Have you ever wondered if you should date a man who’s struggling? In this special 400th episode of the Love U Podcast, I reflect on my own darkest seasons and share why timing—not just chemistry or potential—can make or break a relationship. You’ll hear vulnerable stories, hard-earned insights, and a powerful truth: you can’t build a future with a man who isn’t emotionally ready right now. I’ll also explain why empathy doesn’t mean you have to sign up to be someone’s therapist, savior, or safety net. If you’ve ever dated a man based on who he could be instead of who he is, this episode will shift your perspective. Tune in now—this one could save you years.
What You’ll Hear:
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Celebrating 400 episodes of the Love U Podcast and 3 million+ listens across 220 countries
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Evan shares behind-the-scenes evolution of the show since 2016
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The most popular episode of all time (featuring Lori Gottlieb)
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Personal stories of being passed over in dating due to career struggles
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Why timing, stability, and emotional readiness matter more than potential
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Hard truths about dating someone who’s struggling — and how to protect your future
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Advice on recognizing high-risk relationships and avoiding self-sacrificing patterns
Full Episode Transcript
Hey, this is Evan Mark Katz, dating and relationship coach for smart, strong, successful women, your personal trainer for love. Welcome back to the Love You Podcast. It is a very special episode because as far as I can tell this is the 400th episode of the Love You Podcast.
400 individual episodes will be in the can as of today and that’s a milestone. Over the years I had a blog that you know used to get 12 million readers in a year. We had over a thousand blog posts on that.
Then the internet moved to podcasting. I started this in 2016. The first couple months we were doing this were like literally like top 20 in all of self-help.
It was a really, really cool accomplishment before everybody flooded into the space. Nonetheless, at this point in time, all of these years later, 400 episodes later, the Love You Podcast, I went and did half-assed internet research, is in the top 0.5% of all podcasts. 0.5% of, I don’t know, a billion podcasts? Two billion podcasts? There have been three million listens from 220 different countries.
Thank you to listeners in all the different countries. I assume I’m getting people from the United States, Canada, and other traditionally English-speaking countries but it really means a lot that people listen from all over the world. There have been, at least at the time of this recording, 528 Apple reviews and I think we got like a 4.7 or a 4.8. You can’t help the negative reviews but thank you to the people who said the positive things along the way.
When we go inside our podcast host, hosted by Blueberry, 91% of people who start an episode listen to the full episode. That is something. I think that the secret to that formula is that we keep the podcast relatively short unless we’re interviewing someone, in which case we’ll go for an hour but otherwise you’re gonna discover our podcasts are, you know, 10 to 20 minutes for the most part.
So thank you for listening to these podcasts all the way through beginning to end. Our most popular episode was episode 96. It was an interview with Laurie Gottlieb, a friend of mine who is the author of Marry Him, The Case for Settling for Mr. Good Enough and the bestseller, the New York Times bestseller, Maybe You Should Talk to Someone.
So of all the episodes I’ve ever done, not surprisingly the one where I interviewed someone who is more prominent than me is the one that got the most listens. But I’m just grateful for all of it. 400 episodes in, we’ve covered a lot of ground.
If you go to evanmarckatz.com, you click on podcasts at the top of the way, at the top of the page, we have everything categorized in the categories that we use for Love You. Confidence, Meeting Men, Dating, Understanding Men, Relationships and Commitment. So if you’re a regular listener and you want to check out some old episodes and there’s certain areas that you think are more interesting, do not hesitate to look through our back episodes because they might speak to you as much as the newer ones.
First year of this podcast, first two years of the podcast, I shot it in a studio, like literally rented office space, had a two camera crew set up and those episodes used to probably run for about 45 minutes a pop where I’d have pages and notes and it was scripted. It was a lot more robust and the podcast format has changed over the years. It’s still changing based on the whims of me and you, my audience.
And I guess I don’t know how to say it any better than thank you. I’m grateful that you choose to listen to this out of all the other things that you could be listening to. And certainly the competition is fierce.
