I hate to be such a cliché psychoanalyst, but there’s this thing called the Oedipus complex… My 52-year-old friend recently separated from her husband. So I made her a dating profile, and it made me realize something. The oldest age gap that I had was eight years, and she was 35 and I was 27-years-old. So I’m 34. The oldest I’ve been on a date with I want to say is close to 50. I am 28 years old and my ex-girlfriend was 42 and had two kids that were the same age as my siblings. More young men are seeking to date older women than ever before. I was really attracted to the level of emotional maturity that they could give me. Just the openness for relationship, a real relationship exclusivity, something longer lasting. They tend to be more in their careers, and they tend to be more peaceful when it comes to dating. The dating app Feeld reports huge growth in this area in just the past two years. Really because of a toxic dating world. All social media is men are trash. Who’s not saying that. The older ones up, they’re not ghosting me after six weeks. Women over 40 have more spending power and social capital than ever before. So is that why these new age gap relationships are all the rage. To find out, I spoke with writer and psychoanalyst Jamieson Webster and New York Magazine writer Emily Lebert. Thank you both so much for being here. Hi, Emily. Hello hi, Jamieson. We’re going to talk in, quite general stereotypes, because that’s the only way to talk about large groups of people by gender and age. And we’ve all been seeing this in film and television. There’s “Babygirl” You think I don’t like power. I think you like to be told what to do. The reality show “Age of Attraction.” I’m 5’ I am 27. There’s “The Idea of You.” I’m too old for you. There’s more than I can list over the past several years. And so I was also really curious of like is this actually happening in the world, not just in the media. And I reached out to the dating app Feeld, and I asked them to run numbers about this and was just like, are you seeing this data in your dating app. Data and they said that over the past two years, the number of men who are exclusively interested in dating women older than themselves has increased by 64 percent and that is particularly true among the youngest bracket of men, 18 to 25-year-old men. And so I’m just really curious. This is happening, and I’m really curious about why it’s happening now. Emily, you reported a whole story on this. So what were you expecting to find. What did you find. What surprised you in your reporting from the women that I spoke to in my reporting. And these are women across all ages. I think the biggest thing was a sense of freedom, that they’re not really beholden to this mold that men might have held them to before, that they can just simply be themselves, that they don’t have to pine for male validation and male desire, and instead men can just come to them like they wanted to find somebody who isn’t necessarily economically outearning them. They didn’t necessarily want to be with somebody who is more successful than them. They don’t care about those things. They just want to be in a relationship, a loving relationship with a partner who sees and respects them. I think the other thing is that they do get a sense of joy in being able to shape a young man. I think some of the women that I spoke to were very interested in building a boyfriend as of perfect product that they can carry on their arms a purse. I love how you or one of the women you spoke to called it a builder boyfriend, there’s a lot more sense of shaping it, and I’m curious a little bit more about what you were saying at first part of the pleasure is that men come to them, that they don’t have to be in pursuit. It’s reverses our image of the cougar, who is predatory for a lot of these women. Are they describing that they are being approached by these young men Yeah there was like a stampede of young men coming up to them in bars. Like one of the women was at a Times Square like random dive bar. And she was like, I could not even take a breath. I could not take a sip. Every 20s some 20 something was coming up to me. But I think that’s really exciting for them. Even if they are just in their late 20s or early seconds, to see that all of the work that they’ve put into their education and their personal finances, to see that being valued instead of purely just as a young woman, purely an object I think that is really cool for them. I love that. And Jamieson, are you seeing this happen either in your social life, in your practice. Are you seeing this happen around you, this kind of relationship. I’m not seeing it in any particular fashion. Personally, but I certainly have seen it pop up in the culture and have been thinking about it. And I think a lot of what I do hear about is dating fatigue with respect to the apps. And what’s being called the manosphere is something that I think kind of on everybody’s mind and what’s happening for men and their sense of possibility, which seems to be part of the story of this question of age gap relationships. One of the things that I think is shockingly more visible and present, especially in the lives of my patient, and that the apps highlight is just the feeling of the sheer number of other people and the ruthless competition in that, which isn’t helped in a society that doesn’t particularly that is increasing inequality rather than reducing inequality. So on the one hand, you have a situation which is increasingly unequal, and then you have a sense of just the sheer number of other people out there as a pool in which you’re competing with. And there’s something about this