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Narrator
What you are about to hear is a classic. Esther calling. A one time intervention phone call recorded remotely from two points somewhere in the world.
Caller
Hi, Esther. I'm pushing 40. I turned 40 in about six months. And to this day I've never had a relationship that's gone beyond four or five months. At first, like in my 20s, 30s, I thought, this is cool, just kind of drifting through life, coasting about. It's all good. But lately, over the last few years, it's really begun to concern me. Especially as I begin to feel that I actually want a relationship. Three, four months into the relationship, whatever, I just hit this wall. I get anxious, I begin to withdraw. She will basically call me out at some point and eventually the relationship will just end because I just can't communicate what is that I'm going through. I don't know what's making me anxious. I don't know what to do. Why can't I get past this point of a relationship? And it's really upsetting to me.
Caller (Esther's client)
Thank you.
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Caller (Esther's client)
Hi.
Esther Perel
Hello. Hello, this is Esther. And hello. I read and listened to your message, but ask me your question again.
Caller (Esther's client)
Well, I guess the question is, as I'm. As I'm pushing 14 in about six months, I do find myself growing increasingly concerned that I still to this day haven't had a relationship that's gone beyond four, maybe five months. So the question is, why is that? Why am I unable to. I mean, should I be concerned?
Esther Perel
And you mean all relationships? You mean romantic relationships? Friendships as well.
Caller (Esther's client)
I'm talking strictly romantic. Relationships? Yeah.
Esther Perel
You have long standing friendships.
Caller (Esther's client)
Yeah, definitely. Great friendships. I have friends who I've been with for. Who have been best friends for well over two decades.
Esther Perel
And can I just ask out of curiosity, do you ever wonder how come I can have these wonderfully long lasting friendships and I don't freeze and I don't shut down and I don't run away? You know, what's different?
Caller (Esther's client)
I mean, I do ask myself. Absolutely. And I guess the simplest way of putting it is I just feel I can't be my authentic self in a romantic relationship. My friends have commented quite often how I can be very charming off the bat and, you know, if I like someone, I'll just, you know, act on that. But within. Within a few months. Yeah. You know, I lose all interest or maybe they do and I get super anxious. It's one or the other. And I look back on those relationships and I feel that I was unable to be my authentic self. I just wasn't being me.
Esther Perel
I was putting on constantly because I was protecting myself. Against what?
Caller (Esther's client)
Oh, yeah. Against judgment, against being seen as boring or miserable or a project they have to take on. You know, God forbid I say how I'm actually feeling about this and the other, I don't want to be judged for it. And I do feel like I have to show the sunnier side.
Esther Perel
And what. How does it manifest?
Caller (Esther's client)
You mean within the relationship or. Well, like I say, it's usually one of two things. It's either me constantly being anxious that they're not into me as much as I want them to be. And I just desperately try to figure out a way to get them to like me and to come across cool. And I've become very latchy and they're quite needy. And I've definitely chased a few people off as a result. So they've just, in one way or another, they just basically dumped me in whatever way they do that. Ghosting, whatever. The flip side, I become passive and I withdraw. I no longer look forward to seeing them like I can't really be bothered. And I begin to resent. Resent them for. For whatever things. Oh. And of course, I guess the main thing is I lose interest in sex. I literally can't have sex with them anymore, which makes me feel terribly guilty because they get worried, they think it's them. I assure them it's not them, but then they want to know, what is it? I don't have an answer. It just gets worse and worse and worse.
Esther Perel
So, yeah, I mean, you're doing a beautiful job at describing it. Right. I either become the pursuer and I become needy and I depend on them and I want their attention but I don't feel that I deserve it, that I'm lovable, that I'm worthy of it. And so I start to feel very small and they feel very big. And I push them away because I come on so hungry and on the other side I withdraw and I'm the one who becomes passive. No, I don't ghost them. I just make it so that they end up leaving. Because it's so uninteresting. Because I give.
Caller (Esther's client)
Exactly.
Esther Perel
And I become avoidant and. Yes. And sexual disinterest and probably matched by sexual lack of performance. Go along with that. So that I make the point in multiple ways and neither of them is what I want. And I suppose you're telling me I don't really know where this comes from or why this becomes so intense. But the nice thing by turning 40 is that I finally begin to realize that this is me and that this list goes with me. And that the pattern has repeated itself enough times that I now know that it is not. Because there's something missing in the other person.
Caller (Esther's client)
Exactly right.
Esther Perel
Which is what you probably thought for the first 10 years.
Caller (Esther's client)
Yeah, yeah.
