When One Early Dating Mistake Feels Like It Cost You Everything
Matthew Hussey
Relationship coach Matthew Hussey addresses a familiar kind of regret: the belief that a single slip-up in the first weeks of dating destroyed a connection that could have been special. Using a story about a man named John, Hussey argues that the mistake usually matters less than the story we attach to it. The idea that it "would have worked" is mostly projection, the panic it causes points to scarcity in the rest of one's love life, and any attempt at repair works better when it comes from calm rather than reactivity.
The Story of John and Sarah
Hussey opens with a setup that looks like it's heading for a fairy-tale ending, then drops it. The book he's holding, he admits, is "nothing but a prop," and he tells what "really happened."
Three years earlier, John went through a terrible breakup in which he struggled to state his needs, set boundaries, or speak up for himself. He vowed never to be that person again. He spent the next three years working on his communication skills and attachment style through videos, podcasts, books, Hussey's programs, and a retreat.
Then he met a woman, Sarah, in his yoga class. Their first coffee lasted five hours and turned into dinner. She was warm and receptive and clearly liked him. After two great dates and plenty of texting, she went quiet. On a Saturday afternoon John texted suggesting they try a new coffee shop, and he heard nothing until Sunday evening.
The silence triggered him. He remembered all the times in his previous relationship when he hadn't spoken up, right before he learned his ex had cheated on him. Determined to assert himself this time, he sent: "If you didn't want to see me again, fine, but ghosting is very cowardly." Afterward he felt proud. He hadn't bottled up his feelings, he had prioritized himself and spoken his truth, and it felt as if three years of work had paid off.
Then Sarah replied. Her dog had died the day before, she had been upset all weekend, and she had planned to get back to him later. His text had made her feel worse. She asked him not to message her again and told him to take care.
Only in hindsight did John see that he had overreacted to one unanswered text from someone he'd seen twice. He should have asked what was wrong before drawing a boundary, or at least waited longer. He felt he had lost a rare connection, the kind that seems so hard to find in the age of dating apps. An apology felt impossible, because messaging her would violate her request not to. So John began to dwell.
Why Early Mistakes Feel So Unforgivable
Hussey says many people feel that early dating demands near-perfectionism, with no room for small errors: "One small blip and you are gone." He identifies what makes early situations different. Sarah didn't know John well enough to know his other qualities, such as the fact that, had he known about her dog, he would have brought flowers and supported her through her grief. With no established connection, she had no reason to read his sharp text as a bad day or old wounds flaring up. In Hussey's words, John "was not a three-dimensional character to her yet."
He goes further and suggests that Sarah's response wasn't necessarily a verdict on John or his one text. In his reading, she shut the door based on past experiences with aggressive men and assumed John was the same. She had a history of ending things at the first sign of friction. John, meanwhile, sent his text because of his own history of not standing up for himself, and he overcorrected in the wrong situation, seeing Sarah through the lens of the ex who cheated on him. "Both John and Sarah reacted to their history, not to the person in front of them," Hussey says, and that is part of why such mistakes are so easy to replay.
First: Recognize the Projection
Hussey's first remedy turns the painful thought against itself. The catastrophic thought is that someone rejected you without really knowing you. But that same fact, he argues, can act as a pressure valve: if they didn't know you, you didn't know them either. Believing the two of you would have been right for each other if not for this one mistake is, he says, "an extraordinary act of projection about the rightness of this relationship."
That belief assumes nothing else would have gone wrong a week later, that there wouldn't have been a fight a year in that ended things, and that neither of you would have discovered something in the other's deeper character or personality that made you incompatible, something that had nothing to do with the mistake and everything to do with actual compatibility. His point is to let go of the idea that someone you've barely met, perhaps after only a couple of dates, was your perfect person except for this one mistake.
Second: Become Abundant Again
Hussey anticipates the objection: But I really did connect with this person. I never meet anyone I like, I hadn't in years, and this person seemed to like me back until that moment. How will I find that again? He calls this thinking a product of deep scarcity, the result of a love life that isn't producing enough opportunities to feel abundant.
The fix he proposes is to reinterpret the fear. Being scared you'll never meet anyone else doesn't prove this person was the right one. It means something has gone wrong in "the ecosystem of my love life": no new people are coming through, and there's no trust that anyone else will. Instead of asking how to fix things with this one person, he suggests asking how to fix the situation that makes this person feel like the only possible match. (Here Hussey promotes his free "Dating with Results" training as a way to create more opportunities.)
