How to Know When to Leave a Relationship | Matt Monday
25 Aug 2025 · 27 min
In this episode of the Matt Monday podcast, host Matthew Hussey and co‑host Speaker E discuss the difficult question of when to end a romantic relationship that still feels loving. They explore the difference between love and compatibility, the role of shared vision, long‑term happiness, and the emotional obstacles—guilt, fear of being alone, ego, and uncertainty—that keep people in unsatisfying partnerships. Hussey offers a series of reflective questions for listeners to assess whether a relationship truly fulfills them, emphasizing the importance of teamwork, honest communication, and feeling seen and accepted for one’s authentic self. Throughout the conversation, the episode intersperses several advertisements (Sleep Number, Progressive Insurance, Mint Mobile, HeroBread) and promotional segments for Matthew AI—a digital coaching product—and an upcoming relationship retreat. The overall tone is conversational, empathetic, and encouraging, aiming to help listeners identify red flags, understand their own needs, and make confident decisions about staying or leaving.
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Foreign.
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You know when you hear something like that, it's worth asking the question what is it about the roses? And then saying what does that speak to in what's missing from this relationship?
Foreign we have some people who are trying to communicate with us about relationship advice that they so desperately need. Are you ready to dive in?
I think so.
Well, you just never know.
Made it sound like it was something terrible was about to happen. I never know it's gonna burst through the door.
I don't know what they're gonna say.
I don't know what's going on. I think I'm Ready?
Okay. All right. Someone asked, how do you leave a relationship you know is not right for you, even though there is a lot of love there?
Well, I'm assuming this question is not being asked. It sounds like this question is being asked in the context of a relationship that's not satisfying, as opposed to a relationship that is in some way making her suffer. So. Or him. I don't know if this is from a. A guy or a girl, but that situation where you say, there's just a lot of love there, love isn't enough. Love is not all you need. What you need is compatibility. And incompatibility shows up in a number of ways. And I think you have to ask yourself, regardless of how much I love this person or how much this person loves me, are we compatible? Do we have the same vision for what we want to build? Can I build what I want to build with this person? If things stayed the way they are today, could I be happy? If it just stayed the way it is today? 10 years, in 20 years, am I happy or am I unhappy? And those things probably aren't going to get better. Right. In many ways, your resentment, your frustration may get worse.
Yeah.
So I would ask myself, what is it? I need to be different in this relationship to feel like it's not just one where we love each other, but it's fulfilling. And then if I had any doubt, I'd say, let me try to create that with them. Let me enroll them in trying to create that with me. And let me see if. Let me also see if there's a desire on their side to get there. Because that's the other thing. Sometimes you're with someone who you say, I'm not satisfied here. But you don't have someone who says, oh, my God. If that's the case, let's figure this out.
Yeah.
You have someone who's, like, indifferent to it.
Right.
Or they don't want to know, or they want to sweep it under the rug. And that's a problem because now you have a desire for it to get better and they don't. And you. I think that's why. I think one of the highest values in any relationship is teamwork. Because if we encounter something like this together, we could share it with each other, and we might have a real stab at the two of us fixing it together. Yeah, but if one person is really motivated to do something and the other one isn't, there's a whole different problem. Even if you're both motivated to fix it, it doesn't mean, it will get fixed. Yeah, but at least you have a shot. So find.
I mean, I just wonder from all of the people that you've talked to advised, like, do people really know when they say, like, I want, I just want to be happy or I just want to feel fulfilled, like, what that even means? How do you even pinpoint what would make you happy? Because one person could say, well, it would make me happy if my husband came home every day with roses. Okay, like, okay, but does that make you fulfilled? Like, what actually fulfills you in a relationship? How do you figure that out?
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Yeah, and I think it's the. What's behind the roses? Like, what are the roses about? Because it's never about the roses. Right. You could buy yourself roses. Why is it you want your husband to buy you roses? Like, what's. What's beneath that? Is it you want to feel seen and you don't feel seen right now? Is it you. You don't feel thought about? You feel like they work all day and then they come home and they sit in front of the TV and there's no thought for you. There's no thought for your experience. There's no thought for the relationship. Maybe what you want is in that person's busy, busy day where clearly their work is a major priority to them, which is fine. You also want to feel like the relationship is a priority for them. And the roses just for you would be a symbol of the relationship. Gets air time, gets bandwidth in your mind.
Yeah.
