Reading: How to Reinvent Your Love Life After 50


How to Reinvent Your Love Life After 50

Looking for love in midlife? Dating guru Evan Marc Katz is your new best friend

with Evan Marc Katz

Questions about dating 50 plus? This conversation is for you! “When you choose better men,” says author and dating coach Evan Marc Katz, “The whole world opens up the same way that if you ate healthier food versus eating junk food.” With more than 35 million readers on his blog, 2.5 million podcast downloads, and 13,000 women transformed through his Love U course, Katz is the go-to guru for smart, successful women seeking romance. Discover why Katz believes men look for sex and find love, why your next partner should complement rather than clone you, and how to navigate the dating world with confidence, not checklists. Plus, snag his FREE exclusive gift for listeners: a 25-page PDF on the seven dating mistakes you’re likely unaware of.

Dating coach Evan Marc Katz is the author of 4 books and has been featured in hundreds of media outlets since 2003. His blog has over 35 million readers, his podcast has over 2.5 million downloads and 13,000 women have taken Love U, his video course that helps smart, successful women find love. Evan is happily married and lives in Los Angeles. Connect on Instagram, Facebook, TikTok, Youtube.

LJS: So welcome, Evan. I’m so glad to have you here, and I love the fact you remember that we were together in a very funny situation before, and I thought it would be a great place to start this podcast. So, first of all, you have an incredible memory. My memory is, like, washed out from all those years in publishing. Tell me what you remembered and where we met originally.

EMK: Well, Lesley, thank you for having me on the show, even though you don’t remember who I am. I give dating and relationship advice for women. And, about 17 years ago, you and I had a very loosely scripted five-minute debate on the CBS Early Show about whether women should lie about their age in online dating profiles. And we took opposite sides, although we could probably find a point of agreement on the subject.

LJS: Hilarious. And so tell them that I was saying that you have to say your age and be who you are. And your response was? Is?

EMK: My response is that women lie about their age not because they’re liars, but because they’re practical and they want to be seen, and they could be invisible, they could be shooting themselves in their own foot. And so it’s not that you’re wrong to embrace your age. It’s that for every person who’s been summarily ignored because of their age – she went from 49 to 50, and then she became invisible. And then they threw it to the show hosts afterwards, and it was like, two middle aged white guys.

LJS: I can’t even remember.

EMK: This is the kicker. This is why I won the debate. The two middle aged white guys have their co-hosts kind of ribbing them. “Oh, yeah. Can’t you believe – it’s so unfortunate that some people think women have to lie about their age. You guys would date women your own age, right?” And they looked at each other like they saw ghosts, and it was like, thank you. You made my point.

LJS: Oh, my. You have got an incredible memory. I think you should be one of those memory experts. It’s like, that’s unbelievable that you can remember all that.

EMK: But, yeah, as I said, it was a big day for me. Not a big day for you.

LJS: We used to do so many of those. For all of you listening, as I was saying to Evan, whatever happened to The Early Show? I can’t even remember, but we used to do it a lot, and then it used to be a lot.

EMK: You were the editor of More, so you had a big platform to get the message out.

LJS: It was a lot of fun. So let’s talk about how to reinvent yourself, as a woman, when you’re out there and want to reinvent your love life. I’ve heard it a lot. I’ve heard it from a lot of people. I’ve heard it from friends, I’ve heard it from people in the club about how hard it is to do this. Everything is in the apps. I even hear from my 28-year-old children how difficult this is. So you’re the expert on there; let’s talk about what women need to know. And from your point of view, what can make this all go smoother? Because people do want it to work and it just seems like – what I feel so bad about because I haven’t had to do it is that everybody says it’s terrible and it’s awful and it’s hard, and it’s this and it’s that, and it doesn’t seem like there’s any alternative right now.

EMK: Yeah, it’s really unfortunate. Back when we first met, online dating, my first book was about online dating and it was the thing that people were embarrassed about doing.

LJS: Right.

EMK: My first book is called I Can’t Believe I’m Buying this Book. Now it’s gone so mainstream to be ubiquitous, and we’ve moved to dating apps on cell phones, which has basically exacerbated a problem. Previous problem was you couldn’t meet people in real life. You’re divorced, you’re living in the suburbs, you work in a small office with a few other women. Most of your friends are married. There’s very logistical reasons why online dating is a useful medium. But like anything that was designed to solve a problem, whether it’s social media or cell phones, it’s also created more of a problem. Now we’re basically on apps that are based exclusively on looks. So it’s infinite choice in the gamification of dating, and unless you are smoking hot, and most of us aren’t, we all sort of feel discarded. Men and women alike.