I don’t listen to many dating podcasts. I mostly stick to comedy and politics and sports and movies, things that are a little bit lighter than my day job. Maybe politics is not that light but you get the idea.
So when you have a million choices to know that there are a few thousand of you anyway who make this their appointment listening every week, I can’t express my gratitude enough. Thank you, thank you, thank you for listening and for allowing me to be me and share what I know with you and hopefully it makes a difference and hopefully you feel like we have a friendship, albeit a little bit one-sided. I’d like to think we’d be friends in real life.
That’s the nice part about doing this for a living is that the people who listen eventually become clients and then we get to have a real-life experience together and this is not some celebrity influencer podcaster. This is real people talking to real people and I just love the fact that I feel like on this podcast I could be as me as I can be with my wife and you are all part of my extended family. So I didn’t have anything prepared which is why I’m stumbling on.
I’m gonna get to the meat of today’s episode but thank you for making it through 400 episodes. Let there be more. Today I just want to remind you before we dive in, the next installment of the Extraordinary Love Series takes place a couple weeks.
Every Extraordinary Love Series is an amazing event. We’re doing a Zoom call, short lecture, live Q&A on a specific topic. The live Q&A is always a barn burner because I answer your real-life questions.
This month’s topic, How to Identify and Attract Emotionally Available Men. How to Identify and Attract Emotionally Available Men. Go to extraordinaryloveseries.com to register.
Get on the list for free. We’ll send you reminders and I will see you on a private Zoom link in a couple weeks and you’re gonna be joined by hopefully hundreds of other smart successful women who are also trying to make better choices with men. So I want to begin with a story and I realized that when I was doing it I couldn’t figure out a way out of it.
I couldn’t figure it out for the thumbnail on YouTube. I’m really in a good celebratory mood. It’s spring, kids school year is ending, LA is getting sunny and it’s the 400th episode and I realized the topic is a little bit of a downer.
Should you date him while he’s struggling? So I’m not gonna make light of the topic in any way but I don’t want the weighty subject to get in the way of the good vibes here as best I can. So there’s gonna be some sad stories here today and there’s gonna be some hard truths given. First story and forgive the ignorance and the arrogance.
I share my ignorance and arrogance to illustrate points, not to make myself look good clearly. The first time I realized I wasn’t everybody’s cup of tea. I was in my late 20s.
There was a woman I really liked, really respected. She went to Harvard and I remember telling me just casually in confidence she would never date a writer. I was a writer and I couldn’t tell you how devastated I was.
It’s not like we were even interested in each other but she had drawn her conclusions. Writers, lots of passion, lots of creativity. She really didn’t like the moods.
She really didn’t like the economic insecurity and what that did to the person who was a writer and so it was the first time it ever dawned upon me because my parents gave me a lot of love and self-esteem. First time it ever dawned upon me, oh there’s good valid reasons that someone would not want to be with me and that blew a hole in me somehow that I did not have there before because I was so insular convinced of my own value and as I said I share these stories not to make myself look good. Second story.
I’d already forgotten about the first story at this point in time but my life circumstances hadn’t been any better. I’d been dating online for a few years, early adopter of online dating. There was one time I remember I was passed along by women like a joint.
I’d go out on a coffee date with a woman and she’d be like you’re not right for me but I think you’d be right for a friend and I get set up with a friend and then the friend would go out with me and be like you’re not right for me but I think you’re right for my friend. So I was good enough for the friend but I was never good enough. So I was having a moment where my self-esteem was getting crushed and my career was not working.
I came out here to be a screenwriter and write episodes of Friends and Judd Apatow type movies and I remember I went on a date. It was a Jewish dating site and I remember her. I can a German woman in Santa Monica who after the date and maybe on the phone with her afterwards told me that I didn’t need a girlfriend, talking about me, because you don’t need a girlfriend.
You need a shrink. You never forget the mean things that people say to you. Never, never, never forget the mean things people say to you especially when they’re right.
So this is my entry into today’s topic. Should you date him when he’s struggling? This woman was 100% right. I wanted a girlfriend.
