Still Single at 40

In this classic Esther Calling, Esther meets a man who’s never been in a relationship for more than five months. As he approaches age 40, he knows the reason lies with him, and not the women he’s dating. Esther encourages him to look back and see if the clues can be found in his early parental relationships. Perhaps the work starts there. Esther Callings are a one time, 45-60 minute interventional phone call with Esther. They are edited for time, clarity, and anonymity. If you have a question you would like to talk through with Esther, send a voice memo to [email protected]. Want to learn more? Receive monthly insights, musings, and recommendations to improve your relational intelligence via email from Esther: https://www.estherperel.com/newsletter Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Speaker 00

  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.

• 0:12Speaker 01

  Hi Esther, I'm pushing 40. I turn 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 twenties, thirties, 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.

• 0:52Speaker 01

  And eventually, the relationship will just end because I just can't communicate what is and 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. Thank you.

• 1:23Speaker 02

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• 2:08Speaker 03

  Support for the show comes from TikTok. There is a scientifically documented correlation between listening to podcasts and curiosity. So since you're here, you probably enjoy discovering new things. One great place to indulge your curiosity is TikTok. Whether it's how to forecast volcanic eruptions, strange phenomena that the James Webb Space Telescope picked up near the beginning of time, or a literal deep dive on the ocean's deepest reefs. TikTok has a wealth of fascinating videos just waiting to be discovered. Your next discovery is waiting on TikTok. Learn more at tiktok.com/discovermore.

• 3:02Speaker 04

  Hi.

• 3:02Esther Perel?

  Hello, hello. This is Esther and.

• 3:06Speaker 04

  Hello.

• 3:08Esther Perel?

  I read and listened to your message, but ask me your question again.

• 3:16Speaker 04

  Well, I guess the question is, 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?

• 3:40Esther Perel?

  And you mean all relationships? You mean romantic relationships, friendships as well?

• 3:45Speaker 04

  I'm talking strictly romantic relationships, yeah.

• 3:48Esther Perel?

  You have longstanding friendships?

• 3:50Speaker 04

  Yeah, definitely. Great friendships. I have friends who I've been with for, who have been best friends for well over two decades.

• 3:58Esther 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?

• 4:18Speaker 04

  I, I mean, I I I do ask myself, uh, well, 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, add on that. But um, within, within a few months, yeah, you know, I I I lose all interest. Or maybe they do, and I get super anxious. It's one or the other. And 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. I was putting on constantly.

• 4:58Esther Perel?

  Because I was protecting myself against what?

• 5:02Speaker 04

  Oh, yeah, uh, against judgment, against being seen as boring or miserable or a a project they have to take on. You know, God forbid I I say how I'm actually feeling about this and the other. Um, I don't want to be judged for it, and I do feel like I have to show the sunny side.

• 5:19Esther Perel?

  And what, how does it manifest?

• 5:21Speaker 04

  You mean within the relationship or?

• 5:23Esther Perel?

  Mm hmm, mm hmm.

• 5:24Speaker 04

  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 um, I just desperately try to figure out a way to get them to like me and and to come across cool and I've become very latchy, you know, quite needy, and I've definitely chased a few people off as a result. So they've just in one way or or another, they just basically dumped me in in whatever way they they do that, ghosting, whatever. Or the or the flip side, um, I become passive and I withdraw. I no longer look forwards to seeing them. I can't I can't really be bothered.

• 6:06Speaker 04

  And I begin to resent resent them for for for whatever things. Um, oh, and and and of course, I guess the main thing is, um, I lose interest in sex. I I 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 I 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. So, yeah.

• 6:31Esther Perel?

  When 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.

• 6:56Esther Perel?

  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 them nothing. 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 forty is that I finally begin to realize that this is me, and that this list goes with me,

• 7:40Esther Perel?

  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.

• 7:48Speaker 04

  Exactly.

• 7:49Esther Perel?

  Right, which is what you probably thought for the first ten years.

• 7:53Speaker 04

  Yeah, yeah.

• 7:55Esther Perel?

  Right. 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,

• 8:38Esther Perel?

  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.

• 8:58Esther Perel?

  So many times people say, but I have longstanding 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 underlined 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?

• 9:25Speaker 04

  Okay, um, so my parents got divorced when I was uh twelve, thirteen. Um, it was a terrible divorce, just an absolute car crash and.