If Not Abundant, Then Defiant
For people who can't yet believe someone better is coming, Hussey offers a fallback: defiance. The reasoning is that if you're afraid you can't live without someone, that fear is itself a serious vulnerability, because no single person you're dating should hold the key to your happiness. So the defiant stance becomes: "If I can't live without them, I must live without them. If I can't lose them, I must be able to lose them," because nobody should have that much power over your life. At minimum, he says, the most important thing in that moment is to prove to yourself that you can lose this person and still be happy.
Third: Learn the Lesson, but Only Your Part of It
Hussey acknowledges that nobody wants to hear there's a lesson in a fresh mistake. In that moment we want the person back, or a time machine. But he argues the hurt is valuable, because when something truly stings, it gives us our best chance to change.
He then softens the point in two ways. First, if the projection point has landed, the loss may not be as serious as the brain insists. Second, mistakes usually involve both people's actions. John reacted out of fear of being ghosted. He was met by someone with her own avoidant tendencies, driven by fear of aggression. Sarah didn't say something like "that was unfair, my dog just died and I'm in a bad place," which would have given John a chance to apologize. She ended contact. Hussey calls this a "dance" between both people's natures or trained responses. With someone a little more gracious or slower to cut him off, John might have had a very different conversation. So the lesson, he says, is to own your part but not theirs. People often don't give enough weight to the other person's share in why things fell apart.
The Person as a Stepping Stone
Hussey also asks listeners to see the person as a stepping stone. If there are many people we could be happy with, the person we end up with will be someone we meet at the right stage of our own healing, and who understands that stage and makes room for who we are at that moment. From that angle, whether it could have worked with this particular person is "kind of irrelevant." The one it works with will be someone met in the right state at the right time on both sides. When that happens, he says, we'll look back and laugh at the idea that one mistake with one person ruined our happiness.
Fourth: Don't Reach Out From Reactivity
His final point is one word: reactivity. Many people want to repair things with someone they've lost, whether by telling them they were wrong to leave or by trying to sell them on trying again. Hussey says the worst approach is one driven by anxiety, stress, scarcity, and fear. When someone senses that reactivity, they sense a need for a particular outcome and an attempt to manipulate the situation to get it.
He contrasts two possible messages to Sarah. The reactive version pleads: I'm so sorry, please don't give up on this, I think we have something special, I have strong feelings for you. The version he recommends apologizes for misjudging the situation and coming from a reactive place, acknowledges he didn't mean to add pain to what must already be a terrible week, expresses sympathy about her dog, offers to listen if she wants to talk, says it would be nice to hear from her again, and wishes her well in her grief.
That message, Hussey says, isn't trying to get a result today. It plants a thought that may "detonate" over time. After a few bad dates, or feeling lonely, or noticing she doesn't connect with others the way she did with John, Sarah might think she oversimplified or underestimated him. He suggests the dynamic can flip: the more she reflects on how John handled his mistake, the more she may wonder what potential she lost, and she might be the one to text or call. He presents this as a possibility, not a guarantee.
Hussey ends with a caveat. If you're still too reactive to trust what you'd say right now, the first step is to regulate your emotions, and only then think about what to say calmly and from a sense of abundance. He points to his own AI tool at askmh.com as one way to do this.
What's this? A video that begins in the book nook. Well, it must be your lucky day. Our story today may be one you relate to. It's about a man named John. Let me know in the comments if you do.
John went through a terrible breakup 3 years ago during which he struggled to state his needs, draw boundaries, and speak up for himself. He told himself he would never be that guy again and spent the next 3 years working on himself, his communication skills, and his attachment style. He watched all of the videos, listened to the podcasts, read all the books, watched all my programs, came to my retreat.
And then he met a beautiful woman at a yoga class. They went for coffee, one thing led to another, and John and Sarah lived happily ever after.
That's not how the story ended, is it? Because John isn't in this book. This book is nothing but a prop. Here's what really happened. One day John met a woman in his yoga class. They went for coffee, it lasted 5 hours, it turned into dinner. She was receptive, warm, she liked John. But after two great dates and tons of texts in between, Sarah went quiet. John messaged her on a Saturday afternoon saying, "We should try that new coffee shop if you're down," and then didn't hear from her until Sunday evening.
He got triggered. He suddenly remembered all of those times in his previous relationship that he hadn't spoken up right before he learned that his ex had cheated on him. So he decided this time he would assert his boundaries, and he fired off a text message: "If you didn't want to see me again, fine, but ghosting is very cowardly."
After sending the text, John felt proud of himself. He didn't bottle up his feelings like he had in prior relationships, he prioritized himself, and he spoke his truth. All the work he had been doing on himself for 3 years paid off and it felt great until he got Sarah's response.
"Hey, my dog died yesterday and I've been really upset this weekend. I was going to get back to you later. Your text made me more upset. Please don't message again and take care."
