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Friday, May 22, 2026

How to Learn to Trust Again

Two guys are hiking when they see a bear charging at them.

One drops his backpack and starts putting on running shoes.

The other says, “Are you crazy? You can’t outrun a bear.”

He says, “I don’t have to outrun the bear… I just have to outrun you.”

That’s what we’re going to be talking about today, using a real story of a real woman who is in a real relationship with a real smart, wealthy, relationship-oriented man. 

The moral of the story: you don’t have to be perfect—you just have to be the woman who makes a high-quality man feel like choosing you is the obvious decision.

Chelsea was referred to me by a matchmaker who charges $100-$500K for her services. The matchmaker said she wouldn’t take her on as a client until she worked with me for six months. The unstated implication was that Chelsea was cold, difficult, and a workaholic, and would therefore be hard to match with her stable of wealthy men.

I’m thrilled to say that – nearly a year later – none of those things are true. 

Chelsea is a multi-millionaire. She owns a small business with full-time employees, she has two kids and a live-in nanny. Her responsibilities are considerable. But all the stuff that the matchmaker was preparing me for has simply been a matter of a mistaken first impression.

Chelsea laughs easily. She asks me about my wife’s health. She’s open to feedback. She’s cried, multiple times, on our Zoom calls. Like many of my successful clients, she’s a Type A woman with a soft heart. She really is smarter and more productive than most men. She really does intimidate most men. Not because she’s trying but because she’s that impressive.

Two months ago, Chelsea started a relationship with a man who is truly her equal in terms of education, worldliness, and success. Like all men, he comes with a measure of baggage – but the baggage hasn’t proven to be that heavy. He’s a little older than she’d like. He’s got a little bit of that fragile male ego that needs stoking. But otherwise, Chelsea has been incredibly happy to find a man on her level. He’s been doing all of the initiating and planning, and eagerly took down his profile to focus on their relationship. 

There was only one problem – which came up on the phone this week. Chelsea is concerned that her boyfriend is still in love with his ex. Her evidence: she cheated on him less than a year ago, precipitating their divorce, and any mention of her still gets him agitated. 

And everyone knows that if a man still expresses emotion about his ex, that must mean he’s in love with her. Right? 

Not quite.

Being a good partner largely involves putting yourself in someone else’s shoes and considering why a good man would think/act differently than you’d want them to. 

When we perform this exercise on Chelsea’s boyfriend, it’s clear that he’s angry at his ex for many reasons: for cheating, for lying about cheating, for precipitating the dissolution of their former life, and for trying to get as much money as she can in the settlement. 

Could you blame him?

On our call, Chelsea said she was inclined to tell her new boyfriend to ignore his ex and stop talking about her. Perhaps they could move on without ever bringing her up again. 

That’s not how people work, I told Chelsea. Imagine if one of your friends had been cheated on by her husband, he initiated a divorce, and wanted to screw her financially.

Would you tell her to get over it? Would you tell her that she’s being thin-skinned? Would you tell her that she should stop talking about the central drama in her life?

You would not. Women never talk that way to each other. They lead with empathy. 

“Oh my God. He is SUCH a jerk. I can’t believe he did that to you. How selfish! How ungrateful! I’m so sorry you’re going through this. What can I do to make it better? Do you want me to kill him? Or just take you out for a nice meal? Whatever you need.”

This is what your friend wants to hear. You certainly would not be dismissive of her feelings, no matter how much she talks about her evil ex.

When I said this to Chelsea, her face lit up like a Christmas tree. 

In that moment, she understood that she needed to treat her boyfriend the way she treated her best girl friends. And she realized that she DIDN’T do this in her marriage. 

She’s not alone.

Janice’s husband of 26 years cheated on her and left her for a younger woman.

This devastating breach of trust ended a marriage that Janice acknowledges should have ended long before. Even though she’s happier now that she’s not stuck in a suffocating relationship, Janice has been scarred by her experience. 

Questions abound: How long was he lying to me? Was our entire relationship a lie? Was he in love with her? Was it partially my fault? Did I miss the signs? Could I have done anything differently? Will I ever trust again? Will I ever love again? How can I make sure this never happens again?

As her coach, it’s my job to answer all of Janice’s questions with sensitivity. Six months after hiring me, Janice is in a promising new relationship for the first time since her divorce. 