for men, including the fact that women and men are the equality is shifting. And it’s not great. It’s not where it should be. But there’s greater equality between men and women. And so there’s something about trying to find a place in which something of themselves feels like they have a leg up. And it seems like this age gap relationship is a place where they can feel that, especially as a very young man, where you haven’t proved your potential yet Yeah and so obviously, we do have double standards around how we perceive age gap relationships. And I’m curious why you think that is. And if you think that perhaps it’s seen as a bit more subversive or less predatory for older women to want to date younger men and why Yeah, from my perspective, I think that the intention matters deeply. I think what we’ve seen play out on reality TV a million times over is this idea of an older, wealthy man finds himself a very attractive young woman to procreate with and to have her look after the House. And guess what happens 30 years later, almost every time, he moves on to the younger model. But I think it comes back to well, what was the intent of that relationship. Did you just want somebody to crank out some children for you. And I think when we’re talking about older women dating younger men, a lot of the stories that I have heard often include women looking for an equal partner, somebody that maybe they aren’t on the same economic standing to begin with but who she’s hoping to nurture so that they can be on equal footing eventually. And I don’t think that is always or necessarily true with men. I made a profile, a dating profile, for a friend of mine who is in her early 50s, who recently got out of who recently separated from a very long marriage that she had entered quite young. And I was like, just watch. You’re about to be inundated with requests from young men. And she was like, why would that be. I don’t understand. Why would young men be interested in me. That makes no sense. And then as we were sitting there, as I set up the profile for her, it happened instantly. Like floods of requests from men in their early seconds. And she says this is still happening. And it’s very specifically men who are 35. And I feel so much glee for her. I feel really happy. I don’t know how much she’s going on these dates, but I just feel happy for her that she’s getting this attention, that she has this amount of possibility that if she wants to date men purely for their bodies, not that would be the only reason to date a younger man, but that she has this available to her. And I know that I would not feel this way if the genders were reversed. And so I’m just curious about thinking that through a little bit more. What do you think about it. Well, I don’t think that we previously were allowed to be outwardly horny we were not necessarily allowed to talk about our desires and the strangeness and singularity of them. So it does feel transgressive to be able to look at a dating app profile and really objectify very strong young man who’s maybe been tanning in Costa Rica for a bit. I’m just spitballing. So while that does feel fun, obviously we understand how really filthy and disgusting being objectified over and over again can feel. So again, it is imperfect. But I understand why that can feel like a nice power grab to sit there and be like what. I wasn’t afforded this privilege in the past. I am going to sit here and objectify the hell out of these 24-year-olds. Now, what do you think, Jamieson. Why are these women seeking relationships with younger men. What would you imagine they get from it. I guess I imagine that if there’s a caretaking element in terms build a boyfriend or curate the boyfriend, or help the boyfriend grow up, that it’s a relationship of care that also gets to be mixed with sexuality, rather than the necessity that a woman care for so much and take on all of the responsibility of care. So it’s care with a plus rather than the absolute negative that it is over time when it’s too much for a woman to handle. So a way of being sexualized for being caregiving rather than caregiving, being a desexualizing act. Yeah, yeah. I imagine that that’s important. And I also think that there must be a treatment of the anxieties that with the younger person, there’s somehow less anxiety. I don’t know if it’s that he’s less predatory or that he’s more dependent or that he’s more worshiping, but it must be treating anxiety of some kind. I wonder because I don’t know that I fully understand what you mean when you talk about the ways in which anxiety plays into sexual desire. And can you just say a little bit more about that. Like what. What do you mean by anxiety and how does that relate. I mean, I think anxiety is on the one hand about what it means to submit to the other person and to be dependent on them. So, I mean, part of what happens in relationships is that they are a playground for dependency, but they also become material dependencies in terms of how you put your lives together. And what that inevitably entails. And so I wonder what in these relationships treats it on both these levels. And obviously, the idea is that the man is willingly putting himself in a more dependent position with respect to the older woman and enjoying this. And what this does for her, I guess, is the question is, what is it for them to have someone who has this obvious dependency on them. How does that help them. And how much does this have to do with the economics, with women being more economically independent. I don’t because we’d have to find out if all of these relationships also have that class dimension in it. But I certainly