It was only in hindsight that John realized he had overreacted to one missed text with a woman he had only seen twice. That he should have asked what was wrong before drawing the boundary or at least waited longer for her response. He realized how quickly he lost a great connection, a connection that seemed so hard to find in the age of dating apps. He realized an apology wasn't feasible because messaging her again would cross her "please don't message me again" boundary. And so began John's dwelling.
In case you are just learning this fact, I'm Matthew Hussey. I've been a relationship coach for nearly 20 years. Subscribe and like this video and let's get started by breaking this situation down in the analysis chamber. Before we get into the analysis, let me just start by doing some things that people with glasses do.
I don't need these for analysis. I don't even wear glasses, but a man can dream. Anyway, if you are someone who has been dwelling about an early dating mistake in which you believe that you sabotaged something with someone very potentially special, you are not alone. It feels like getting people to invest and get to know you in the early stages takes an unbelievable amount of perfectionism with no room for error or small slip-ups. One small blip and you are gone.
There is one key thing that makes early dating situations unique. Sarah did not know John well enough to know about all of his other great qualities, that he's the type of guy who, if he knew Sarah's dog had died, would bring her flowers and support her through her grief. There hadn't been an established connection for her to excuse his sharp text as John just having a bad day or getting triggered by a bunch of historic wounds. John was not a three-dimensional character to her yet.
In fact, Sarah slammed the door shut based on her prior experiences with men who were aggressive and decided that John must have been the same. Slamming the door shut wasn't necessarily a reflection of John's one text or even necessarily a rejection of John. It was about Sarah's own patterns and having a history of shutting things down at the first sign of friction. John sent the text he sent because of his prior experiences of not standing up for himself and overcorrecting in the wrong situation, seeing Sarah through the same lens he saw his ex who had cheated on him.
Both John and Sarah reacted to their history, not to the person in front of them. That is what can make early dating mistakes so easy to dwell on. So, in these situations, here is how to overcome the constant replaying of events in your mind.
We have to recognize that while our catastrophic thought is that in early dating someone has rejected me without really knowing me based on a mistake we've made, that same thought can actually be the pressure valve to this whole situation because it makes us realize that the idea that we would have been right for this person and they right for us had we not made this one mistake is an extraordinary act of projection about the rightness of this relationship.
It assumes that there wouldn't have just been something else a week later that meant that one of you decided the other one wasn't right. It assumes that there wouldn't have been a fight that you would have a year into the relationship that meant the relationship didn't work. Or that you didn't see something in each other's deeper character or just the way that you are in your personalities that made you incompatible that had nothing to do with the mistake that you could change. It had everything to do with how compatible you actually were. We have to get out of this idea that this person we barely know, who we've only been on a couple of dates with, if that, was our perfect person had we not made this mistake.
Now, look, you may be thinking, "Yeah, but I did have a great connection with this person. I never meet anyone great and I haven't met anyone I really liked in years and then I met someone who I didn't just like, they seemed to like me back until this one moment. And how am I going to find that again?" That is all coming from a place of deep scarcity because right now my love life is not creating the kind of opportunities that are making me feel abundant.
So, the second thing we have to do: become abundant again in our love lives. We have to have an abundant mindset that says, "This is not the only person in the world." We are getting trapped in this idea that we just screwed it up with the only one we had. We have to start saying, "If I am scared that I'll never meet anyone else again, that doesn't mean that person was the right person. That means that there is something that's gone wrong in the ecosystem of my love life. That means there are no new people coming through. I have no trust that I'm going to meet anyone else." Instead of "How do I remedy it with this person?" saying, "How do I remedy the situation in my life that means there are so few people coming through that I feel like this is the only person I could have made it work with?"
And by the way, if you are listening to this going, "But Matthew, I literally do not create opportunities in my love life. It feels like there are so few opportunities for anything real to come along," I have a training for that. It is called Dating With Results. It'll take you 90 minutes to watch. It's completely free. I've had over a million people come through it, and it will literally show you how to multiply the opportunities in your love life so that never again do you get fixated on one person being the only good option for your love life. This is one of the things that helps us move on. I will leave a link below. It is datingwithresults.com. Go watch that after this video if you want more options in your love life.
If you can't become abundant yet, become defiant. Defiance says, "If I'm scared that I can't live without someone, then I must. If I'm scared that my whole life, my happiness depended on this one person, then that's an enormous vulnerability in my life. I can't exist with that kind of vulnerability that says that this person I'm dating is the key to my happiness. If I can't live without them, I must live without them. If I can't lose them, I must be able to lose them because no one, no one can have that amount of power in my life."
If you can't become abundant, if you can't believe that someone better is coming right now, if you can't believe that another option is on its way, at the very least have the defiance that says, "If I'm scared I can't lose that person, then it's the most important thing in the world right now to show myself that I can lose this person and still be happy."