LJS: Yeah. And it’s interesting because that’s what my son says. When I said, what’s so bad about it? He said, what’s so bad about it is that one swipe away is something possibly better. And it’s almost like a candy shop. It’s almost like, just keep – the more you – so there’s no incentive to look beyond what the candy looks like on the outside. It may be terrible tasting inside, but you don’t get there.

EMK: Well, at least old-school dating sites, like or an okCupid had a written profile. You could email someone. So there was something resembling courtship. We had some information to work with. We took away the profile, we took away the email. So it’s a face; you swipe right, you match, you text, you meet. And so it’s basically blind dating. And everybody finds it soulless because it is. And that’s the irony, is everybody complains about it, but nobody really does anything different.

LJS: Right, and nobody’s created anything different. The young people I feel really bad for because they’re less experimental than the older people are, I find. The younger people, they tell me, what I say to my son is, “What if you were on a plane next to the love of your life? Can you talk?” “Oh, no, I can’t talk to her. I have to be introduced.” I’m like, “What? What are you talking about?” At least I think we can break some of those barriers. Or what are you finding? What are you finding with women and men that are older?

EMK: Most of my clients are older. I’m 51. I’ve been doing this for 20 years. My clientele has aged with me. So giving advice to 28 year olds is not really in my wheelhouse right now. I probably wouldn’t even bother. But I do feel the same that you do. I feel for them because they don’t know the world before the Internet and cell phones.

LJS: Right. exactly.

EMK: It’s funny you brought up the plane conversation, because a lot of my clients, one of their biggest problems is maybe because they were married for 25 years, maybe because their work puts them in a certain space of being businesswoman, entrepreneur, masculine energy, something like that. They get nervous about dates in a way that’s sort of surprising. Like, dating becomes a really big deal because it’s so foreign to them. And so, when they go on first dates and they’re nervous, “Oh, my God, I hope I don’t say something stupid. I hope he’s not a serial killer. I hope he doesn’t try to kiss me.” All these words going through their head, I say, pretend you’re sitting next to a stranger on an airplane, and it’s just the guy in 22B, and you’re asking if it’s business or pleasure and what book he’s reading. Take it down a notch. It’s not that scary. It’s just talking to a stranger. If you have a nice connection, there’ll be another date. If you don’t, it’s no big deal. You never worry about the stranger in 22B being your soulmate.

LJS: Very good. Interesting. Yeah, that’s very good. So talk to me about what the women that you work with say about dating today, and then let’s talk about the men, because I think women are also interested in what the men are thinking. Like, why is this so difficult? Why is it hard?

EMK: Yeah, I think you probably talk about it a bunch. We probably read the same news. This sort of decline in institutions, right? This sort of individualistic society, rather than something that’s communal, and everybody’s sort of choosing their own adventure. So we could layer a whole bunch of things onto it. We could go back to second wave feminism in the 70s, where women suddenly had education, had their own money, didn’t need a man to take care of them. A lot of people don’t have to be in bad marriages anymore. That’s a net positive. We could also talk about how women have outpaced men and still want men to be the way they were 50 years ago. And there’s an interesting conundrum in that “I have my own money. I have a master’s degree. I make six figures. But I want a man who’s got more.”

LJS: I’ve heard that, and I’ve said to friends, “Really? Like, can’t we go? How are you going to balance that out?” There aren’t enough up there. Right, right.

EMK: If you’re in the 95th percentile, you’ve already eliminated 95% of men as inherently unworthy. Men don’t date that way. Right. And so we have this thing. We want men to be stronger, smarter, more powerful –

LJS: Taller! It’s like, oh, these women who say to me, he has to be taller. I’m like, are you kidding me? 

EMK: He has to be every – he has to be you. But better. And without any of your flaws.

LJS: Right? Without any of your flaws.

EMK: There’s plenty written about that. Famously, Eli Finkel wrote a book called The All or Nothing Marriage. And he talks about what he calls Mount Maslow. Maslow’s hierarchy of needs. Right. We’ve reached a point today where it’s not just that he’s a nice guy, he has a decent job, he treats me well. He makes me laugh. He has to be a vegan, he has to be a downhill skier.

LJS: Oh, my goodness.

