Exclusive | Kevin James admits dating is ‘tough’ as he doles out relationship advice Page Six
* This article was originally published here
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What It’s Like to Be a Guy
His name is Adam.
He’s 53. He’s 5’9”. He’s got greying hair. He’s in decent shape, but he’s not going to post shirtless photos on Instagram. He has a college education. He makes six figures but isn’t filthy rich. He has two kids and lives in the suburbs.
He’s probably a 7.
After taking time to heal post-divorce, Adam finally decided to put himself back out there. He posted his profile on Hinge. The results have been discouraging.
Adam swipes right on nearly 50% of women’s profiles, basically matching with anyone he finds remotely attractive. Yet the percentage of women who are open to meeting him seems disproportionately low.
While Adam considers himself a relatively cute, upper-middle class professional with a lot to offer, it feels like only 1 out of 10 women match with him.
So he does what any mildly neurotic adult does: he Googles and he discovers that this is normal: men like 46% of women’s profiles while women only like 14% of men.
Turns out, the top 10% of men get over half of all likes. And Adam, evidently, is not in the top 10%.
Not only that, but most of the women who do like him are not what he’s looking for. Adam isn’t searching for a fantasy. He’s searching for an equal. A peer. Someone with similar culture and values. Instead, he’s seeing women from random neighborhoods 30 miles away that he’s not attracted to.
When he does match with someone, the conversation invariably peters out. Either she has nothing in her profile, she responds with a series of one-line texts, she disappears for days at a time, or she vanishes without a trace, presumably to date a guy who is taller or richer. From this experience, Adam draws two conclusions:
1) Dating apps are terrible. Everyone’s on them, but the people he’s attracted to don’t swipe right on him, while the ones who swipe right on him feel like a total mismatch.
2) Women are shallow. When a cute, educated, upper-middle class divorcé can’t seem to get or keep anyone’s attention, something feels wrong with the world.
Adam didn’t have trouble dating in his 20’s when he was being judged for his looks and personality in real life. Online, it feels impossible to break through.
Even in the rare instance where he gets a first date, the women seem so guarded, skeptical, or burned out that it’s hard to make a real connection.
So Adam does even more research and discovers groups of other men who are having the exact same problems meeting women on the apps. The tone in those groups is bitter. Accusatory. They blame women for being unrealistic and materialistic.
Because, after all, if every woman is holding out for a 6’5” finance guy, what hope do normal guys have? To move to Thailand? To join Ukrainian dating apps? Or, more likely, to declare a strike on dating apps, women, and love, and focus on career and children?
Seems kind of sad, doesn’t it?
Here’s the twist: I deliberately gave Adam the same traits that I have.
When I was dating on Match 20 years ago, I enjoyed it. Even though I was 5’9” and didn’t make much money, I was good with words. Back then, that mattered.
Today, that facility with words doesn’t matter as much because dating apps are fueled by algorithms and checklists. And average guys like me would not make the cut.
Now, I’m not saying you need to shed any tears for Adam.
I’m saying that you and he have more in common than you think.
Both of you are decent, emotionally functional people trying to find love in a system that rewards the hottest, flashiest singles.
Both of you feel like the opposite sex is unfair and unrealistic.
And both of you are tempted to give up.
It would be a shame if you never met Adam because you deleted the apps, decided all men are terrible, or swiped left on every “7” who is currently being overlooked.
Because the truth is: most great relationships don’t come from “the top 1%.”
They come from someone who might not jump off the screen in 0.6 seconds, but shows up well when you actually give him a chance.
Which is why the goal isn’t to “win dating apps” and land the most impressive man.
The goal is to date smart so you can find a man who’s actually capable of taking care of you.
If you want real strategy, real feedback, and real results: book a call with me here.
You don’t need more swiping. You need a smarter plan and accountability to that plan.
Love,
Evan
Learn more about coaching with me
Book a breakthrough call with me
* This article was originally published here
Thursday, January 22, 2026
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Are You Sabotaging Your Own Love Life?
Strap yourself in for a story. It happens to be about a man but, as you’ll see, it can just as easily apply to you.
Mike is in his mid-fifties. He’s cute, charming, and successful. A self-made millionaire. Extremely well-read. Interesting to talk to at parties. Loves dogs, travel, and kids.
Mike also came from a broken home and could be classified as an avoidant attachment style. As a result, his dating patterns are generally the OPPOSITE of whatever I coach.
Looking for a long-distance relationship? Check.
Sleeping with someone quickly? Check.
Committing too quickly? Check.
Moving in before a year? Check.
Mistaking chemistry for compatibility? Check.
Trying to fix anxious, jealous, emotionally immature women? Check.
Staying in unhealthy relationships for months or years too long? Check.
We can go on, but you get the idea. This is a great person, who, despite his positive traits, makes questionable choices in love. When we talk, I think of my definition of happiness: Happiness is when your goals and your actions are aligned.
Mike’s deep-seated beliefs (based on his experience) and his refusal to let go of being a biological dad leads him to the same issues, again and again.
His belief that there are few good women in his city lead him to date long-distance.
Mike invariably finds a woman in another city or country with whom he has great chemistry, and they dive into a relationship. He often ignores the inconvenient fact that an LDR requires extensive travel and, eventually, moving her into his place within the first six months to accelerate things and keep the connection alive.