Esther Perel
You know, the constant factor here is me. And maybe I should take a look at myself and what happens to me that I become so either immersed and at the mercy of or fleeing because overwhelmed. And both are actually fears of. You know, they're the same fear from two sides. They're not that different. They manifest one in the pursuit and the other in the withdrawal. But they're actually two sides of the same fear and of the same struggle you have around your attachment to these people. And why not with friends? Because for some reason the only relationships that mirror each other are the ones that we have with our early caregivers or parents and the ones that we have with our romantic partners. Somehow we manage to not repeat that when we have with our friends so many times. People say, but I have long standing friendships. Why don't I get that there? Because the stakes never feel that high. I never feel like my sense of lovability and self worth is on the line in this way. So tell me a little bit about the early relationships that you had with your caregivers or parents. Who was in your life, who was there for you, who was not there for you?
Caller (Esther's client)
So my parents got divorced when I was 12, 13. It was a terrible divorce. Just an absolute car crash.
Esther Perel
In what sense?
Caller (Esther's client)
My father was under immense pressure from a new business venture that was going wrong. He was getting very stressed out. Basically they decided to separate because there was just too much arguing at home. And then my mum went to see him one day, I think it was a morning. And I only discovered what actually happened years later. But what happened was she discovered him in bed with another woman and then came home in bits, which I remember vividly. So a four person household became three. Me, my mum, my sister, just like that. And my father's always been around. We have a close relationship. At least now we do. Wasn't always that way.
Esther Perel
You're number one or number two?
Caller (Esther's client)
I'm number two. I'm the youngest brother. Yeah. And we saw him kind of like on a weekend basis. And I remember there were really staid affairs when he would just take me and my sister out for lunches, for coffees. You know, he's making an effort to obviously keep in touch, which is great. But they, as I look back, they were very awkward, uncomfortable affairs because he never once even to this day talked about what the fuck happened. He never. He did you ask. So my sister was the. Was the vocal one. She kind of. She was sort of the campaigner on both of our. Perhaps she was one who would like to try and ask and try and understand. And my role was passive. I would just sit there. The few times my sister did try to bring it up, I would just sit there and just watch them kind of having it. Have it out. But, you know, that was 20 years ago. We both come a long way since and have a great relationship with them now.
Esther Perel
But you still haven't asked a question.
Caller (Esther's client)
I don't think I once asked or have asked him ever what happened? No, literally, not once.
Esther Perel
So I think it's more than just what happened. I think that there's a conversation with your dad about, you know, dad, this story that went on 20 years back, it still has a hold on my life. I feel lonely. Have been trying to understand how that impacted me, what that did to me. And I would love for us to have a chance to talk about this. This is not a recrimination. This is not a blame session. I just need to understand because here I am close to 40, I finally switched from thinking about all what was missing in the women I was meeting to realizing that the story was inside of me.
Caller (Esther's client)
Yeah, yeah.
Esther Perel
What, what makes you laugh?
Caller (Esther's client)
I always laugh when I get nervous.
Esther Perel
Okay. It's good.
Caller (Esther's client)
Yeah. I'm terrible with these feelings. I'm always laughing.
Esther Perel
We have to take a brief break, so stay with us and let's see where this goes.
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Esther Perel
My guess, I may be completely off here, but my sense is that you tell me when you withdraw, which one is the story that replaced your mother and which one replace your dad? The withdrawal or the pursuit?
Caller (Esther's client)
As in, which one is my mother? This or the other? Is that what you mean?
Esther Perel
Yeah. When you hold on and you become all needy, dependent and please, please. When you cling, which story do you replay? When you cling and which story do you replay when you flee?
Caller (Esther's client)
Well, my feeling is that when I'm clinging, that's definitely me replaying, trying to get validation from my dad. And it was my mum who pointed out to me that until recently anyway, the women that I seem most drawn to were the stern ones. And I didn't see this. I did not see this common thing. And it just made. And it just hit me hard, like it made total sense. She was right. So I feel that's. That's my dad. I guess if my mom. I don't know why it's harder to talk about my mom, I guess. My mom and I are very close. I haven't really thought about it like that, but I guess.
Esther Perel
What is the feeling that makes you withdraw? You start to withdraw when. And you lose sexual interest When?
Caller (Esther's client)
Yeah, when I feel trapped.
Esther Perel
When I feel contained and I feel trapped and contained. When I feel. That's not a feeling, by the way. Trapped and content. What is the feeling when you feel trapped and contained?
Caller (Esther's client)
Scared. I feel scared. And I'm scared of being seen for all my ridiculous ugliness, is what it is. Being seen for this mess who hasn't got a effing clue what he's doing, who is. Who is sad quite a lot of the times, actually. Fuck, I mean, angry. Constantly angry. I feel it. I feel. And I'm just worried about being seen as a bit of a head case, Being seen as unsure of himself and uncertain and weak and all that.
Esther Perel
Yeah. A human being, basically.
Caller (Esther's client)
Yeah.
