By Chris Seiter

Published on January 18th, 2022

This is a complete breakdown of the times that a man will realize he’s lost a good woman.

So, if you’re looking to understand,

Exactly what makes men “regret” after a breakup.

The psychology of what happens when they realize they’ve lost you. 

Then you’re going to love everything I talk about in this guide.

Let’s get started.

  1. Men usually feel regret with missed opportunities
  2. He sees you on dates with other people
  3. He actually dates other people
  4. Combining the zeigarnik effect with the peak end rule
  5. The no contact grief cycle

Time #1: Men Usually Feel Regret With Missed Opportunities After A Breakup

Really when you’re looking at understanding the psychology of when a man realizes he’s lost a good woman you’re technically asking about the psychology of regret. After all, regret is the hidden thing underneath the surface that makes a man feel like he’s lost something.

Consider his breakup with you.

No one goes into a breakup thinking,

“I think I’m making a mistake.”

It’s only after they move on from you that they actually sit back and think,

“Huh…. I might have made a mistake.”

But there’s an opportunity cost aspect to this that most people try to ignore.

Opportunity Cost: Refers to the value a person could have received but passed up in pursuit of another option.

So, to put this in terms that make sense for your situation. In order for your ex boyfriend to feel like “he missed out” he needs to actually look back with an opportunity cost mindset and think he made a mistake in breaking up with you.

This begs an interesting question.

How do you stack the odds in your favor?

Essentially the only thing you can do is make him regret his decision by building yourself up into the highest value person you can become. It’s a very stoic mindset.

Indulge me for a moment. I’ve been very into researching the stoic philosophies lately. Specifically the greatest stoic (in my opinion) Marcus Aurelius.

What’s fascinating about Mr. Aurelius is that many of the greatest stoic quotes are attributed to him,

The happiness of your life depends on the quality of your thoughts.

Here’s another,

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You have power over your own mind – not outside events. Realize this, and you will find strength.

They come from his manuscript called “Meditations” which is one of the most widely renowned books in the world.

What’s really fascinating about this “book” is that it was never intended to be read by the public. Marcus Aurelius wrote it to himself as a kind of conversation and so it reads almost like a constant reminder not to go insane.

It roughly numbers 100 pages and has some mind blowing things but they all really revolve around two simple concepts.

You should only care about what you have control over, your mind, body, intentions and will.


Your goal should always be “to be good.”

What does any of this have to do with making your ex feel like he’s made a mistake in leaving you. Well, take a page from Marcus Aurelius and spend all of your time maximizing your potential as a human being towards some goal greater than yourself.

In essence this is what I’m constantly preaching when I talk about concepts like balancing the holy trinity.

It seems so simple and yet I would argue it’s one of the most difficult things to do after a breakup because your mind is constantly trying to get you to focus on things outside of yourself.

Things you have no control over.

There’s a certain cause and effect to giving into those thoughts.

Generally you start obsessing about your ex and your ex notices and it re-affirms their decision that they were correct to break up with you.

Do the opposite of what everyone else does.

Become a stoic.

Time #2: He Sees You On Dates With Other People

My team and I have been blessed with hundreds of Success Stories in our tenure here at Ex Boyfriend Recovery. Starting in 2019 I decided that I was going to perform a kind of rolling test any time I interviewed a success story.

The test was simple, check your ego at the door and understand what factors really make a difference in having an ex come back.

Two big patterns emerged.

  1. The first was that many of our clients got their exes back the moment they stopped wanting to get their exes back (the irony, right?)
  2. The second was that many exes also came back when a man saw their ex girlfriend dating other people.

Perhaps no one embodied this ideal more that success story Jamie Cantrell.

What sets Jamie apart from most of the clients I’ve interviewed is she literally threw herself into going on dates with other people. Which might rub some people the wrong way but weirdly there is some research to back this up as an effective coping strategy.

According to Psychology Today,

New research shows rebound relationships are surprisingly healthy.

Recent evidence suggests, in fact, that people who dive into rebound relationships get over their ex-partner more quickly and feel more confident in their date-ability (Brumbaugh & Fraley, 2014).