think the fact that women have more economic independence and that the divorce rates are such that women are now used to in a way, trying to having to imagine or actually being in the position to raise a family on their own. And the fact that households require two incomes at this point really changes something such that you can ask a question about what kind of relationship that you would want as opposed to the one that you have to have. So it must be, I mean, it must be wild to just for women to be like, what do I want Yeah what did you find in your reporting about the economics of it all. I think that they were able to take career and that pure dollar sign out of things like if I were to take the finance bro out of finance, would I actually like who he is inside. And I think a lot of people would say maybe not sorry to the finance bros. So that ability to say I am going to center myself, center my career and my ambition and know that perhaps this person is dependent on me in that financial sense, but they are contributing around the House in different ways. Or they’re offering to get the groceries like it’s almost like the woman gets to step into that. Very “Mad Men” tropey sense of what it meant to be the provider. And I think that is refreshing Yeah I mean, I wonder also, I feel like in a lot of traditional heterosexual relationships, a woman who begins outearning her partner can be seen as very threatening. And I wonder if this is an antidote to that. I mean, again, all my references are reality TV, but we see this across Housewives franchises, seeing the woman through the platform of television becoming more and more successful or in other circumstances. And I have personal experience in this. I think that men are attracted to women with ambition and with careers until they understand what that means on a domestic level and how much time and access they have to. So yeah, I think the reality of that is very different. And if young men are down to be home more often and to wait for mommy to come home, then great, go for it. It’s so dependent on the male anxiety. I mean, in a funny way, we often think at best women actually don’t have anxiety. They just have anxiety about other people’s anxieties and how it’s going to set on them. And if it’s the male’s anxiety about not being powerful enough or needing to be really powerful or needing to be in a position in which he feels like he has a leg up and the woman’s just there, trying to manage all of these men’s castration anxiety and figure out, where a little sexual pleasure like, can come from in any of this. It’s the feeling you have. Totally but yeah, it does seem it does seem like the young men are of coming into these dynamics, accepting of the fact that they might always be in a beta role. They might always be the person who is cleaning up and not actually being the provider, as they were told this myth their entire life, that is their role. And that is their usefulness on earth. Absolutely. My producer reached out to a whole bunch of young men and asked them, why do you like dating older women. And there was a huge range of responses from people saying, I’m looking for maturity. There was a sense of maturity that I got from older women that I wasn’t getting with women my age. I’m looking for a relationship with more equality. To young men saying for younger women, they’re like all of social media is men are trash. Girls my age are, they’re [expletive] mean. They’re not nice. They want us to be earning more and they want our money. Not just me paying for things, not just going out to a bar and with an older woman. We don’t have those pressures. And does that speak to what you were saying before, Jamieson about the manosphere. How do you understand young men who feel that way. I mean, there’s so much anxiety in those tapes that you guys collected in terms of it’s just being parsed differently by them than the way that it had been previously. So, I mean, something about that is a tale as old as time, just in a new package. Image on the other hand, I see that the question of a woman’s desire, which is I think kind of what you were picking up on what a woman wants, which is what no man wants to deal with know. So they’re trying to find a way to deal with it. So before you dealt with it, by being a man who has the right to whatever woman he wants, and for her to be the mother to his children or to be his sexual object, or to be whatever it was, and that he could feel secure in that because the patriarchy helps him feel secure in that. Now that they don’t feel secure, they’re trying to find other means by which to have security. So we have a moment in which many, many things are shifting economically and politically and socially, and we don’t know where we’re going. We don’t know where this is going to land. And I think what’s going to happen is that there’s going to be a lot of experiments and intimacy. But I think we have to be careful of the old wine in New bottles. How do you think people react to these relationships between older women and younger men. How do you see it being perceived in the world, I think speaking back to that double standard that we spoke about initially, there is a huge amount of sexism that we see towards older men dating younger women. But the difference, again, is that women are taking back power. And even if it is imperfect, even if it is a small amount of power, it is something to them. And I don’t think it’s necessarily up to us to sit here and tell a woman how much power she does or does not have in her relationship or in her sex life. Like the reality is, while many of these women are saying that they’re having