Have you ever had an amazing connection with a man—only to find yourself heartbroken and confused when it didn’t last? In this Love U Podcast, I break down the three sneaky but predictable reasons relationships fail, even when everything feels right: timing, circumstance, and location. If you’ve ever fallen for a guy who wasn’t ready, was juggling too much, or lived too far away, this episode is for you. I’ll help you spot these traps early so you don’t waste time on someone who can’t go the distance. Tune in now to protect your heart, trust your instincts, and date with confidence.

What You’ll Hear:

I break down the heartbreaking pattern so many women face—going from “he’s the one” to wondering what went wrong.

You’ll hear the three biggest reasons promising relationships still fail: bad timing, messy life circumstances, and long-distance dynamics that feel romantic but rarely work.

I explain why chemistry and connection aren’t enough—and how even great guys can derail your future if they’re not ready or available in real life.

I unpack how to spot these red flags early, before you invest months (or years) trying to fix something that was never sustainable.

You’ll hear stories of women who bet on potential, ignored timing, and ended up stuck in relationships that drained them—and how you can avoid the same fate.

I give you clear, actionable dating wisdom so you stop choosing “maybes” and start making smarter decisions that lead to lasting love.

And finally, I share why the right relationship isn’t supposed to be hard—and how to know when the timing, circumstances, and location are finally working in your favor.

Full Episode Transcript:

You have the deepest connection. You’ve never felt anything like it. You both agree that you just know that you finally met your person, the one.

One year later, you’re single. You’re depressed. You’re devastated, and you’re trying to make sense of where you went wrong.

In today’s episode, I’m going to tell you. My name is Evan Marc Katz. This is the Love U Podcast.

This is an episode you absolutely want to stick around for because I’m going to be dropping some real hard-hitting, truth-telling knowledge. But you’ve got to stick around until the end. This podcast is sponsored by absolutely no one.

So, to spread the word, make sure you subscribe on Spotify. Subscribe on Apple. Leave us a positive review, et cetera, et cetera, et cetera.

It actually means a lot, so make sure you take care of that. If you haven’t already done so at some point in time. And before we get into the nitty-gritty of today’s podcast, I want to remind you that the Extraordinary Love series continues on.

It grows by about 100 people every month. I do a live Zoom call with a live Q&A on a very specific topic. The next month’s topic is what high-quality men want in a long-term partner.

Join the movement. It is now a movement. Once you have over 500 people, it’s got to be a movement, right? So, join us on the Extraordinary Love series.

Extraordinaryloveseries.com. Put in your name, email address, and phone number to get reminders. And now, without further ado, three reasons your relationship will likely fail. Now, I don’t want to be a pessimist.

I’m a dating relationship optimist. You couldn’t do this job if you weren’t. But you don’t have to be Nostradamus to recognize that most relationships do fail.

So, this title is not remotely controversial. If you were texting eight guys on Bumble now, if I were a betting man, I would bet against any of those eight guys on Bumble being your future husband. So, that’s where we come up with the love you idea of long-term, short-term optimism.

Sorry, I got it backwards. Short-term pessimism and long-term optimism. We don’t expect anything from any one guy.

And at the same time, there’s 70 million married people in America. Half of all couples start online. There’s no reason to be a pessimist about love when many, many, many people still fall in love and get married, especially people who are college-educated, six-figure earners are the most likely to get married.

So, no need to be gloom and doom. That’s not the point of this podcast. I just had to slip that in because it’s always important to remember you could be a short-term pessimist and realize that most relationships don’t work, but if you play your cards right, there’s every reason to think that you will get happy again one day.

So, this is a podcast for people who want to make good relationship choices where the stakes become higher. We don’t expect anything from one guy, but eventually you’re going to meet a guy and you’re going to have sex with that guy and you’re going to open up to that guy. You’re going to introduce him to your friends and your family.

You’re going to talk about a future and you want to know that you’re doing this with the right person because you can meet someone and feel a deep connection. You could be perfect on paper and you could run a simulation through a computer and discover most relationships will still end in failure. Why? When you have a deep connection, he has a deep connection with you and everything looks perfect on paper, will relationships still end up failing? That’s what we’re talking about here today.