• 9:36Esther Perel?

  In what, in what sense?

• 9:39Speaker 04

  My, my father was under immense pressure from a new business venture that was going wrong. He was getting very stressed out. Um, basically, they, and they decided to separate. Cause they just, there was just too much arguing at home. And then my mom went to see him one day, I think it was a morning and. I discovered what actually happened years later, but what happened was she discovered him in bed with another woman. Um, and then came home in bits, which I remember vividly. Um, so a four-person household became three, me, my mom, 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. Um.

• 10:23Esther Perel?

  You're number one or number two?

• 10:25Speaker 04

  I'm number two. I'm the youngest brother yet. 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, which, which is great, but. They, I would have to 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.

• 10:55Esther Perel?

  Did you ask?

• 10:57Speaker 04

  So my sister was the was the vocal one. She kind of, she was sort of the campaigner on on both of our behalfs. She was one who would like to try and ask and try and understand them. 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 have it have it out. But, you know, that was twenty years ago. We we we've both come a long way since and have a great relationship with them now.

• 11:22Esther Perel?

  But you still haven't asked a question.

• 11:25Speaker 04

  I don't think I once asked my or have asked him ever what happened. No, literally not once.

• 11:31Esther Perel?

  So I think it's more than just what happened.

• 11:35Esther Perel?

  I think that there's a conversation with your dad about, you know, that this story that went on twenty years back, it still has a hold on my life. I feel lonely. I've 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 forty. I finally switched from thinking about all what was missing in the women I was meeting to realising that the story was inside of me.

• 12:18Speaker 04

  Yeah, yeah.

• 12:20Esther Perel?

  What what makes you laugh?

• 12:22Speaker 04

  Uh, I always laugh when I get nervous.

• 12:26Esther Perel?

  Okay, it's good.

• 12:27Speaker 04

  Yeah.

• 12:29Speaker 04

  I'm terrible with these feelings. I'm always laughing.

• 12:38Esther Perel?

  We have to take a brief break, so stay with us and let's see where this goes.

• 12:54Speaker 03

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• 14:50Esther Perel?

  My, 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 replaces your mother and which one replaces your dad? The withdrawal or the pursuit?

• 15:04Speaker 04

  As in, which one, i- is my mother this one, this or the other, is that what you mean?

• 15:09Esther Perel?

  Yeah, when you hold on.

• 15:11Speaker 04

  Hmm hmm.

• 15:11Esther Perel?

  And you become all needy, dependent, and please, please. When you cling, which, which story do you replay when you cling? And which story do you replay when you flee?

• 15:25Speaker 04

  Well, my feeling is that, um, when I'm clinging, that's definitely me replaying. Trying to get validation from my dad.

• 15:35Esther Perel?

  Hmm hmm.

• 15:36Speaker 04

  And it was my mum who pointed out to, to me that, um, until recently, anyway. The women that I, that I seem to be most drawn to were the stern ones. And I didn't see this, I did not see this common thing.

• 15:48Esther Perel?

  Hmm hmm.

• 15:49Speaker 04

  And it just made, and, and it just hit me hard, like it made total sense. She was right, so I feel that's, that's my dad. Um, I guess it's my mum, I don't know why it's harder to talk about my mum, I guess. My mum and I are very close, I haven't really thought about it like that, um, but I guess.

• 16:09Esther Perel?

  What is the feeling that makes you withdraw? You start to withdraw when?

• 16:14Speaker 04

  Hmm.

• 16:15Esther Perel?

  And you lose sexual interest when?

• 16:17Speaker 04

  Yeah, when I feel trapped.

• 16:19Esther Perel?

  Hmm hmm.

• 16:20Speaker 04

  When I feel contained.

• 16:21Esther Perel?

  And I feel trapped and contained when I feel? That's not a feeling, by the way, trapped and contained.

• 16:27Speaker 04

  Sure.

• 16:29Esther Perel?

  What is the feeling when you feel trapped and contained?

• 16:32Speaker 04

  Scared.

• 16:33Esther Perel?

  Hmm hmm.

• 16:33Speaker 04

  I feel, I feel scared.

• 16:35Esther Perel?

  And I'm scared of?

• 16:37Speaker 04

  Being seen for all my ridiculous ugliness. It's, it's, it's, it's what, it's, it's what it is. Being seen for this mess. Who hasn't got a effing clue what he's doing, um, who is?