amazing sex, and I am very, very happy for them, we’re not in those bedrooms and we don’t know what dynamics are playing out and how they are testing the waters of that. Another thing that I think is really interesting is that I think we have to take into account aesthetics and beautification because women are getting facelifts at 35, 40, 45 years old. It is possible to technically look young forever. And in that sense, I don’t think outwardly there is as much taboo because you could technically look very similar age to a 25-year-old or 28-year-old. But again, that points out the inherent sexism in that you should be able to date whoever you want. And why are we judging older women for dating throughout the aging spectrum. We got this data from the Kinsey Institute that one in five young, straight men regularly fantasize about older women, and the reverse is also true. 64 percent of Gen X women say they fantasized at least once about being with a younger man. And in 2025, on Pornhub, a website that is primarily used by many people but primarily used, I think their biggest demographic is younger men. Search terms like cougar or 50 plus have risen by. I think cougar 8.5 percent 50 plus 105 percent How do you think the fantasy element of this plays into it? I mean, I guess I hate to be such a cliche psychoanalyst, but there’s this thing called the Oedipus complex. That Freud talked about once upon a time, and again, it’s this idea that ideas that we have about love and intimacy and sexuality and excitement are born at home, and they’re born in the familial relationship, and children feel incredibly sexually towards their parents. And then this goes into repression. And then it’s only supposed to color your relationship with not maternal or paternal figure or something. And behold, repressions aren’t always so sturdy. And so, I think incestuous fantasies have always been a part of sexuality. And so the interesting thing for me is like, why is this thing that’s supposed to be repressed and displaced wide out in the open. And what’s going on. What do you think. What’s going on with that. I think that it’s a sign of the decline of civilization, to be honest. I mean, that’s what Freud said, is that civilization is dependent on the prohibition against incest. It’s like you separate the generations and you send the person out on their own as an independent person to rediscover sex and love for themselves. And if our needs aren’t being met, or if repressions aren’t holding in some way, shape, or form, then there’s something wrong. I think in the tape that we heard, I think the first young man was talking about, he thought, younger women are mean and older women are like, come here, honey. The older ones up there, they’re like, come on, I got snacks right here. I got a juice box and some crackers just for you, big guy. Come tell me your feelings, I care. You are exactly describing. This is still that MILF idea of mommy’s going to take care of you now. It’s just happening in a different direction. Before it was women emotionally caretaking older men who had not worked out how to use or understand their emotions and communicate them. Now it’s in the other direction. Like it’s just mothering a young man into adulthood. And is that progressive. Is that empowering. I’m not sure. I wonder how much of it. I mean, I fully buy what you guys are saying, and I also wonder how much of it can be attributed to a liberation of female sexual desire and an ability to be doing, to be following that desire more purely when one has more economic independence. There was another study in 2025 published in the National Academy of Sciences journal, where they asked people if they were comfortable dating older or younger, if they wanted to date older or younger, and most women said they did not want to date younger, but then they made those same people do blind dating and women, both women and men, when they were actually blind dating, tended to prefer slightly younger partners. So women’s stated preference to which age they wanted to date did not match to their actual preference once they were dating. And how much of that is not. I mean, is about just younger bodies are more fit, more beautiful and this is women just being able to be purely driven by sexual desire. I interviewed Kathy Griffin at the end of last year, and she wrote this very sprawling, long Substack post about falling in love with a 23-year-old. And I think she’s in her 60s. She was very explicit about the fact that the best part of the relationship was their sexual relationship. And she said that she had found with him and other younger men that she had dated, that they were far more interested in giving than taking. And in that sense, I imagine for someone of Kathy’s age, that must be such a massive flip of the script for younger women, not so much, because they’ve been raised with a more sprawling sexual education. They know what it means to be able to come in multiple ways, to be able to express their desire to ask if they can receive pleasure first. I think that is sadly, somewhat New. I mean, how much of this is about a version of feminism, which is simply about saying women should be able to replicate all the behavior men do, including the behavior that we look that we stigmatize men for viewing. Is that part of what this is like. Is this the end goal of feminism that women, should also be able to be women should be like men. Yes, exactly. I just hope for something else than that. As a feminist personally. Well, what, talk more about that. I don’t know. I think that I just as an analyst and listening to people’s sexuality, reproduction, intimacy and care are