EMK: He has to have the same exact brand of politics that I do. He has to inspire me as a leader. We’ve placed so much on what one person has to be, we make it essentially impossible. And so we need to step back from that a little bit. Which is not to say that anybody should settle, but rather anybody who’s been in a happy marriage knows the important compromises one makes to be happily married. But you don’t spend too much time in your marriage wondering about the compromise. You compromise your way into happiness. If you’re doing it right.

LJS: And so give me a profile of the woman that you’re usually working with and how do you get her to where she needs to be? Give me some positive stories.

EMK: Oh, gosh. It’s probably asking you, Lesley, “Give me a story about being a journalist.”

LJS: Ah, okay. Pick one or two just so people understand.

EMK: Yeah, I’ve been giving dating and relationship advice for 20 years. I have a signature course called Love U that takes women from when they’re really at their lowest point – sad, lonely, confused, frustrated. “Why is this so uniquely hard for me?” We give confidence. We teach them how to date online. We teach them how to deal with dating multiple men. Sex, communication, intimacy, making better choices with men, because it’s usually the biggest problem people have, is not that there’s something wrong with them. They just have terrible taste in men. Like a GPS we try to lead you to better men. If you’re oriented for the loser, the liar, the slacker, the playboy, the commitment phobe, we try to steer you towards the kind of guys who have a chance of lasting, which will really change and revolutionize your dating experience. When you choose better men, the whole world opens up the same way that if you ate healthier food versus eating junk food, you’ll have a very different life experience. Over 20 years in steering women towards better men, we’ve got extraordinary successes. And women in wheelchairs, women who are blind, women who are in their 80s, women who live in rural parts of Alaska or Vermont, population two, who are happily married, started families. So my clients tend to range from late thirties. “I want to have a baby. Clock is ticking, I’m getting really anxious.” And then the majority are on the other side of it. They’ve been married and they stayed for ten years, 20 years, and are looking at their life and saying, “This can’t be it. I don’t want to be alone forever. It doesn’t have to be this way. But I don’t even know where to start.” And then I got a lot of clients. I’m doing a retreat with 12 women, average age is probably 65.

LJS: Oh, fabulous.

EMK: Yeah. I’ve never chosen my clients. They sort of chose me and I just do my best to give them all the unconditional love that they’ve lacked from men.

LJS: So what you’re saying is what’s going wrong is mostly it’s too many what? Too much tiny criteria that they put in terms of men. They have to have this, they have to be five-feet, ten and a half, they have to have blonde hair, they have to earn this. That’s what’s shrinking the pool piece of it. What else is shrinking it?

EMK: The bigger piece of it, and I was just writing about this yesterday on my Substack, was that so many people don’t have models for good relationships through no fault of their own. They grew up in families of dysfunction, alcoholism, divorce. Parents who didn’t really like each other stayed together for 40 years but didn’t model healthy relationships, and that becomes their picture of normal. And then you gravitate towards some form of that as an adult unconsciously and repeat that pattern over and over like touching a hot stove. Over and over. So we kind of have to rewire people to gravitate towards goodness and realize that a good relationship is not about anxiety or fear or “I’m afraid of expressing my opinion because he’s going to yell at me” or “I’m going to have to feel small in my relationship.” And you’ve heard these stories before. It’s not unusual. So it’s basically raising the bar for women. So there’s two things going on simultaneously. We could talk about hey, it’s okay if he’s five nine, not six-feet tall. It’s okay if you make more money. That’s a piece of it. But the bigger piece of it is good relationships are fundamentally easy. And if you’ve glorified, “Relationships take work and I’m going to stay even though I’m miserable, and I’m going to try to make him change and become the man that I’ve seen glimpses of in the first two months that we were dating.” If you’re going to spend your whole life bending over backwards to preserve a relationship with someone who doesn’t make you happy, you’re wasting your life. So it’s raising the bar for what women should expect from men and letting them know, yes, it is possible, but not if you keep on lowering your standards for men.

LJS: And then what are the men looking for at this stage? I think that’s one of the big questions that is kind of out there. Again, these are just stories that I hear, about guys looking at older women just for a one night stand, not really wanting to be in relationships, blah, blah, blah, blah. I mean, that’s just what I hear. I have no idea. But what are you finding that the men are interested in when they’re older? And why are they even on these apps? Well, I guess if they want a one night stand, they’re on the app. But is that really what they’re after? At that age?! Come on, haven’t we had enough one night stands by now?