His name is Tom. Like Janice, he’s in his mid-60s. Like Janice, he’s fit and into personal growth. Like Janice, he was burned by a bad marriage but aspires to having a healthy one.

Four weeks into their relationship, Tom had already made clear that he wanted to be exclusive to Janice. He was even there for her when she got notification of a health scare.

In her words: “This morning when I woke up, I texted him at 7:00.  He didn’t respond right away because he was in the shower. When he did respond, he apologized for the delay and immediately called to see if I was okay.  I told him I could really use some support–thinking through options for my care. He was over within an hour. Said he would listen without giving advice unless I specifically asked for it. He is wonderful.

Asking for help was a very vulnerable thing for me. I didn’t even ask my husband all those years because of early experiences with him around it.  I understand now that he didn’t have the capacity.

All of this is to say how much I appreciate you and your work.  Without it I wouldn’t be where I am and for sure would have written off this great guy.  So yes I did the work…your work.  

Forever grateful,

Janice

Beautiful. Another Love U Love Story, right? Not quite. 

Two weeks later, Janice heard from a friend that Tom’s profile was still live on Match – even though he said he had taken it down. Janice left him a voice mail immediately, shocked because he never gave her any reason to question him. Here is his follow up text:

“Closing the loop. All notifications turned off and profile hidden, I am sorry that you have been given reason to question or doubt me. In my mind, I believe we are in an exclusive (monogamous) girlfriend and boyfriend relationship with the intent to build a long term relationship. I feel strongly that our ability to communicate is one of the things that has made this even possible. I don’t know the future but I do know that I am ready, willing and able to give this everything I’ve got to see where we can take this experiment together! Hope that helps.”

This exchange triggered Janice. She concluded her new boyfriend is dishonest, her trust has been broken, and she can’t continue. Before acting, she wanted to run it by me first. 

I cited a few core Love U ideas:

Look at his pattern of behavior. Tom wanted to be Janice’s boyfriend well before she was ready to commit to him. He has already stepped up to act like her boyfriend after her scary diagnosis. He immediately took down his profile and spent close to two hours explaining himself after this misunderstanding. Logically, it doesn’t make much sense for a guy to do all this…while actively pursuing other women. 

Remember: It’s full trust or no trust. This is not to say that every man is trustworthy – only that if you’re dating a man you don’t trust, you should get rid of him. “So”, I asked Janice, “based on your interactions thus far, do you trust him or not?” Turns out, Janice trusts him, despite the fact that his profile was still active. And yet she was this close to breaking up with him out of fear. 

I then shared a story about myself (as I am wont to do). 

See, although I met my wife at a party in Beverly Hills 20 years ago, we were both on Match at the time. After 4 weeks of dating, I pulled my profile down and started referring to her as my girlfriend. By our second month together, I’d already met her family, helped her move, and was planning a vacation to Greece and Turkey. 

And yet I remember distinctly in Month 3 of our relationship, wandering around her one-bedroom apartment, looking at everything on the walls and countertops as she finished up her shower. There were tons of artifacts from her international travels… and a wide-open laptop with an inbox showing dozens of emails from Match. 

Wait, what? This was my GIRLFRIEND. The one I was taking to Europe. My profile was down. I only assumed her profile was down. What could this possibly mean?

Given that my girlfriend was a high-integrity, high-EQ person, the most logical explanation was this: she just forgot to hide her Match profile. As a result, Match would send her an email with a bunch of hot guys every day that she would summarily ignore. 

Since my wife now has over 50,000 unopened emails in her inbox, maybe her profile is STILL up. I have no idea. All I know is that – because I trusted her – my mind didn’t immediately leap to the worst case scenario, but rather, the best case scenario.

This is what experts mean about “assuming positive intent.” When you’re with a good person, you should assume the most charitable interpretation of events until proven otherwise. This method has served me incredibly well throughout my life. 

I predict it will serve Janice well in her relationship with Tom.

Love,

Evan



* This article was originally published here

Saturday, May 16, 2026

How to Be the Best Partner He Ever Had

Two guys are hiking when they see a bear charging at them.

One drops his backpack and starts putting on running shoes.

The other says, “Are you crazy? You can’t outrun a bear.”

He says, “I don’t have to outrun the bear… I just have to outrun you.”