And there are three reasons that are kind of obvious that I haven’t heard put into a little listicle before, so we’re going to do that today. Number one, timing. Even the right person at the wrong time could be a broken relationship.

So, here’s some examples. There are infinite examples of this. He’s separated and emotionally raw.

Now, maybe he’s been separated for a week, but maybe he’s been separated for a year or two. So, you come along. He’s been in a loveless, maybe sexless marriage for a long period of time.

He throws everything into his relationship with you. You fall deeply in love with each other and this feeling, this relationship is real. We’re not minimizing what you’re feeling.

The problem is two years in, you’re looking to get a wedding ring often, right? And the ink is just drying on his divorce papers. So, you’re just in different places in terms of what you want. He might be a great guy, but he might be a great guy who you’re meeting at the wrong time in his life, where your needs are different and it doesn’t mean there’s any bad actors, right? Or imagine a scenario where you’re thriving in your career, but his career is tanking.

Maybe he’s been downsized in his middle age. Maybe he’s no longer motivated. Maybe he went out of business because of market circumstances, but he is on shaky ground.

Maybe he’s unemployed and he’s not bringing in anything, but he’s certainly not going to be the best version of himself. He’s not going to be that confident. He’s not going to be as masculine, ready to protect and provide and take care of you, since he could barely take care of himself and he’s probably feeling like a shell of himself.

So, another example of where it doesn’t mean he’s not a good man. He’s a good man at a bad time in his life and until he gets back on his feet, I would not really entertain it. It is not your job to see him through this time.

It’s not like you’re married for 20 years and he lost his job. This is the guy you just met. So timing really, really matters.

The most obvious example of timing is you’re 38, he’s 34. You very much want to start a family and the guy you’re dating is maybe open to marriage. He could be open to kids.

The maybe guy is the most dangerous guy because you hear, oh, I could work with this. I like him. I love him.

Maybe could mean yes. Yeah, and maybe could also mean no. You could sink two years into a relationship with a 34-year-old man.

You’re now 40. He’s 36. And you’re thinking, all right, so we’re doing this.

And he’s like, I don’t know if I want to get married and have kids. And now you’re there holding the bag. Easily avoided if you don’t date the maybe who isn’t sure if he wants to get married, isn’t sure if he wants to have kids.

He’s just a different person at a different time and you banked on your connection and the potential. So love is not just about chemistry. We know that.

But chemistry takes on a disproportionate weight. Alignment and timing is as important because you could have all the chemistry. You could have everything add up on paper.

But if you find a guy who’s at the wrong time in his life where he is not ready to build something with you because something’s broken in his world, doesn’t matter. And I wouldn’t even get started on a relationship like that. You’ve got to come from a place of abundance to be able to say no to a great connection with a guy who has some external timing issues that are going to prevent him from being a good boyfriend and future partner.

Second thing, and I realized as I was writing this, it’s a little bit like the first thing. And I separate it from timing. I call it circumstance.

So circumstance, I mean that’s just life conditions. Shit happens. So imagine you’re dating a single dad.

You’re both in your late 40s. And suddenly his unreliable ex-wife can’t handle anything. And so he’s got full custody of kids.

Now he doesn’t have every other week off or weekends free. He’s the guy who’s got the full-time job. That’s going to take energy and time away from you.

Doesn’t mean he’s a bad guy. But it might mean your relationship is not going to be what you want it to be. And you’re going to be squeezed out by his lack of quality time because he can only give so much when he’s the full-time parent.

I’ve got a lot of women who work with me who are the full-time parent. They know exactly what it’s like. But you’re going to have to accept less from your partner.

Not everybody gets that. Maybe you fall for a guy who’s in start-up mode. There’s another circumstantial thing.

You’ve got a hard-working entrepreneurial guy, leaves the big corporations, goes into start-ups. Start-ups are notoriously hard for the amount of hours that they demand. So your guy barely has time to sleep.

Or maybe he’s on a law firm track and he’s working 60, 70 hours a week. It’s really exciting to know that you’ve got an ambitious, successful guy who can take a luxury vacation. But you might not get much of a partner out of that.