really fraught. And we’ve had a greatly unequal society that has been what has scripted these for us. And so when we talk about freedom and choices and being able to be comfortable sexually in our lives, with partners, we just have. So we have such a long way to go. And to just merely flip the script is to me, point A when we need to get to point C. That makes so much sense. What do you think, Emily. Is the end goal of feminism that women should just be able to act like men. No, because men have historically been very coercive and been pillaging through communities. So, no, I don’t think the goal should be to act like men. I think that we deserve to hope for more than that. Like in a perfect matriarchal society, women do not want to be overlords. We don’t want to tell people how to live. We just want to be able to live freely and to give that right and that privilege to anyone who walks the earth. But where do we still. I mean, I’m going to use this word problematic, but when does an age gap get problematic. I think maybe and we can totally disagree, but I think we would agree that a 40-year-old man dating a 20-year-old woman feels uncomfortable because of the power dynamic between them. Does a 40-year-old woman dating a 20-year-old man feel just as uncomfortable in exactly the same way Yeah. Which isn’t to prohibit it. It’s not to prohibit it, but to say that there’s something uncomfortable about the recognition of the inequality by virtue of whatever, 20 years 20 years is a long time. And if you think of who you were when you were 20. And you think of who you were when you were 40, it’s mind boggling what those differences 20 years makes. And for a long time, we haven’t been able to say that a 20-year-old woman dating a 40-year-old man is insane. We say it now. Why wouldn’t we say it in reverse. But I mean something about recognizing time and that you also the asymmetry is such that the 20-year-old man has no idea what he doesn’t understand about being 40. A 40-year-old woman must understand something about what it is to be 20, even though she was never obviously a 20-year-old boy, but she was a 20-year-old girl. And so what is that in the relationship. I don’t know. I mean, that’s between them, but yeah, I mean, I understand I’ve dated people who were older and I’ve always felt like we were like I was very mature and we were very equal. And you don’t know what you don’t know. Simply don’t know what you don’t know. When I’ve hit the age that they were when we met, I’ve been like, what were they thinking. I was really young. I hadn’t even graduated from college. I was probably very annoying to date. And I wonder, do you think that it’s possible to be in an age gap relationship that doesn’t have a power imbalance. And for the sake of argument, let’s talk about a relationship that has at least a 10 year difference. Is it possible in that kind of a relationship to be fully equal. I was going to say no, but I think I’m going to change my answer. I don’t know if you’ve read the novel “Luster” by Raven Leilani. There’s this particular passage. She is a younger woman dating an older married man. The married man has opened his marriage and drama ensues. She talks about how the mere passage of years does not necessarily give anyone more wisdom, more creativity, more passion. Like there is a scenario in which dating an older man is simply just dating an older man, and maybe he is useless. But yeah, I think again, we’re trying to even the score of an imperfect system. And if we’re netting out at an older woman, is trying to get to the potential power that an older man might have a relationship. I just don’t know if that’s what we want. It’s like squaring the circle. It’s like a cursed game, right? I mean, I think that you can’t unilaterally say no, that just because there’s an age gap, there can’t be equality. I think the question would be how they negotiate it, how open they are about it, how much they have a capacity to confront what it’s about, and also the faces that a relationship is going to have to inevitably go through. Because what happens when I don’t know you’re 60 and they’re 90. I want to end with a segment called coinage. Basically, words like cougar field, predatory MILF feels explicitly sexual. This phenomenon is happening, but we don’t have language for it, and I wonder if you might be willing to propose new language. Oh, I thought of adulting. Adulting adulting to mean to mean dating an older woman Yeah, you’re trying to adult. You’re adulting. But this is what my son says when he’s like that he did his errands, that he was adulting. And I have to really question what he means by having done his errands. Yes, that’s right. It is hard, though. It’s hard. Yeah O.K, so my first instinct was something about the nannies or the babysitters because ideally, you would be mothering them, but it’s temporary. You’re mothering them into adulthood. But then I was like, well, that’s not helpful for us. Then I was thinking, what if it was like instead of milf? Then they’re like preppers, women I’d like to date, just “WILD” “wild things,” “wild-ing in,” “wild-ing out.” I love that, I was going to propose. I mean, this has been true. These kinds of age gap relationships have been true in queer communities for a long time. And in gay male culture, it’s daddies and twinks. So I was thinking mommies and minnows mommy’s a minnow magnet. Look at that mommy at the bar. She’s being surrounded by minnows. I thought that might work. That draws a very sharp visual that I think feels spiritually correct. Thank you both so much for being here. Thank you. This was really a pleasure to talk about this with you. You too.