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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 Be the Best Partner He Ever Had

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