• 16:53Speaker 04

  Who is sad quite a lot of the times, actually.

• 16:56Esther Perel?

  Mm hmm.

• 16:57Speaker 04

  Um, fuck, I mean, angry, constantly angry. I feel it, I feel, um, and I'm just worried about being seen as a bit of a head case. Being seen as a unsure of himself and uncertain and weak and all that.

• 17:17Esther Perel?

  Yeah, a human being.

• 17:19Speaker 04

  Basically, yeah.

• 17:21Esther Perel?

  Tell me something, our, what happened to your mom after your dad left?

• 17:28Speaker 04

  Okay, um, my mom was miserable, uh, for a long time. She was fucking angry and resentful.

• 17:41Speaker 04

  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 I 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 to help her.

• 18:09Speaker 04

  And she was just on the edge. She had breakdowns and I I.

• 18:15Esther Perel?

  And I felt trapped.

• 18:17Speaker 04

  I felt trapped, yeah.

• 18:18Esther Perel?

  Mm hmm.

• 18:19Speaker 04

  And I got angry at her. I was behaving like a brat. I I'm I was behaving like like a little shit. Who didn't wanna know about her misery and 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 wanna put distance between myself and that, you know, I don't wanna know because it.

• 18:40Speaker 04

  It's too close to the fucking pain, you know, I don't wanna know that shit and.

• 18:48Speaker 04

  I just didn't wanna know.

• 18:51Esther Perel?

  Tell me.

• 18:51Speaker 04

  And it make me angry.

• 18:52Esther Perel?

  Don't laugh when you wanna cry.

• 18:57Speaker 04

  I can't have that, man.

• 18:59Esther Perel?

  Cause you went through a lot. And you were a twelve 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.

• 19:16Esther Perel?

  And you were overwhelmed.

• 19:19Esther Perel?

  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.

• 19:37Esther Perel?

  And what better way to flee? And to reenact it also than to lose instant sexual interest.

• 19:48Speaker 04

  Yeah, it's the quickest way.

• 19:52Speaker 04

  Yeah.

• 19:53Esther 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

• 20:14Esther Perel?

  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.

• 20:38Speaker 04

  Yeah. Yeah, it's just so, just sounds so obvious when you say it this way.

• 20:45Esther Perel?

  This is new to you?

• 20:47Speaker 04

  Some of it is new to me. Um, it seems very obvious, but I've never heard it really put back to me that way before.

• 21:16Speaker 08

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• 23:13Esther Perel?

  What's the thing that touches you the most?

• 23:17Speaker 04

  You, you, you said responsibility and the sense of fleeing and that really, yeah, because the thing you said about how I just wanna make my own boundaries. I want my own life, actually. I, 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.

• 23:48Esther Perel?

  Yeah.

• 23:49Speaker 04

  Yeah.

• 23:50Esther Perel?

  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.

• 24:07Speaker 04

  Yeah. Mm hmm.

• 24:10Esther Perel?

  Where does that reach you?

• 24:14Speaker 04

  Ah, um, it's, um,

• 24:19Speaker 04

  I don't, I, I, I don't know how to answer the questions.

• 24:22Esther Perel?

  It's okay. It's okay.

• 24:23Speaker 04

  Yeah.

• 24:24Esther Perel?

  You can let it sit.

• 24:25Speaker 04

  But I'm kind of thinking, yeah, I'm just sort of like nodding to myself like, yeah, yeah. And no wonder I was so angry. And I still get angry at her. I, I honest to God, sometimes it's so, I feel so ashamed of it afterwards, but I can regret, as, as a thirty nine 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 of that because it's your mum. And, um.

• 24:55Esther Perel?

  And because you don't know of another way at this point to create some distance or some separateness.

• 25:05Esther Perel?

  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 you're, I think your romantic unconscious thinks that these women will be less needy. And you won't have to be so responsible for them.

• 25:48Esther Perel?

  Which may not always be the case, and that's not always the case, but that's how it appears at the beginning.

• 25:55Speaker 04

  No, no, that, that is so spot on. Um, I just came out of a relationship very recently. And again, surprise, surprise, four months, no, about. 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.

• 26:37Esther Perel?

  Yep.