Now look, this next part is a part that none of us like hearing, but I'm going to put a twist on it that is going to make it something you want to hear. In these situations where we make a mistake, especially if it really was our mistake, we take the time to learn what we can. None of us want to hear this because in the moment where we make a mistake, we don't want to be told there's a great lesson in here. We don't want it to be a growth moment. We want the person that we just sabotaged it with. We want to have a time traveling device that allows us to go back and undo that mistake because it hurts.
But the hurt is actually valuable. And the reason it's valuable is this. When something genuinely stings, that is our best shot at changing something for ourselves. Now before you hear that and you think, "This point sucks because it just means that I've got to turn this into a learning lesson for myself. It means that there is a part of it that I genuinely need to own and now focus on growing. All of this is not the thing I needed to hear today in order to feel better." Well, firstly, I hope that with the first point about not projecting, we've actually realized we don't need to take this loss as seriously as our brain is making us take it. But I also want to say this.
Usually when we make a mistake, there's a combination of our actions and their actions that means that it goes south quickly. In John's case, John sent a message that was reactive because he was scared he was being ghosted. What he was met with was someone who had their own avoidant tendencies because they were scared of someone being too aggressive. And all of a sudden, she didn't say, "Hey, it's really unfair that you said that because my dog just died and I'm in a bad place," which would have given him a chance to apologize. Instead, she said, "Don't message me again." And she just bolted as a result.
So, there was a dance between these two things in both of their nature or their trained responses that meant that it didn't work out. Were John to be with someone who showed maybe a little more grace or was a little slower to cut him off, he might have actually had a much conversation. So, when we are learning our lesson, we have to own our part, but not their part in the equation. And very often, we don't give enough credit to someone else's part in the equation of why it didn't work out.
And the other thing I want to say that's going to make you feel better is this. They are a stepping stone. If we consider the first point I made about not projecting in this situation, not thinking that this was our only shot at love, if instead we realize that there are many people we could be happy with. And ultimately, the person that we end up being happy with is the person that we meet at the right level of healing ourselves and someone who, when we meet them at our stage of healing, understands that we are at that stage of healing and is able to create the space for who we are in that moment.
The question of whether it could have worked with this person is kind of irrelevant. It doesn't actually matter that much because there are lots of people it could work with. The person that it does end up working with is the person that we meet in the right state at the right time, both on our part and on their part. And when we find that person, we will look back on this and laugh at the idea that we had blown up our entire happiness by making this one mistake with this one person.
The last point I want to make in this video is about one key word. Reactivity. I know that so many of us want to fix something with someone we've blown it with. We want to tell them that they're wrong for letting us go. We want to sell them on a relationship with us, on trying again.
The worst thing we can do is come from a place of anxiety and high stress and scarcity and fear. All of that is reactivity. And when someone senses our reactivity, what they sense is a need for a certain result to happen and that we're sending a certain message to try and manipulate the situation to get the result we want. That might mean instead of sending Sarah a message saying, "I'm so sorry. Please don't give this up. I think we have something really special. I have really strong feelings for you. Blah blah blah blah blah." All of which is reactive.
Instead, he says, "Hey, I am so, so sorry. I misjudged the situation. I came from a reactive place. I did not mean to add emotional pressure and pain to a week that already must be absolutely horrible for you. And by the way, I'm so sorry to hear about your dog. I am here if you want to talk. And in any case, it would be great to hear from you again. But I'm wishing you the best right now in grieving because I know you must be going through a very, very hard time."
Now, that's not trying to get a result today. But what it does is it plants a thought in Sarah's mind. A thought that maybe over time detonates. As she realizes after maybe one too many bad dates or feeling lonely or feeling like she doesn't connect with other people as much as she connected with John in their first couple of dates, "Oh, maybe I oversimplified John. Maybe I underestimated John."
And it ends up flipping it because John is terrified that he's lost someone with a ton of potential. The more she thinks about John's reaction to his mistake, the more she might wonder about the potential she has lost out on. And she may just give John that text or that phone call that he wanted back when he was scared of losing her.
If this video is speaking to you, but you realize that you are still in too much of a reactive state to be able to trust the words that would come out of your mouth right now with somebody, I want you to do two things. Go to askmh.com and ask Matthew AI to help you regulate your emotions where you are right now. And once you're regulated, ask Matthew AI, "What are some good texts or things I could say on the phone to this person that would help me say what I really want to say from a calm and abundant place?" You can go and try it out at askmh.com. If you've never used it before, you can try it for free.
And leave me a comment below. I'm enjoying reading your comments so much this year. There's an amazing community that's been forming this year. I want to keep it going. I will be in the comment section right now.
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