I wanted someone who loved me unconditionally, who brought some light to my otherwise dreary life but I was so unhappy at the time. Careerless, penniless, disconnected from my closest friends and family on the East Coast, just struggling to make it through the day. Everybody’s 3,000 miles from home, right, and I’m anxious and depression is hanging over me like a black cloud.
So it was a time in my life that, you know, it’s really the worst time of my entire adult life and I had enough going for me in that, you know, I had a decent sense of humor. I had a decent brain. I had some charm that I could sometimes compensate but the black cloud was always bigger than anything that I can bring to the table.
And so when I was able to get out from under the black cloud and I could get some face time with someone, I could sometimes convince someone to be my girlfriend. I think in those years, 25 to 30, I’ve probably had about three girlfriends but, and this won’t shock you, those women who took me on as a boyfriend were also in a pretty dark place and they were damaged and they were struggling in their lives. And so this brings us to an interesting idea and, you know, I didn’t invent this, like attracts like, which is to say that I might have been a good person and to this day I believe I’m a good person.
I think we all like to think we’re good people but I wasn’t in a very good place. And any woman who was in a good place would not want to be with a guy like me who wasn’t in a good place. The only people who would take on a guy like me were people who didn’t think they could get a happier guy, a saner guy at the time.
The only people who would take me on were people who were also in a bad place, which is why as a rule, to circle back to the original premise, I tell women not to choose men based on just connection or looks or potential. Timing has so much to do with whether a relationship is going to get off the ground. So a couple bullet points to illustrate my larger point.
Have you ever gone out with a guy who is long distance, who was a good enough long distance boyfriend but didn’t want to move to you, wanted you to move to him, maybe you even did move to him but the relationship wasn’t as good in real life when you were together? Hold that thought. Have you ever gone out with a guy who is battling an addiction, whether it was alcohol or drugs, and you tried to stick by his side through it but you couldn’t because he couldn’t beat his own addiction? Have you ever gone out with a man who just couldn’t get his career together and was angry or depressed or emasculated? The entire time you were seeing him, he never really got his act together and you were the sane, stable, breadwinning one? Have you ever gone out with a man who was divorced or separated and was, no matter how strong your connection, he just wasn’t in the place to give you the relationship that you wanted? He wasn’t in the emotional space to make a big lifetime commitment so soon after his divorce or separation so once again the timing was wrong. So we can go on and on and on but the point is that circumstances matter a lot.
Timing matters a lot. It’s one thing if my wife were to abandon me after 17 years because of a bump in my career, I would not expect her to do that, but to tell someone to take on a guy who is chronically unemployed at age 29 or whatever, I don’t blame anybody for doing that. So I think we could agree you don’t abandon your partner who you’ve made a vow to during hard times and that taking on someone who’s troubled is a pretty high-risk maneuver that has a very low success rate because it’s dependent upon that person or those circumstances changing and I think most of us operate similarly.
I desperately wanted someone to take a chance on me when I was at my lowest. Who among us wouldn’t? But I also know there were people that I took a chance on when they were in a bad place and I did it based on attraction and loneliness and I usually ended up regretting my own decision because you can’t save someone from themselves. I remember years ago on my blog I answered a question from a woman who was writing to me because she had a therapist and she did not like the advice her therapist gave.
Her story was this, she’s a clinically depressed woman, but really clinically depressed, not circumstantial, like I’m out of a job or my kid is sick. It was clinically depressed to the point where she was non-functional. She couldn’t even hold down a job because of her depression.
So you could feel for her and so her therapist said, hey if you’re in such a bad place that you can’t even take care of yourself, you might not have much to give to a romantic relationship, you should probably put the gas mask on and take care of yourself first. She didn’t like that so she wrote to me and I largely told her the same thing. She might not be in the best position to date if she could not take care of herself and I naturally, because it was the internet even before social media, I got yelled at by depressed people across the internet who said how dare you, how dare you say that to her.