• 26:38Speaker 04

  And this person saying, what the hell is wrong with you? Cause you're the one who was chasing me.

• 26:42Esther Perel?

  Yep.

• 26:43Speaker 04

  Mister, you know, like, what the hell? And I don't know what to say. I'm just caught, I'm just like, hands up. Yeah, I, I don't know. I don't know what just happened there.

• 26:51Esther Perel?

  Well, what just happened is that there's an overlap.

• 26:58Esther Perel?

  And it's easier to pursue someone who is holding back because then they don't overwhelm you.

• 27:06Esther Perel?

  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 gonna have conversations inside of you between the twelve year old and the adult.

• 27:33Esther Perel?

  Because some of this is fiction, meaning these women don't maybe need the kind of responsibility that you think they do. But you get this entire internal world activated at that moment. And it's about closing the gap between the twelve year old and the forty year old. When it comes to closeness.

• 27:59Speaker 04

  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, the reason I went to this person in the first place is pretty much for this thing. And I feel like this is it, like it just, this is it.

• 28:20Speaker 04

  I mean, I actually feel good about this, cause 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, for so long.

• 28:40Speaker 04

  And I just can't believe you're able to articulate it, like just, that's what it is.

• 28:45Esther Perel?

  We have articulated it.

• 28:47Speaker 04

  We have.

• 28:48Esther Perel?

  Not I, we have articulated it.

• 28:51Speaker 04

  Sure, sure.

• 28:51Esther Perel?

  Because if it, if it hits the spot, it's because you're right there already.

• 28:59Esther Perel?

  I could have said this to you ten years ago and it would land on their fears.

• 29:05Esther Perel?

  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.

• 29:20Esther Perel?

  You could even go back to the woman you just left.

• 29:25Esther Perel?

  And just say, I had a real reckoning and I understood something and I owe you an apology. If you're still interested.

• 29:34Speaker 04

  I can. I mean, we're still in touch off of all that.

• 29:37Esther Perel?

  Voila.

• 29:38Speaker 04

  Be very receptive to it, sure.

• 29:40Esther Perel?

  I feel she would be, yeah. So, um, that's the, that's... The more you bring that to her and you ground the experience with her in the present,

• 29:53Esther Perel?

  and then you say, "Look, I'm just beginning to disentangle this, but I know this had nothing to do with you.

• 30:01Esther Perel?

  Here is what I've understood in the meantime.

• 30:05Esther Perel?

  And if you choose that path, let me know. I'm very curious where that would go."

• 30:11Speaker 04

  If I reach out to her?

• 30:12Esther Perel?

  Yeah.

• 30:14Speaker 04

  Okay. I probably will do that. That for me would be a lot easier than the one about my dad, but I'll definitely...

• 30:20Esther Perel?

  Oh, your dad, I'm putting that one in the deck as well.

• 30:24Speaker 04

  Sure.

• 30:25Esther Perel?

  But I'm gonna leave you there.

• 30:27Speaker 04

  Sure. Esther, thank you so much.

• 30:29Esther Perel?

  You're welcome. Thank you so much.

• 30:30Speaker 04

  I'm so grateful.

• 30:31Esther Perel?

  My pleasure. Bye-bye.

• 30:32Speaker 04

  Take care.

• 30:37Speaker 00

  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 explore with Esther that could be answered in a forty or fifty-minute phone call, send her a voice message and Esther might just call you. Send your questions to [email protected]. 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, Destri Sibley, Sabrina Farhi, Kristin Muller, and Julianne At. Original music and additional production by Paul Schneider. And the executive

• 31:21Speaker 00

  producers of Where Should We Begin are Esther Perel and Jesse Baker. We'd also like to thank Courtney Hamilton, Mary Alice Miller, and Jack Saul.

• 31:37Speaker 03

  Support for the show comes from TikTok. There is a scientifically documented correlation between listening to podcasts and curiosity. So since you're here, you probably enjoy discovering new things. One great place to indulge your curiosity is TikTok. Whether it's how to forecast volcanic eruptions, strange phenomena that the James Webb Space Telescope picked up near the beginning of time, or a literal deep dive on the ocean's deepest reefs. TikTok has a wealth of fascinating videos just waiting to be discovered. Your next discovery is waiting on TikTok. Learn more at tiktok.com/discovermore.

• 32:21Speaker 06

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