That’s what we’re going to be talking about today, using a real story of a real woman who is in a real relationship with a real smart, wealthy, relationship-oriented man. 

The moral of the story: you don’t have to be perfect—you just have to be the woman who makes a high-quality man feel like choosing you is the obvious decision.

Chelsea was referred to me by a matchmaker who charges $100-$500K for her services. The matchmaker said she wouldn’t take her on as a client until she worked with me for six months. The unstated implication was that Chelsea was cold, difficult, and a workaholic, and would therefore be hard to match with her stable of wealthy men.

I’m thrilled to say that – nearly a year later – none of those things are true. 

Chelsea is a multi-millionaire. She owns a small business with full-time employees, she has two kids and a live-in nanny. Her responsibilities are considerable. But all the stuff that the matchmaker was preparing me for has simply been a matter of a mistaken first impression.

Chelsea laughs easily. She asks me about my wife’s health. She’s open to feedback. She’s cried, multiple times, on our Zoom calls. Like many of my successful clients, she’s a Type A woman with a soft heart. She really is smarter and more productive than most men. She really does intimidate most men. Not because she’s trying but because she’s that impressive.

Two months ago, Chelsea started a relationship with a man who is truly her equal in terms of education, worldliness, and success. Like all men, he comes with a measure of baggage – but the baggage hasn’t proven to be that heavy. He’s a little older than she’d like. He’s got a little bit of that fragile male ego that needs stoking. But otherwise, Chelsea has been incredibly happy to find a man on her level. He’s been doing all of the initiating and planning, and eagerly took down his profile to focus on their relationship. 

There was only one problem – which came up on the phone this week. Chelsea is concerned that her boyfriend is still in love with his ex. Her evidence: she cheated on him less than a year ago, precipitating their divorce, and any mention of her still gets him agitated. 

And everyone knows that if a man still expresses emotion about his ex, that must mean he’s in love with her. Right? 

Not quite.

Being a good partner largely involves putting yourself in someone else’s shoes and considering why a good man would think/act differently than you’d want them to. 

When we perform this exercise on Chelsea’s boyfriend, it’s clear that he’s angry at his ex for many reasons: for cheating, for lying about cheating, for precipitating the dissolution of their former life, and for trying to get as much money as she can in the settlement. 

Could you blame him?

On our call, Chelsea said she was inclined to tell her new boyfriend to ignore his ex and stop talking about her. Perhaps they could move on without ever bringing her up again. 

That’s not how people work, I told Chelsea. Imagine if one of your friends had been cheated on by her husband, he initiated a divorce, and wanted to screw her financially.

Would you tell her to get over it? Would you tell her that she’s being thin-skinned? Would you tell her that she should stop talking about the central drama in her life?

You would not. Women never talk that way to each other. They lead with empathy. 

“Oh my God. He is SUCH a jerk. I can’t believe he did that to you. How selfish! How ungrateful! I’m so sorry you’re going through this. What can I do to make it better? Do you want me to kill him? Or just take you out for a nice meal? Whatever you need.”

This is what your friend wants to hear. You certainly would not be dismissive of her feelings, no matter how much she talks about her evil ex.

When I said this to Chelsea, her face lit up like a Christmas tree. 

In that moment, she understood that she needed to treat her boyfriend the way she treated her best girl friends. And she realized that she DIDN’T do this in her marriage. 

She’s not alone.

We all tend to be less empathetic to our partners than we are to our friends, employees, and strangers. This presents an incredible opportunity to change the narrative.

Without knowing anything about Chelsea’s boyfriend’s marriage, my guess is that if infidelity was involved, the marriage had been dying for years. 

Chances are that both parties stopped leading with kindness and were increasingly cold and dismissive of each others’ needs.

If that’s the case, wouldn’t it make sense for Chelsea to do the opposite? To kill him with kindness? To nurture him in a way that his ex likely did not? 

It seems obvious that patience, warmth, and trust will bring out a better side in this guy than doubling down on the criticism that his wife surely leveled at him in the past.

This is what I meant by saying you don’t have to outrun the bear. 

You just have to outrun his ex. How? By making him feel more accepted and appreciated than she did. I promise you: the bar is not that high. 

Love,
Evan



* This article was originally published here

How to Learn to Trust Again

Two guys are hiking when they see a bear charging at them. One drops his backpack and s...