So whether his whole personality is the workaholic and you finish second, or this is a time of his life where he’s working 70 hours and he might be able to see you for three hours on a Friday night, that relationship might work for him. Hey, it’s great to have a girlfriend who’s waiting for me when I get out of work all bleary-eyed. But it might not work for you.

And I have a love you saying, you can’t have a relationship with a man dependent upon him changing for you. Yes, circumstances can change. I just don’t like waiting for them to.

You really want to meet a guy who’s at a good time in his life, at a balanced time in his life, where he does have room for you. Another circumstantial thing. You meet a guy who is sober, but he is in active recovery.

It’s not that far away from it. So he’s just trying to regain his footing, trying to regain his faith in himself and his trust in his friends and his family. He might not have much to give in terms of building a life with you if that’s what you’re looking for.

So no shade on people in recovery. Just know that there’s only so much hard things we can do at once, I’ve discovered. I’ve talked to people who were in the process of moving or switching jobs or losing weight, and it’s detracted from their focus on their own dating coaching.

There’s only a finite number of hours in the day. So when someone is taking on a big project at the same time he’s taking on love, sometimes those circumstances, and in reverse, by the way, if you feel personally indicted by anything I’m saying, that’s often useful too, to maybe not look for love when you are in major transition with something else. So I’m not trying to stop you from finding love, but I really want to make sure that you know that there’s really good circumstances.

When people hire me, it’s usually in those best circumstances. I’ll circle back to that at the end. So circumstance has a lot to do with love.

It’s not about blame. We don’t have to blame guys for having shit happen in their life that knocks them off course. It is just realizing that alignment and timing has so much to do with whether relationships are going to work.

My story, you know, I wouldn’t have chosen my wife when I was 32 because she was in a relationship with someone else. I wouldn’t have chosen her when I was 36 because she would have been 39, and if I wanted to have two kids, that would be high risk. The only time I could have met my wife was the time that I did, when I was 34 and she was 37.

That worked. We pounced on that opportunity. But the same two people meeting at different times are two ships passing in the night, and that’s okay.

You’ve got to choose your spot. Third thing that causes relationships to fail more than we want to acknowledge, and I don’t know why everybody on the internet isn’t on this train, but I will keep on pounding this, is location. Long distance relationships are set up to fail.

I’ll give you three reasons why, so we don’t have to do a whole podcast about it. I’ve already done a whole podcast about it, but long distance relationships are high risk for three main reasons. Number one, your relationship isn’t real until you’re together.

It’s vacation love. It’s a fantasy. Two people could fall in love at Club Med and be from different states or different countries and try to keep it going and fly back to see each other.

But until you’re actually together, it’s pretty much vacation love, which means it’s fun and easy and exciting, but it hasn’t hit reality yet. Number two, someone has to uproot their life for it to work, so you can have a genuine connection with someone long distance. I’m not taking anything away from it.

There are long distance relationships that work. My sister is in one, but for it to work, my sister had to leave New York and move to San Francisco. That’s a high risk move, especially if when they move in together, they realize their relationship isn’t as strong as it was when they were talking on the phone.

Very, very different circumstance. So someone has to pick up and uproot their life and leave their friends and family or sell their house, and that’s a high risk move for any relationship. Another third thing that dawned upon me relatively recently is that it’s really easy for an avoidant guy to stay in a long distance relationship.

In fact, it’s a perfect relationship for a guy who doesn’t want that full integrated partnership, out of sight, out of mind. He can see you once a month. He doesn’t have to deal with the day-to-day bullshit very much.

And for a guy who wants to keep some distance, a literal long distance relationship is perfect. And it’s not always easy to tell that that’s literally all the guy wants. That’s why he chooses a long distance relationship.

It’s like having a mistress. What’s the lowest maintenance relationship I could have? Not what’s something where I really want to build something with someone. So it’s very easy to get caught up in a relationship with a guy who doesn’t really want a full relationship.

It works long distance. It doesn’t always work up close. And you’ve probably seen evidence of this over the years.

So there’s plenty of examples of long distance. We don’t have to go into all of them. He lives in Boston, and he’s tied to his career.

And you’re a digital nomad in L.A., but you really want him to come to you because you like the West Coast. And people tend to get anchored in a place. And even if there’s the willingness to move, it doesn’t always mean that the move works out.