EMK: I think that’s sort of like a false binary view of it, like a simplistic version of it. So there’s a term that my wife coined that I use liberally now: men look for sex and find love.

LJS: Oh, interesting. Very interesting.

EMK: Which, again, basically describes the behavior you’ve seen your whole life.

LJS: Right.

EMK: It’s not that they’re not interested in love. 80 million men are married in America, no one put a gun to their head. So men are looking for love. They’re just putting the sex part first, which is not something women necessarily do, so they’re initially surprised and disappointed. “Why does this guy look like he’s trying to get laid?” Well, he’s getting laid, and if he likes you platonically in addition to that, then he probably wants a relationship. So instead of taking that false binary view, let’s just assume that men, as opposed to being your antagonists who are there to torture you, are generally just as lost and lonely and confused as you are. And again, I use stereotypes to make cases; not everybody adheres to these stereotypes. I say that women, they’re not just looking for a man who’s taller, smarter, richer. They’re looking for a man unwittingly who makes them feel safe, heard, and understood,

LJS: I like those words. 

EMK: Yeah, I believe that to be true. Men may appear to be looking for someone who’s younger and thinner, but truly, he’s looking for a woman who makes him feel accepted, appreciated, and admired. And if you could be the woman who makes him feel accepted, appreciated, admired. If you’re the only person he’s ever met who says, you know what, I see your flaws, but I love you anyway, you will be the first. And that’s why he will want to commit. Every guy has broken up with someone who’s attractive. That’s not the thing they chase attractive. They stay because they feel good about themselves instead of constantly being told how much they suck.

LJS: Interesting. What are the other issues that you see when it comes to dating 40+?

EMK: The story is there’s no good men.

LJS: Yes, right, I’ve heard that.

EMK: Right? We always have to validate that story, because I’m not going to gaslight the people who are listening to this and suggest that everybody’s observations are wrong. I think they’re just a little simplistic and blunt. Let’s even go so far as to say that 90% of men are incapable of being the man that you want them to be. Right? Which doesn’t mean they’re – I mean, these are the men you’ve been dating, right? They appear to be cute, but they’re narcissists. Or they appear to have their act together, but they’re really avoidant commitment phobes. Or he seems really nice for the first month, but then he lets down his guard and it turns out that he’s really selfish. That’s part of dating. It’s the reveal. We can’t know from a guy’s dating profile who he is.

LJS: Right.

EMK: Let’s validate. Okay. 90% of men are not capable of being great long-term partners. So what does that leave? 10%. Well, you’re an Ivy League institution. You’re allowed to have high standards. Great. Let’s eliminate 90% of men. Just like 90% of jobs are not available to you either. It’s okay if you don’t want to do what 90% of people do, but if there’s 10% of the population who are decent men, who are capable of being good partners to you, let’s date within that 10%. And they’re just mixed in with everybody else online, you can’t tell. That’s what dating is about, is holding out for the possibility that you can get a top 10% guy, and then all you need is one.

LJS: Right. Yeah, that’s what I always say, all you need is one.

EMK: It’s the same as everything else. You don’t go into Macy’s and buy everything in the store. You find 90% of it’s not for you, and you walk out with a handful of items.

LJS: Right. So, are there any clues to – have you found over time? Like if this word or this phrase is in his profile, he’s somebody you should pursue or are there any sort of tips and tricks like that? There’s no fast route to anything, huh?

EMK: I think that’s the thing. Your question is – I really appreciate the question because it is the question women are asking. They’re looking for answers really quickly. And it does a disservice to the human being. Right. Especially on a dating app where you have like five photos and three one-line sentences. There’s nothing to it. So I’m going to try to read between the lines with his one sentence? It’s not really doable. So at the beginning, we’re kind of giving people a free pass. Is he cute enough? Does he seem intelligent and normal enough? All right, let’s talk to him. And it’s in the talking that he reveals himself. It’s in the courtship process from dating site to one month later when you both decide to take down your profiles and give a relationship a shot. And the way you determine whether a guy’s worth your time at the very beginning, right? First date: comfort, fun, attraction. If you get everything else out of your head, not dissecting him, “What’s this guy’s deal? I’m going to find out who he voted for in the last election. I’m going to find out if he’s got money in his 401K.” You don’t go in like an interrogator. But that’s what everybody’s worried about.

LJS: Oh, okay.