So here’s the thing, as a guy who’s dealt with both anxiety and depression, 95% of it before I got this career, I don’t think one can deserve love any more than one deserves to be a millionaire. In a perfect world everybody’s rich, everybody’s happy, everybody’s in a healthy relationship. It’s just not that world.
In reality, life is unfair and capricious. It is. Just look around.
Life is unfair and capricious and shit happens and people are born into bad circumstances or circumstances happen to them against their will and you just can’t force anybody, guilt anybody into dating you even if you might want to. You can’t. People have choices, people have options.
I remember the last time someone passed me up because of my career. I even remember her online name, it was Dream Maker. I don’t think she’s listening right now but her name was Dream Maker and at the time she was 30, I was probably 29, we went out for a few weeks.
Things were going really, really well but she was divorced, she very much wanted to get remarried and have kids and I was the guy who just took a job answering phones at J-Date. Maybe I was beginning to work on my first book at the time. I was making 30 grand a year.
She, after a few weeks of dating me and really liking me, just didn’t want to bank on my potential that may or may not get realized. So I understood. I didn’t like it but I understood and I remember defensively when she said goodbye, I remember telling her that I was going to be successful one day but she would end up with some bland lawyer who didn’t make her laugh, couldn’t turn her on, that was what was going to happen to her if she passed me up.
It was the act of a desperate man and she said, who knows, you may be right but she had to take that chance. She couldn’t bank on me becoming a successful writer. As it turns out, I got what I wanted to.
She did not. I became financially successful and happily married and had kids and she never put it all together. I don’t even know how I feel about that.
I don’t have any shame for it because she passed me up but she was a lovely person and I feel bad that she never got the thing that she wanted the most. I don’t know how her circumstances changed or what led her to that of course but the reason I share this story and I share all these personal stories is because I don’t blame her for her choice at all. She didn’t get to know my character, she didn’t know that I was hard-working and creative and I was on an upward trajectory.
All she knew is that I was a penniless screenwriter and that’s not the guy you marry if you want to start a family and live in Los Angeles. So to bring my story back to you, I get that it’s hard to find a strong connection with somebody but as your dating coach, at least in these circumstances, I try to be your dating coach. I try to advise you as if I would advise a client.
My job is to be your risk manager because when it comes to dating, people take terrible, terrible risks with their love life and as we say in LoveU, I hinted at it earlier, you can’t have a relationship dependent upon someone changing for you. If your guy is not in a good place when you start dating him, you can’t count on him ever getting there. You’ve got to assume this is it.
Find a guy who today, not six months, one year, two years from now, is going to be emotionally available but now, emotionally available, financially stable, commitment oriented now, not dependent upon him moving, not dependent upon his divorce or him leaving his wife. We can’t keep on banking on these circumstances and if we have the courage to say no to these sinking ships, then you will never have to waste your time on a guy with potential that goes unrealized ever again. That’s a really, really powerful lesson.
So we could have empathy for people who are struggling the same way you want people to have empathy for you but that does not mean you have to take on a man as a project and hope that if things break just right, it’s gonna work. We want a guy who’s ready-made. We want the house that we’re ready to move into right now.
Only those guys. Learn to say no to the other ones and only focus on your guys who are in a good place in life, who are ready for you and you’re gonna have a much better chance of successful relationships. Thank you again for listening to me, for allowing me to be myself, for being with me through 400 episodes.
Please subscribe on Apple, please subscribe on Spotify, leave us a positive review, tell a friend. Don’t forget the Extraordinary Love Series. Go to extraordinaryloveseries.com next month’s episode, How to Identify and Attract Emotionally Available Men.
I’ll be doing a live Q&A to take your questions about how to attract an emotionally available man and finally, if you are tired of wasting your time on the wrong men because you sunk too many years into projects and men who fail to live up to their potential, good men exist, I promise. Go to evanmarkatz.com/now, book a time with me, we’ll talk, I’ll get to know you and we’ll figure out the best course of action for you so you could finally get the love that you deserve. Thanks again for your time, I appreciate it.
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