And now you find yourself in a new city because of someone that you broke up with. Or the commute, right? We think we can make it work. It’s only two hours away.

But eventually it becomes kind of draining to go back and forth two hours every Friday night in rush hour traffic. And fatigue builds, and resentment builds. And it’s just a harder relationship.

So it doesn’t mean there’s no examples of it. I’ve got a client who I interviewed for this podcast named Victoria. She’s got a boyfriend.

They’ve been together for years. He drives six hours to her. It’s a great setup for her.

But he drives six hours to her. I don’t think that happens very often where a guy’s going to drive six hours to you and not ask for anything back. So buyer beware.

It’s not that it’s impossible, but I think it’s high risk, and I think it’s better avoided. Compatibility, right? How the system works. Location is part of compatibility.

And we can’t just sort of pretend it’s this one minor X factor. It’s a huge factor. So in my world, if I’m giving sort of top-down advice from people, I’m trying to avoid predictable things that you could pick up within the first five weeks of dating.

And if we go through this whole thing, if we just go through this podcast and talk about things that you’ve probably done in the past that haven’t worked, we’ve touched on a bunch of them. Long-distance relationships, relationships with men who are at a bad time in their life, whether it’s employment or addiction or issues with ex-wives and kids, guys who don’t know if they ever want to get married, guys who don’t know if they ever want to have kids, guys who are just sort of general maybes. These are absolute no-nos that people think, well, but isn’t that most guys? Yes, that’s why we avoid most guys.

That’s sort of the point. If you go to evanmarckatz.com/10men, I think you can download a PDF that outlines, here are the 10 guys that you avoid when you’re dating. And they’re the guys that we talked about here today.

It doesn’t mean you can’t have a connection. It doesn’t mean you can’t genuinely love them. It doesn’t mean they’re bad men.

It means the circumstances of their life are such that it’s unlikely that a pairing is going to work. And you don’t have to sink one year, five years, ten years into them. You can figure this out in the first five, six weeks of dating before you become boyfriend, girlfriend, before you sleep together.

It doesn’t take long to have these guys reveal these things about themselves. I can’t tell you how many people I’ve coached over the years who are in three-year, five-year, seven-year relationships with guys where they were in so deep they had such sunk costs trying to figure out how to get the long-distance guy to move to them. To get the guy who didn’t want to get married ever to propose to them.

Or the guy who doesn’t want to have kids is kind of kicking and screaming about you putting pressure on him. Or the guy who is a workaholic, you’re making him feel guilty and he’s blowing up at you that he’s working for you. God, how many versions of this story have we seen? So it doesn’t have to be that hard.

I know people glorify relationships take work. I don’t glorify that. A good relationship is easy.

And the best time to do it is when you’re at a good place in life. I have people on my mailing list for five years, ten years. There’s recently a woman who was 50.

She told me she got on my list when she was 50 when she was first divorced. She didn’t hire me until 60. Why? Timing.

She was working on herself. She was getting over her ex. She was losing weight.

She was trying to get on her own two feet independently to see what life was like without him. She was raising kids. She was busy at work.

There was always very valid reasons as to why someone doesn’t hire me. The people who hire me are the people who are like, I am ready. Life is good.

What I’m missing is a partner. That’s the timing of the man that you want to meet, a guy who’s really ready for you instead of trying to make circumstances and timing and location not matter because they matter so very much. So if you’re at a good place in life right now, this is the time.

Your next action, go to evanmarckatz.com/now. Book a time to talk with me. I’m just going to ask you questions about yourself.

Listen to your answers. Make sure that you’re doing something proactively, not just listening to a podcast, which is informative, but taking active steps to date and choose higher quality men who are emotionally available and treat you the way you deserve to be treated. I’m pulling for you.

Thank you for listening. This is the Love You Podcast. My name is Evan Marc Katz.

If you haven’t already given us a positive review, please do so. If you have not subscribed to the Extraordinary Love Series at extraordinaryloveseries.com, it is free. It’s a live lecture, a live Q&A, the ability to ask me questions and have me answer them.

It’s my pleasure. I love doing it, so I hope to see you there. And as always, I love you, I appreciate you, I thank you for listening, and I look forward to seeing you again next week.

Take care. Bye bye.