At the same time as these other things. And that could be shown in a hundred different ways. But. So what is it, you know, when you hear something like that, it's worth asking the question, what is it about the roses? And then saying, what does that speak to in what's missing from this relationship? You know, if it's your partner is, I don't know, always late for every day? Or they, you know, they are constantly. Yeah. You know, they arrive on every date in a late and chaotic way and it just makes you stressed and you feel like it's, you know, it makes you unhappy? Ask yourself, what is it about this that makes me unhappy? Well, you know, again, it might feel like, oh, the date is always an afterthought, or they, they can't prioritize that moment that they spend with me. Or they don't put nearly the forward planning into the vision for our relationship as they do into all of these other projects in their life. And it might be for some people that lack of satisfaction is sexual, or it's in the chemistry that they don't anymore feel in the relationship. And again, it's like, okay, so it, and this depends how deep you are into the relationship, of course. But if you're in a relationship where there's a lot of love there, then it might be worth you saying what's, what is going on here? Like, what is really happening? Is it that we've stopped communicating about who we are and what we might enjoy or what would excite us? Like, have I stopped telling you? Have you told me in however long? Like, do we even know each other still in that department? Like, or are we pretending we do, but really we don't? We're speaking different languages. And if there's a lot of love there, then, you know, I'm. There's. There's a lot of love there means one of two things. It either means I'm just scared to give up this love because I don't think I'll ever find love again, or it means there's something worth saving here because we have a deep love for each other and we truly see each other and we've been through a lot together. And so you have to ask yourself honestly what that's about.
Yeah.
Is it that you think there's something truly valuable to hold on to that you would be dishonoring it by just cutting and going.
Yeah.
Or is it that you're just. That's a euphemism for, I'm not happy. This isn't the right relationship for me, but I'm afraid to leave someone who cares about me.
Yeah. Oh, I've been there too. And it feels like, it's like a guilt. Like you're like, this person hasn't done anything wrong. They haven't done anything to me personally. Like, they're a good person and I love them and they love me. So, like, what's wrong with me? Why I can't just be happy with this person? But, like, I don't feel like in relationships and in love and if we're talking about like long term love that we should just be happy with whatever it is that we're getting if it's not fulfilling.
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Why Choose a Sleep Number Smart bed Can I make my site softer?
Can I make my site firmer? Can we sleep cooler?
Sleep number does that cools up to eight times faster and lets you choose your ideal comfort on either side your sleep number setting. Enjoy personalized comfort for better sleep night after night. And now during our President's day sale, take 50% off our limited edition bed. Shop now for a limited time only at a Sleep number store or sleepnumber.com.
And sometimes our guilt is a cover for our fear. Guilt is an easier place to go, a more palatable place to go than the bigger disappointment of I haven't found the kind of relationship I really want. And I'm, I'm going back out there to be on my own again. And that scares the hell out of me. And it makes me worry that I'll never meet someone who's right for me. And therefore I'm terrified.
Yeah.
Of leaving. It's harder to, to truly feel your disappointment than it is to say I feel really bad.
Yeah.
About hurting someone's feelings.
Well, that's the funny part of when I went through that breakup. The first part was guilt and the second part was holy. I haven't been single in however long. Like, what's gonna. Who else is out? Who else is out there? Like, who else is gonna put up with me? Like, who's gonna, who's gonna, who am I going to even be interested in? Because like I said, I, I, I've, I never get that, like, visceral reaction. I have friends who my sister, one of my sisters falls in love every weekend. She's always like, I fell in love last night. I'm in Love. And then the next day she's like, I. Who? Like who are you talking about? I don't even know who that person is, but I never get that feeling. So when you give something like that up, it can be very scary to think like, oh, I'm out here on my own and this is like new frontier. And who else is even going to be out here? But I think that the fear of. The fear of not finding out scared me more than the fear of finding out. And so I was like, okay, I have to. And also, it's unfair to the person when you're not. When you're not fully invested.
Well, you only have to consider what it feels like. I know I've been on the receiving end of someone else who's not sure. And that's a special kind of hell when you can sense that. It's like someone's not quite there with you. They may not be saying it, but you can feel it. It's a deep, deep feeling of insecurity that you have around that person. It erodes your self esteem.
Yeah.
And it makes you feel crazy.
Yeah.
Because you typically don't find out for sure that they've been having doubts about you until the day they break up with you.
Yeah. Or.
And then on the day they break up with you, you feel like, what planet have I been living on that I've been happy? And you've been questioning this for so long. So it's, you know, you have to also consider that when you're unsure, there's a very good chance the person on the other side of that is experiencing that uncertainty. But because you're not saying it, they're internalizing it as some form of something's wrong with them. Why am I anxious? Why do I not feel good? Why do I not feel as loved as I'm loving this person? So that's a, you know, we do as quickly as we can make our mind up. And I have no righteousness about this because, my God, the number of times in my life I took too long to make my mind up. Those are regrets I have hurting people. But we do you know, any. Anyone who feels guilt and wants to take that at face value should say to themselves, if, if I were on the receiving end of uncertainty, it would be a very painful thing for me to experience. And you're giving them the real shot of finding what they deserve, which is someone who's actually sure about them. What we have to live with is that they might find someone who's sure about them. And we're the ones who now are trying to.
Oh, my God.
We're the ones who are alone, not them. Which is, you know, often happens. We leave because we're not sure. And then, you know, we.
They.