His belief that he must have his own children leads him to date 15-20 years younger.
Mike is Generation X and generally down about younger women, thinking that they’re too into social media, drinking, and their careers. If he needs a younger woman but generally doesn’t like younger women, well, you can probably see the problem.
The internal contradiction of what he finds attractive leaves him alone.
Mike values looks, intelligence and sophistication above all. He dates hot, brilliant, and accomplished women who often have anxious attachment styles, jealousy issues, and volatile communication methods. Even though he wants a nurturing career woman, he refuses to date single moms of any age, despite the fact that mothers are often nurturing.
My simple solution for Mike: let go of having kids, date an attractive, successful, single mom between 45-55 who is mature, financially independent, and family oriented. Be happy for the rest of your life because you found an equal partner who “gets you.”
Does he listen? Nope. He wants what he wants. We all do.
Now you may be reading this and shaking your head in frustration. Please don’t. If anything, I’d like you to consider how much you may have in common with him.
Do you have a belief that there are few good men in your city that allows you to dive into instant relationships with long-distance guys based on chemistry?
Do you have a fixed belief about the type of man you need to be with? College educated? Makes more money? Over 5’10”? Similar hobbies and interests?
Do you have internal contradictions that make love improbable? A gorgeous guy who only has eyes for you? A wealthy guy who is home by 6 and doesn’t travel all the time? A brilliant guy who has a high EQ, listens to you, and values your opinions as much as his own?
It’s easy to judge Mike for his refusal to compromise – and it’s easy for you to project what you think he should compromise on. But what will you compromise on?
If you’ve struggled to find a healthy relationship and you don’t know the answer, click here to talk to me. Sometimes, we’re too close to be able to see the answers in front of us.
Love,
Evan
Learn more about coaching with me
Book a breakthrough call with me
* This article was originally published here
Thursday, January 15, 2026
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The Gap Between What You Want and What You Need
You’ve put a lot of thought into why you’re still single. The answers are rote by now.
All the good ones are taken. Men don’t want women their own age. Dating apps are demoralizing. There’s no one attractive in your area. It’s hard to find someone at your level.
These limiting beliefs are all partially true, which is why it’s so easy to retreat to them. The problem, of course, is that SOMEONE is dating online successfully, SOMEONE is finding a man she respects in her city, SOMEONE is getting married this coming weekend.
And it’s not just women who are younger, thinner, or more impressive. It’s women like you. As a dating coach, I’m always looking for ideas that can give you an aha moment, jolt you out of your patterns, and get you to see your romantic situation through a different lens.
Which is why I got excited when I was walking my dog and listening to my friend, Rachel Greenwald get interviewed by my friend, Chip Conley on his Midlife Chrysalis Podcast.
Rachel is a high-end matchmaker who works primarily with successful men. Chip is the founder of Modern Elder Academy and was a guest on my podcast last year.
Anyway, Rachel was explaining her intake process, which is not dissimilar from my own. In it, she asks women to fill out a short questionnaire. One of the questions she asks is: “What are you looking for in a partner?” It sounds like a simple and benign question, and, indeed, for most women, it requires very little thought:
“Six feet tall, handsome, college educated, makes more money than I do, shares the same hobbies religion and politics, and has the same interest in family as I do.”
There are variations on this, of course, but you don’t have to be a dating coach to recognize that when you ask most women what they’re looking for, it’ll sound a lot like that. Naturally. That’s what you’re attracted to. That’s what you’ve been searching for online.
Then, a week later, when Rachel finally gets on Zoom with them, she asks a slightly different series of questions:
“Who makes you happiest when you’re with them? When you have a bad day and there’s only one person you turn to, who is that? Who brings out the best in you?”
The answer to this is often your Mom, your sister, or your best friend from college. Why? Because she accepts you. She doesn’t judge you. She sees you as the best version of you. You can relax around her. You can let down your guard around her. You can be yourself and never worry that she’s going to judge you or abandon you.
Once Rachel establishes the person who provides the most unconditional love, she goes back to the original list of what you’re looking for in a partner: height, weight, age, education, income, etc.
She points out that the gap between those two lists is what’s keeping you single.
The person who makes you happiest is the person who accepts you in full.
The person you’re trying to date is the person who impresses you the most.
It’s not about “settling” or giving up on traits you’re attracted to, but it’s DEFINITELY about paying closer attention to how your boyfriend makes you FEEL.
And if that sounds familiar, it’s because it’s just another way of arriving at the same conclusion that I’ve been talking about in this newsletter for years.
Now here’s the hard part:
There’s understanding what Rachel said and there’s LIVING it.
You’re smart. I know you understand that trying to date a man who is just like you (but better!) and doesn’t have any of your flaws is not realistic. I know you understand that just because you have chemistry doesn’t mean you’ll have long-term compatibility.
The real question is this: if you understand all of this, how come you’re still single?
THAT is the single biggest question most of my clients have.
THAT is what we answer together when I’m your coach.
It’s not just shining the light in your blind spots, it’s about giving you structure, action steps, and accountability while you’re dating, until you meet the right guy.
You’re never more dateable than when you’re feeling good about yourself outside of love. If you have a great life and no one to share it with, I’m excited to hear from you.
Love,
Evan
Learn more about coaching with me
Book a breakthrough call with me
* This article was originally published here
Thursday, January 8, 2026
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