EMK: Everybody’s all in their head about, “Who is this guy? What’s his deal? How is he going to hurt me?” They’re trying to find red flags. And that is anathema to how to have a good connection with someone. Because it’s mostly fear based. “I’m trying to avoid the worst case scenario. And maybe if I ask you tough questions on the first date, you’ll fold.” So we really want to make a connection the way we talked about prior to this call, sitting next to a stranger on an airplane, having a pleasant conversation. Low stakes. And if, at the end of the date, you can evaluate him clearly: Comfort, fun., attraction. Positive scores, six and above, go on a second date. And if you’re not attracted to him, don’t go on a second date. And if you didn’t have fun, don’t go on a second date. And if you couldn’t really be yourself and you found yourself feeling awkward and nervous or you felt a bad vibe, don’t go out with him again. You don’t have to give guys a shot because he’s nice or cute or you’re lonely. So having better discernment about when a guy should keep moving forward will save you the trouble of being with a guy who is not a good partner for you for years at a time.

LJS: Now, let’s talk honestly. One of the things we know to be true: a lot of men don’t keep themselves up. Women are better at it in general. And they can’t help that they lose their hair. I hear this: “Oh, but he’s bald.” It’s like, well, he can’t help that. I mean, most of these guys are going to be bald. It’s not their fault. Can we get over that? How do we get over those things? And in general, the men just don’t. Just in general, in the population, women are more conscious. They take better care of themselves in general, and the men don’t. What do we do? How do you deal with that?

EMK: This is bigger than us, Lesley. We’re talking about big societal change. So I tend to traffic the world as it is, not how I want it to be. So is there a whole multibillion dollar beauty industry for women that every woman you know is somehow a part of and complicit in for the value of looking youthful? Yeah, that’s not something that we can legislate on a one to one basis. And are men overvalued for their work and their accomplishments by women? Yes. So women are overvalued for their beauty. Men are overvalued for their status and their wealth and their accomplishments. So that’s what we people double down. I didn’t create that. I don’t think it’s necessarily a good idea, because marrying a guy because he’s rich doesn’t have a great track record, or marrying a woman because she’s beautiful doesn’t have a great track record.

LJS: Right.

EMK: So I think that’s sort of fool’s gold. And it’s why if I were coaching men, I would be like, “Hey, stop venerating youth and beauty and date a woman your own age, dummy.” That’s what I would tell men. So we could say to women, “Hey, maybe the guy who has his own private island isn’t necessarily the best husband.” Sounds really fun, but I don’t know of any happy Mrs. Elon Musk or Mrs. Steve Jobs. I don’t think it exists. So maybe just a guy who helps around the house and listens to your emotional cues. Let’s start there.

LJS: Yeah. I’ve always felt that was – I like the word fool’s gold, but I’ve never really bought into that thing. I think you have to be very suspicious all the time.

EMK: I think it’s all about balance, right? Ruth Bader Ginsburg didn’t marry another supreme court justice. And Rupert Murdoch didn’t marry another billionaire. He just wanted a blonde 30 years younger.

LJS: Right. And it keeps going.

EMK: It’s okay to have balance. You don’t have to date your clone. You date your complement.

LJS: Date your complement. Okay. With that, let’s talk about where people can find you and what you’re going to be doing coming up shortly.

EMK: my name is Evan Marc Katz. I’m a dating coach for smart, strong, successful, high achieving women who have everything but the guy. I am everywhere on the Internet. You can find my podcasts at the Love U podcast on Apple, you could find me on Substack, a publication called Lovesplaining. I’ve got an Instagram channel, a YouTube channel, blah, blah, blah, blah, blah. I made a gift for your readers.

LJS: Oh, good.

EMK: If you go to I will give you a gift. It’s a 25-page PDF called “The Seven Massive Mistakes You’re Making in Dating.” You probably don’t even know they’re mistakes. That’s why they’re interesting. So I hope you read that. I hope it makes a difference to you, and I hope that if you decide that you need help, you could reach out to me, and I could get you the love that you deserve.

LJS: Oh, I love that. So, thank you so much, Evan. That’s great. And I think it’s wonderful. And you just have a wonderful memory. And I love the fact that you’re all in for these women, because it’s tough out there, and I want everybody to have what they’re looking for. Nobody should have to settle, and no one should have to be alone if they don’t want to be. So thank you so much for joining us.

EMK: Thank you so much for having me. I really appreciate it.


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