We even sort of see this with attachment styles as well. I’ve long made the case that an avoidant ex won’t give themselves permission until they feel like you’ve moved on from them completely.

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Only then do they feel “safe enough” to miss you. One of the best ways to indicate your are “over” your ex is if you literally move on and start dating someone else.

Also there’s the whole childish aspect of someone coming in and experiencing the fulfillment of what was once yours raising the overall value of that thing. I’m not in any way suggesting that women are “things” but rather some men can get possessive of them in this way and take this stance.

But it’s a double edged sword as you’re about to find out.

Time #3: He Actually Dates Other People

The grass is greener syndrome has always been one of my favorite concepts because it’s literally rooted within the idea of opportunity cost.

Your ex breaks up with you because he thinks he can find someone to better fulfill his needs.

Sometimes that risk can pay off but a lot of times it doesn’t.

As human beings we have a tendency to grow complacent in a relationship and take it for granted. One of my favorite movies ever is one that stars Jack Nicholson called About Schmidt.

Specifically there’s one scene that I feel sums up the point I’m trying to make about human beings becoming complacent in relationships perfectly,

To sum it up the scene it’s a guy writing about his wife and all of the things that irritate him about her.

  • The way she gets the keys out of her purse
  • How she throws her money away on her ridiculous hobbies
  • She tosses out perfectly good food
  • Her obsession with trying new restaurants
  • The way she cuts him off when he tries to speak
  • You get the idea

So, you have this guy just talking about his wife like he hates her and then something unexpected happens, she passes away. All of a sudden all of those little quirks he hates he misses. I think it’s a perfect allegory for the grass is greener syndrome.

Also a perfect allegory for “be careful what you wish for.”

Sometimes it’s only through dating other people that your ex will truly recognize what he lost which is a weird way of looking at it considering it’s probably your worst nightmare. But remember what Marcus Aurelius said,

You have power over your own mind – not outside events. Realize this, and you will find strength.

I want that to become your mantra.

Time #4: Combining The Zeigarnik Effect With The Peak End Rule

Let’s talk about those precarious positions you might find yourself in where your ex boyfriend hasn’t moved on to anyone else and still seems super friendly with you. In other words, you are doing everything that you used to do as a couple except becoming physically intimate.

I like to call this being stuck in “limbo.”

Now, the trap most women fall into is that they try to crawl out of limbo by reminding their ex how good they used to be together.

Their instincts are right. One of the best ways to to make a man realize he lost a good woman is to show him the high points of your relationship.

The problem is most women TELL him the high points of a relationship.

Literally going up to your ex and saying,

“Do you remember how good we used to be?” 

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Isn’t going to work.

Luckily, we’ve found a method rooted in psychology that can get the job done for you.

Let’s talk a bit about the peak end rule.

The Peak End Rule: The tendency for people to judge an experience largely based on how they felt at its peak and at its end.

Essentially human beings aren’t the greatest at remembering experiences as a whole but they are really good at remembering the big positive moments and the big negative moments.

For a breakup there’s an immediate rush to remember how you felt at the end of the relationship (which ultimately led to its demise) and the unfortunate mistake that I see most women making is they are doing things post breakup to reinforce that end.

Generally giving into anxious behaviors like,

  • Begging
  • Pleading
  • Stalking
  • Jealousy
  • Etc

As time goes on though (assuming they leave their exes alone) there’s a regression to the mean for their exes and they’ll start to remember the “high point” experiences. Especially if you factor in the avoidant mentality of feeling safe to miss an ex only after an ex has “moved on.”

But here’s my question.

What I’ve noticed is that it’s not necessarily enough to reinforce positive memories at the right time with ex. Rather, it’s much more effective to recreate those positive memories that they felt during the peak positive moments again with an ex.

The essence of the feeling they felt is what you are looking to replicate and to do that you are going to need to utilize another psychological principle.

The zeigarnik effect states that human beings are a lot more likely to remember interrupted or incomplete tasks better than completed ones.