Esther Perel
Tell me something, R. What happened to your mom after your dad left?
Caller (Esther's client)
Okay. My mum was miserable for a long time. She was fucking angry and resentful and that bastard this and how can he that. And, you know, I recall her being directly looking at me and telling me I have to do something about it. I can't remember to this day what she needed me to do exactly, but she was telling me, like, I have to do something about this because he's not doing this and he's not doing that. And I felt like I never measured up to whatever it is I was supposed to do to help her. And she was just on the edge. She had breakdowns and I.
Esther Perel
And I felt trapped.
Caller (Esther's client)
I felt trapped. Yeah. And I got angry at her. I was behaving like a brat. I was behaving like a little shit who didn't want to know about her misery. And I hated that sense, you know, I hated it when I come home from school and she's anything but happy. And I just want to put distance between myself and that, you know, I don't want to know because it. It's too close to the fucking pain, you know, I don't want to know that shit. And I just didn't want to know.
Esther Perel
Tell me.
Caller (Esther's client)
And it made me angry.
Esther Perel
Don't laugh when you want to cry.
Caller (Esther's client)
I can't help it.
Esther Perel
Because you went through a lot and you were a 12 year old with your mom and your sister and you felt at the same time terrible for your mom and at the same time you wanted her to stop feeling terrible, period. And you were overwhelmed and you couldn't get her out of it. And every time you meet a woman now and you start to feel responsible for her and you start to feel close enough to know how she feels, the entrapment fear comes right back. And what better way to flee and to reenact it also then to lose instant sexual interest.
Caller (Esther's client)
Yeah, it's the quickest way. Yeah.
Esther Perel
So here you are with your mom, who is basically taking up a lot of the space with her experience and her sadness and her rage and her drama. And you don't know what to do because it's too much for a little boy to be able to make his mommy happy the way he was hoping that she would be. Because if she was happy, then he didn't have to worry. And then he could actually think about his own life. And so becoming a brat and a shit is the way that a teenager tries to create a boundary so that he can deal with his own life. And he pretends he doesn't care, but in fact he cares so much.
Caller (Esther's client)
Yeah. Yeah. It's just so. Just sounds so obvious when you say it this way.
Esther Perel
This is new to you.
Caller (Esther's client)
Some of it is new to me. It seems very obvious, but I've never heard it really put back to me that way before.
Narrator
We'll be back with a session right after this, and while we love our sponsors, if you want to listen to this session ad free, click the Try Free button to subscribe to Astera's office hours on Apple Podcasts.
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Esther Perel
What's the thing that touches you the most.
Caller (Esther's client)
You said responsibility and this sense of fleeing and that really. Yeah, because the thing you said about how I just want to make my own boundaries, I want my own life, actually, I don't want anything to do with this shit. But at the same time, I do care deeply and it's that kind of tussle. And that's exactly it. That's exactly it. And when you said that translates to fleeing, I feel that.
Esther Perel
Yeah, yeah. You don't flee because you don't care. You don't flee because you're cold. You flee because you don't know how to get close without instantly feeling the burden of caretaking and responsibility.
Caller (Esther's client)
Yeah. Mm.
Esther Perel
Where does that reach you?
Caller (Esther's client)
It's. I. I don't know how to ask the question to. Honestly.
Esther Perel
It's okay. It's okay. Yeah, you can let it sit.
Caller (Esther's client)
But I'm kind of thinking, yeah, I'm just sort of like nodding to myself like, yeah, yeah, I know one that I was so angry and I still get angry at her. I honest to God, sometimes it's so. I feel so ashamed of it afterwards. But I can regret as a 39 year old man, I can regress like that back into my childhood state. Just like a click of a finger and I am shouting at her. And I just feel so ashamed that because it's your mom and because you.
Esther Perel
Don'T know of another way at this point to create some distance or some separateness so that you. Without having to have a yelling match. And so it feels very regressive, it feels very young, you know, because part of you doesn't know how to be close without also feeling the burden of responsibility. And that happens with her and that happens with the women. And that's why she's perceptive that you may be going out with more stern women or more aloof women, because I think your romantic unconscious thinks that these women will be less needy and you won't have to be so responsible for them, which may not always be the case. And that's not always the case. But that's how it appears at the beginning.
Caller (Esther's client)
No, that is so spot on. I just came out of a relationship very recently and again, surprise, surprise, four months thereabouts. And the funny thing is this person was quite offish to begin with and a bit stern, a bit dismissive, and it just drove me wild and I had to get to the bottom of this and then I won this person over. But then once they kind of came into the fold, as it were, and we actually began to this great time together. It didn't take long for me to do the opposite. And then them expressing their closeness with me and I began to withdraw.
Esther Perel
Yeah.
Caller (Esther's client)
And this person saying, what the hell is wrong with you? Because you're the one who was chasing me.
