha (her masculine).

Here, we delve into the different stages of relationship...

Ever feel like you're doing everything "right" — showing up, being kind, respecting her — but only getting crumbs?

First dates that never turn into second dates. A marriage where you've quietly become roommates; no matter what you do, there's no sex, and there's not even very much affection. That feeling of putting in a ton of effort and still spinning your wheels.

If any of that lands, you're likely living out some version of Nice Guy Syndrome.

Outgrowing being a Nice Guy doesn't mean becoming a jerk. It does mean that you learn some skil...

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?

...

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...

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...

"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...

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 yo...

Who doesn't have trust issues? Let's be real.

Whether it shows up as "I don't trust her to handle my anger," or "I'm afraid I'll just be treated like an ATM" or, "I can't relax until I know the person really, really well," — almost all of carry some version of trust concerns into our dating and relationships.

Here, my dear friend and co-facilitator Violet Lange and I do something we don't often get to: We put our worlds side by side. I work primarily with men who are attracted to women; she works primarily with wo...

You love your partner. You're committed. But the sex has slowed to a trickle — once a month, once every six months, maybe not in years — and you're starting to wonder: "Is this just what long-term partnership is?"

No -- it doesn't have to be. Unfortunately, if this is happening and you're feeling lonely in your marriage, you're not alone. And it can be hard to know what to do; millions of men feel ill-equipped to address the issue because either a) whenever they do, it becomes a fight; or b) they're scared of coming off as demanding or a...

Ever been told you're a "great guy!" but she's "just not feeling it"? Or felt like you're endlessly chasing women but never being pursued yourself?

Here, we dig into what's actually happening when women consistently report not feeling attracted to you -- and what you can do about it.

The truth is, attraction only has a little to do with what you look like physically. For example, one client came into our program good-looking by every conventional standard: broad shoulders, nice body, the whole thing.

But he wasn't having success with women. He...

You know the feeling. You've been holding a vision — for the partner, the family, the sex life you actually want — for months. Maybe years. Maybe decades. And it's still not here.

And underneath the longing, there's a quieter, scarier question: Is there something wrong with me that it hasn't happened yet?

Here, my dear friend and co-facilitator Violet Lang and I have an honest conversation about what it actually takes to hold a long-term vision without collapsing or giving up. We speak vulnerably from experiences in our own lives, as well as the lives of hund...

She used to want it. Now she doesn't. And you're not sure if it's you, the kids, the stress — or something that's quietly shifted inside her.

A lot of the time, it's her hormones. Specifically, perimenopause or menopause.

Here's what most people don't know: perimenopause doesn't start at 45 years old. Dr. Debra Durst — an MD who left traditional medicine to specialize in hormone optimization and sexual wellness — is seeing it in women in their 30s, and sometimes even their 20s.

And the first hormones to drop aren't estrogen -- they're progesterone and testosterone. Which...

It’s one of the top questions in Dr. Kelly’s men’s health practice. 

And it’s not just coming from older men — it’s guys in their 20s and 30s. We're talking 27-year-old chiseled Marine sergeants walking in saying, "I can't get motivated. I rarely wake up with erections anymore. I haven't had sex with my girlfriend in two weeks." And their buddies are reporting the same thing.

It's not all in their heads, either. According to Dr. Kelly, the average 22-year-old man today often has the testosterone of a 70-year-old. 

And get this...

You know the moment. She comes at you with heat — frustrated, hurt, disappointed, or just a lot — and something inside you freezes.

Maybe you start minimizing her experience ("It's not that bad"; "You're exaggerating"). Or you lawyer up ("Well but you also said ____" or "That's not what I meant; if you'd just listen while I explained..."). Or you look present, but you're not.

It's one of the most common patterns we see in hetero relationships. And the story we've been told about why it happens is mostly wrong.

Here, Jason and I dig into...

Has it always been clear to you where you fit into the world? -- what your purpose is, what you contribute, what your "worth" or "value" is, as a man.

If so, you're in the minority these days.

A modern young man has no official initiation into adulthood -- no rite of passage. So he often ends up "adrift on a sea of shame," as story weaver and healthy masculinity educator Djeli Celestia, puts it.

That line alone stopped me cold, because I've seen it so many times in the men I work...

Ever felt like there's something blocking you in love — something you can't quite name, but keeps showing up? Maybe you've got anxious, avoidant, or disorganized attachment traits, or you've sacrificed your needs for others or struggled to own your sexual attraction.

It's easy to feel like our issues in our sex or loves lives are all our fault, and all ours to fix. But what if something bigger is going on?

Here we explore one of the most fascinating -- and still somewhat underground -- healing modalities out there: Constellations (aka Family Constellations).