It’s the same principle behind how television shows work. They try to end every episode on a cliffhanger so you’ll continue watching. After all, you need to find out what happens next.

So, going back to the peak end rule. When you distill it down and look at the natural flow of a conversation there’s a peak end aspect to it. For reference I’ve charted what a natural conversation on the phone looks like between two people who like each other.

Notice those arrows?

Those are considered the high points of the conversation or rather the “peak” of the conversation. If our goal is to bring your ex back to those feelings he felt during the peak moments in your relationship then one of the most clever ways you can do this is to literally utilize the zeigarnik effect around the peak moment of conversation.

What would happen if you suddenly ended a conversation around the peak moment?

Well, you’ll reinforce the feeling he felt and he’ll be left remembering that feeling. It’s not like you’ll get him back right away but an interesting thing will happen. If you consistently get in the pattern of doing this you’re going to stand apart from the crowd and you’ll notice he starts reaching out to you first.

Time #5: The No Contact Grief Cycle

You didn’t think I was going to go an entire article without talking about the no contact rule did you?

One of the moderators of our private Facebook support group wrote this amazing post (within the group) on the importance of the no contact rule where she broke it down so that you could understand the science of it.

I highlighted the relevant portion we are going to be talking about in this article today.

Let’s assume you decide to do a no contact rule on your ex for a minimum of 30 days. No matter what circumstance you find yourself doing some form of no contact is usually a good idea because it’ll help you NOT reinforce the decisions that your ex broke up with you in the first place for.

As you implement the no contact rule on your ex they are going to be going through the typical five stages of grief.

  1. Denial
  2. Anger
  3. Bargaining
  4. Depression/Regret
  5. Acceptance

The depression/regret phase can occur approximately at around the 3 week mark of the no contact rule. Of course, according to our moderator this model is not linear. Every ex is unique and depending on their attachment style they may feel regret around the 6 week mark.

But they will at least consider it at some point if you give them enough space to consider it.


Desire is created within space. Without it your ex won’t desire you and they won’t feel like they made a mistake.

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3 thoughts on “Times When A Man Realizes He’s Lost A Good Woman”

  1. Elena

    February 7, 2022 at 5:13 am

    I was in a long distance “unofficial” relationship, but decided my partner did not give me the peace and sense of security I needed; I felt like everything depended on his mood and he was never really open with me. So, after a couple of years of an on and off kind of thing, I finally left.
    It’s been over a year since I said to him I couldn’t stay with him anymore and some months after, I found someone who respects me and makes me feel loved and cared for.
    However, my ex partner has been trying to win my attention through social media (he tried to get back with me with loving messages, he tried to respond to every IG story, he constantly tweeted about how much he wanted me back). I’ve erased him from most of my social media but I’ve seen through friends even a year later that he just can’t let go and keeps on posting things about me and how much he desires to get me back.
    What do I have to do? I feel so uncomfortable thinking this person is wasting his life because he cannot get over me.

  2. Meryl

    January 20, 2022 at 10:20 pm

    Hi there, my ex broke up with me over a month ago saying his mental health wasn’t at a good place for the relationship. We didn’t talk for 20 days but then we exchanged our stuff and during that time we started talking about the relationship and I told him I wish he hadn’t given up on us and he got really mad and then blocked me on Facebook saying that he never wanted to talk to me again. I’ve been mainly focusing on myself and decided to no contact for 45 days, but he is so so mad at me and having friends pass rude messages. He used to be so kind and sweet in our 7 mo relationship, what happened? I don’t know if I want to get back together but I do at least want to be friends, but will that be possible with this situation? Especially if there is mental health/anxiety issues on his side?

    1. EBR Team Member: Shaunna

      January 30, 2022 at 9:25 pm

      Hi Meryl, your exes behaviour seems a bit extreme especially when your break up sounded civil. If he is really struggling then he is going to need time to work and focus on himself to feel better but that does not mean that there is no way back I would suggest that you avoid speaking to your friends about him going forward if you do want to get back together.