Esther Perel
Yep.
Caller (Esther's client)
Mr. You know, like what the hell? And I don't know what to say. I'm just, I'm just like hands up. Yeah. I don't know. I don't know what just happened there.
Esther Perel
Well, what just happened is that there's an overlap and it's easier to pursue someone who is holding back because then they don't overwhelm you. And there is no reenactment of this dance that you have with your mom. And what will help you hopefully have different relationships in your adult life is when you are able to disentangle and when you see it happening, that's when you're going to have conversations inside of you between the 12 year old and the adult. Because some of this is fiction. Meaning these women don't maybe need the kind of responsibility that you think, think they do. But you get this entire internal world activated at that moment. And it's about closing the gap between the 12 year old and the 40 year old when it comes to closeness.
Caller (Esther's client)
I just can't believe how accurate that feels. I've. Without diminishing the work of my therapist, who's a wonderful, wonderful therapist, the reason I went to this person the first place is pretty much for this thing. And I feel like this is it. Like it just, this is it. I mean, I actually feel good about this because it's, it's like a massive knot has come undone and it's caused me so much distress and anger and sleepless nights and just being so fed up with myself for so long. And I just can't believe you're able to articulate it like just, that's what it is.
Esther Perel
We have articulated it. We have not. I, we have articulated it.
Caller (Esther's client)
Sure, sure.
Esther Perel
Because if it, if it hits the spot is because you're right there already. I could have said this to you 10 years ago and it would land on deaf ears. So it's always a meeting between what I say and what you're able to hear. And so that to me says that the gap is beginning to close. You could even go back to the woman you just left and just say, I had a real reckoning and I understood something and I owe you an apology. If you're still interested.
Caller (Esther's client)
I can, I mean, we're still in touch. After all that she'd be very receptive.
Esther Perel
To it, I feel. She would be. Yeah. So that's just. That's the more you bring that to her and you ground the experience with her in the present and then you say, look, I'm just beginning to disentangle this, but I know this had nothing to do with you. Here is what I've understood in the meantime, and if you choose that path, let me know. I'm very curious where that would go.
Caller (Esther's client)
If I reach out to her. Yeah, okay. I probably will do that. That for me would be a lot easier than the one about my dad, but I'll definitely.
Esther Perel
Oh, yeah, I'm putting that one in the deck as well. But I'm going to leave you there.
Caller (Esther's client)
Sure. Esther, thank you so much.
Esther Perel
You're welcome. Thank you so much.
Caller (Esther's client)
I'm so grateful.
Esther Perel
My pleasure. Bye. Bye.
Caller (Esther's client)
Take care.
Narrator
This was a classic Esther calling. A one time intervention phone call recorded remotely from two points somewhere in the world. If you have a question you'd like to explain Floor with Estaire that could be answered in a 40 or 50 minute phone call, send her a voice message and Esther might just call you. Send your questions to producerstairperrell.com where should we begin with Esther Perel is produced by Magnificent Noise. We're part of the Vox Media podcast network in partnership with New York Magazine and the Cut. Our production staff includes Eric Newsom, Destry Sibley, Sabrina Farhey, Kristin Muller and Julian at Original music and additional production by Paul Schneider. And the executive producers of Where Should We Begin are Esther Perel and Jessie Baker. We'd also like to thank Courtney Hamilton, Mary Alice Miller and Jack Saul.
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Episode: Esther Calling – Still Single at 40
Release Date: August 25, 2025
In this one-time intervention call, Esther Perel engages with a 39-year-old man who is deeply concerned that, despite having strong, long-standing friendships, he’s never managed a romantic relationship lasting more than four or five months. Approaching 40, he’s anxious about repeated patterns—either feeling needy and anxious or withdrawn and uninterested. Esther guides him in exploring the origins of these patterns, particularly his family dynamics after a traumatic parental divorce, and how those early experiences shape his current relationship fears and behaviors.
His mother’s pain and the expectation that he “do something about it” left him feeling trapped and resentful, sometimes reacting with anger or emotional distance.
Esther’s Summary: His withdrawal from intimacy echoes his teenage rebellion—anger and distance as an attempt to create boundaries amid overwhelming maternal need.
Esther’s Guidance: Greater self-awareness enables him to navigate current relationships differently by distinguishing past triggers from present reality.
Empowering the Caller: Encouraged to be honest with former partners about these revelations.
This is a warm yet unflinchingly honest conversation in classic Esther Perel style—curious, empathic, and direct. Both participants move from confusion to clarity. Esther gently identifies the emotional inheritance of romantic struggles and provides a path toward meaningful change—grounded in courageous self-examination and honest communication.
Summary prepared for listeners who wish to reflect on relationship dynamics, attachment history, and the transformative power of insight in personal growth.