Co...

Globally, hundreds of millions of men contend with erectile dysfunction, premature ejaculation, and delayed ejaculation. One 2021 US national survey found an overall ED prevalence rate in men of around 24% — that’s nearly one in four.

But even in men’s work spaces (men’s groups, retreats, etc.), one rarely hears these topics discussed. Why?

In a word: shame.

Here, Luke and I debrief our recent course, Sexual Mastery, and what patterns we saw in terms of what it actually takes to heal sexual dysfunction — from ED to delayed ejaculation — in a lasting way.

Spoiler...

Do you ever wish you were more grounded, had stronger boundaries, felt more clear and aligned in your purpose, and could powerfully ask for what you want and need?

If so, then you might resonate with Nice Guy Synrdome, and you probably want stronger YANG energy (as opposed to YIN energy). Here, Luke breaks down the mind-body connection through the lens of traditional Chinese medicine (TCM). explaining how unspoken resentment, chronic worry, and swallowed boundaries don't just affect your relationships — they show up in your immune system, your gut, and your posture.

Meanwhile, we get re...

The kids are almost out of the house. And there's this quiet, low-grade dread that when they go … you'll both be left staring across the table at someone you believe you love but barely know anymore.

That dread is well-founded. Couples are 40% more likely to divorce after kids leave home. Divorce rates for Americans over 55 have doubled since 1990. And roughly half of all divorces now happen to couples who are 50+ — right in this window. The empty nest isn't just an emotional transition. It's a relationship reckoning.

But there's a surprising and uplifting twist here: research also...

Have you been through some sh*t? Or maybe you’re in it now.

If you feel stuck, or that there’s stagnant energy in your system that needs some unblocking, Breathwork can be a way of getting MOVING.

It can help you to finally let go.

Perhaps you’re not getting what you want in sex and intimacy, or maybe you just feel empty a lot of the time and don’t know what to do about it.

Or maybe you could write a PhD on your “issues” but you know you nee...

Ever felt obligated to "take the next step" in a relationship -- for example, becoming exclusive, moving in together, getting married, buying a house, having children, etc.?

Was it what you really wanted, or was it just what your partner or others thought you should be doing at that point?

Millions of people quietly make alternative life choices and relationship choices -- but we rarely talk about them. Enter Amy Gahran and her book, Stepping Off the Relationship Escalator.

In the world of sex, dating, and love relationships, the cultural norm is the "...

“A common pattern we see is that the sex has dried up.”

In millions of marriages around the globe, one partner is starving for intimacy, and the other feels confused, frightened, frozen, or all three. The sexually guarded partner doesn't know how to open, and their partner feels stuck, unhappy and alone.

So what can they do?

Here we explore exactly that, with a focus on a woman partner who may be terrified of engaging in sexual healing. We explore the origins and root causes of this pattern, as well as sexual intimacy, emot...

Have you ever felt like you've done everything right — therapy, journaling, the inner work — and yet you were still kind of... stuck? Like you intellectually understood your pain but couldn't actually move it?

That's where Sara found herself after a 10-year marriage ended; a year of talk therapy later, she still wasn't where she wanted to be. She felt alone in a battle with the voice inside her that said she was a failure, unlovable, and destined to repeat the past.

So she did something most people would never, ever do — and it changed everything.

I...

Ever been in a relationship where you felt like it started off GREAT, but over time it became really hard? Ever felt like you had electric sex with someone, especially at the beginning, but then you were often put in the doghouse for doing something “wrong,” and that eventually you ended up constantly walking on eggshells to try not to trigger your partner? Then you’ll likely resonate with this episode.

If you’re someone who struggles with setting healthy boundaries, you may have noticed a certain pattern in terms of the dating and relationship partners you’ve ended u...

Do you ever find yourself minimizing your own needs, and/or feeling responsible for others' emotions?

Do you tend to stay quiet to keep the peace, or freeze during conflict?

Have you ever struggled with boundaries or wondered why standing up for yourself feels so hard?

Here we explore a family dynamic that can be just as damaging for what doesn’t happen as for what does. If there was a volatile parent in your house and a more passive one (or if that's the dynamic you're in as a parent right now, wi...

“This is not something I ever thought I would do.”

So begins Kubir's story of moving from a spacious one-bedroom apartment in SF to Radish, a 13-person cohousing community in the East Bay.

“As I was getting older, my friends were getting partnered off,” he shared, and talked about his dating experiences before living in community as, in part, a way of experiencing companionship.

His is a unique perspective because he never thought he'd end up not only living in community, but dating while recently moving in, and having to answer questions to his new...