They go on to find someone else because we've made space for them to do that. And we're. And we're now going out into the world alone and trying to find love. And I know I used to have this feeling. Anytime I would leave something that didn't feel right, I. I would have this sense that I was going to be punished for it somehow. I would have this sense that I'm. This is. There is some kind of punishment for me letting go of someone who loves me so much, who. And. And I'm not happy. This. Somehow, this is not gonna end well for me.
Yeah.
But I. I think there's no easy answers to these things. But I know that my wife today. There is a kind of bond there. And in. In some really fundamental ways that are important to me. I am so happy that I made space for that to happen.
Yeah.
Because I really would have missed out on the greatest experience I've ever had of a relationship. I would have robbed myself of that. And I think that hopefully we get to a point in life where we start realizing some of the things that we've been chasing that aren't important, and we start realizing some of the things that are really, really important to us. Like, I know my. My connection. My intellectual connection with my partner where we could talk about anything and, you know, laugh about things together and. And we can just talk. We can talk. And it. She's just. It's always interesting, and she's always. Whatever it is I'm doing, she's quick on the uptake and vice versa. There's. That, to me, is like, become one of the things that's most sacred to me. I could. You know, it doesn't matter what level of, you know, attractiveness anyone in the world was. If I didn't have that, I would have. It would have been a really lonely experience for me.
Yeah.
Being in a relationship. And I think when you know that, you realize, like, oh, this is. This has to be prioritized as one of the most important things in the world. But what's hard is sometimes I think we're following our ego without realizing it. We're not following what will make us happy. We're following what will satisfy our ego. And that's what a lot of people do. They find someone who's like, looks the part.
Yeah.
Has a certain amount of cache or success or status or something. There's something. Or is super charismatic or there's something about them, the way they are in a room, the way they are with other people. And our ego says, hold on to this person.
Yeah.
They're. They're popular. They're called.
They're sexy guys.
And it. And it. But it's ego taking the wheel. And at some point, we have to go, what's going to drive for me? Is it my ego or is it my soul? Is it what makes me happy? You know, this person might not be, like, there might be people you've brought home in the past who, you know, your friends are all like, I mean, this person's so hot. Good for you. Like, and that feels really good. And it makes you feel like you should hold on to that person.
Yeah.
But the person that you bring home and the first time, everyone's like, they're really. They seem like a really nice person. Like, that might not satisfy your ego as much. Yeah, right.
Like, he treats you really well.
I remember when they.
I brought home someone and you said they were gorgeous. Yeah. Oh, my God. You know, like, you were swooning.
Yeah.
But that person maybe turned out to be the most hellish relationship of your life.
Right.
And meanwhile, you've got someone that, you know, everyone doesn't swoon the moment they walk into a room. But. But guess what? They make you happy. You feel good around them. You feel like. I think this is always an important question. Who, when I'm around them, do I feel more of myself?
That's the most important thing. That's the most important thing. I remember when my now boyfriend and I got together and I was describing him to my sisters, I was like, I just feel like I can be who I am when I'm with y'.
All.
With him, that's a huge sign.
Like, I can be my weirdest, most creepy. Whatever. Like, my sisters and I are. We're weird. Like, we're weird. There's six of us. Like, we're crazy, kooky, screaming, singing weirdos. And I can be that with my boyfriend. And he joins in. And then when they met him, they were just like, he just fits. Like, he's just like. It's like he's always been here. And that. That, to me, said a lot because I've always felt like in relationships, I've had to hide or dumb down certain things or, you know, like, just be a version of myself that I thought somebody else would like. And that's not sustainable. That's not sustainable. And that's not, that's not really what love is about. Especially not like when we talk about unconditional love or like love that can, can, you know, withstand the tests of time. Like that's, that's, it's something different.
Well, we want to be seen.
Yeah.
That's the, that's the. I think one of the most important things is we want to feel seen by someone. And that means that's incumbent on us to share things. Because that's how we get seen.
Yeah.
Is to actually share parts of ourselves. But then when we feel acknowledged for those parts and we feel like the person opposite us understands those parts of us or learns to understand those parts of us and accepts them, that's like. I mean, that truly is the greatest feeling on earth.
Yeah.
It's the feeling I'm most grateful for, honestly.
Leave me a comment on this video before you go. I love hearing from you. And by the way, if you're watching this and you really want to find love and you see other people around you pairing off and finding what you. You've been looking for for a long time and you're feeling like when's it going to be my turn? How might I be getting in my own way? Is there something I'm doing to sabotage my chances in this area? How can I finally find what I'm looking for? I am going to be helping people uncover their deeper patterns, understand their blind spots and find what they're looking for this October at my retreat. If you have a got a ticket yet, you can get your tickets@mhretreat.com and don't worry if you can't make it to be there in person. In Miami with us there is a virtual ticket that means you can participate in this event and get the content from it from wherever you are in the world. Go check it out@mhretreat.com grab your tickets and I can't wait to see those of you who are coming.
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Can I make my site firmer?
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