Still Single at 40

25 Aug 2025 · 30 min · 9 chapters

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In short

A caller (“pushing 40”) can’t sustain romantic relationships past 4–5 months, alternating between anxious clinging/pursuit and passive withdrawal, including losing sexual interest; Esther explores attachment fears and links the pattern to early caregiver dynamics.

Guest background

The caller is a 39–40-year-old man with long friendships but recurring romantic breakups around the same time. He reports being charming at first, then becoming needy/latchy or avoidant; he feels responsible for partners’ emotions and fears being “seen” as a “head case.” He laughs when nervous.

Key claims

The pattern is driven by his internal “12-year-old vs 40-year-old” conflict: closeness triggers fear of caretaking responsibility (fleeing) or validation-seeking (clinging). Romantic partners mirror early caregivers because stakes feel similar.

Notable examples

His parents divorced when he was 12–13 after his father’s affair; his mother became angry/miserable and he felt trapped trying to manage her emotions. In a recent relationship, he chased someone who was initially offish, then withdrew once she became warm and close. Esther suggests he “disentangle” and even apologize to an ex with what he learned.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Exploring Relationship Patterns

0:01 to 1:50

A caller shares their experiences with brief romantic relationships and feelings of anxiety.

“And to this day, I've never had a relationship that's gone beyond four or five months.”

Delving into Emotional Barriers

2:25 to 12:20

Esther and the caller discuss the struggles of being authentic in romantic relationships and the impact of past experiences.

“These statements have not been evaluated by the Food and Drug Administration.”

Parent-Child Dynamics

13:35 to 14:00

Discussion about the caller's family background and how those experiences shape their romantic relationships.

“and the new original series, The Five Star Weekend.”

Introduction to the Session

14:00 to 14:21

Exploration of personal struggles and relationships begins.

“Her strained marriage, her complicated relationship with her daughter and her growing pursuit of validation from her fans.”

Understanding Withdrawal and Clinging

14:21 to 20:36

Discussion on emotional withdrawal and the desire for validation from parents.

“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 replaced your dad?”

Sponsor: Ollie and 7-Eleven

20:36 to 21:48

Promotional segment for health supplements and 7-Eleven offerings.

“We'll be back with a session right after this.”

The Cycle of Responsibility and Fleeing

21:48 to 27:00

Analyzing the cycle of emotional responsibility and the instinct to flee from relationships.

“Participating stores only while supplies last.”

Realizations and Apologies

27:00 to 28:00

A breakthrough moment as the speaker connects past experiences with current relationships.

Reflections on Past Relationships

28:00 to 29:40

Explore the importance of accountability and growth in relationships.

“I mean, we're still in touch after all that.”
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Transcript

Automatic transcript. May contain errors.

0:00What 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.

0:12Hi 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 um three four months into the relationship whatever i 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 just ends because I just can't communicate what it 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 thank you

1:50We'll see you next time. dot com slash prime to find millions of items delivered fast same day delivery it's on prime available in select areas terms apply hey friends olivia from ollie between new routines and the ultimate group project known as parenting you need science-backed solutions that work with your life that's where ollie comes in start your mornings off right with multis made to support nutrition and immune health choose from our lineup of gut supporting probiotics and we've got occasional sleep support to help the whole fam chase their big dreams. Head back to class with the number one gummy supplement brand.

2:23Stuck up on Oli.com today. These statements have not been evaluated by the Food and Drug Administration. This product is not intended to diagnose, treat, cure, or prevent any disease.

2:42Hi. Hello, hello. This is Esther and... Hello. I read and listened to your message, but ask me your question again. Well, I guess the question is, as I'm pushing forward 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? And you mean all relationships? You mean romantic relationships, friendships as well? I'm talking strictly romantic relationships, yeah. You have long-standing friendships. Yeah, definitely.

3:32Great friendships. I have friends who I've been with for, who have been best friends for well over two decades. 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? I mean, I do ask myself. Absolutely. And I guess the simplest 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.

4:21But 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. I was putting on constantly. Because I was protecting myself against what? 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. and what how does it manifest 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 um 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 you know 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 or the flip side um 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 um oh and of course i guess the main thing is I lose interest in sex.

5:56I 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. 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.

6:36And 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 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.

7:29Exactly. Right? Which is what you probably thought for the first 10 years. Yeah. Yeah. 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?

8:17Because 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 with our friends. 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 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 okay um so my parents got divorced when i was uh 12 13 um it was a terrible divorce just an absolute park crash and in what in what sense 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 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 the morning and I 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 um you're number one or number two 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 stayed 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 when 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 on both of our behalves she was one who would like to try and ask and try and understand and my role was passive I would just sit there a 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 that we we both come a long way since and have a great relationship with them now but you still haven't asked a question I don't think I once asked him or have asked him ever what happens no literally not once so I think it's more than just what happened.

11:15I 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. 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 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. Yeah. Yeah. What makes you laugh? I always laugh when I get nervous.

12:06Okay, that's good. Yeah. I'm terrible with these feelings. I'm always laughing.

12:18We have to take a brief break. So stay with us. And let's see where this goes.

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13:30Valid through 825-26. Participating stores only while supplies last. Visit store for full terms. Support for the show comes from Peacock and the new original series, The Five Star Weekend. Jennifer Garner stars as Holly Shaw, a famed cook known for her delicious recipes and impeccable taste. After braving a devastating loss, she decides to invite her best friends to a getaway on Nantucket. As boundaries are pushed, friendships are tested and secrets are exposed, cracks begin to emerge in her picture-perfect life. Her strained marriage, her complicated relationship with her daughter and her growing pursuit of validation from her fans.

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14:28My 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 replaced your dad? The withdrawal or the pursuit? As in, which one? Is my mother this or the other? Is that what you mean? 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? 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 mom who pointed out to me that until recently anyway, The women that I seem to be most drawn to were the stern ones.

15:23And I didn't see this. I did not see this common thing. And it just hit me hard. It made total sense. She was right. So I feel that's my dad. I guess as 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. But I guess... What is the feeling that makes you withdraw? You start to withdraw when? And you lose sexual interest when? Yeah, when I feel trapped, when I feel contained. And I feel trapped and contained when I feel... That's not a feeling, by the way, trapped and contained. Okay, sure. What is the feeling when you feel trapped and contained?

16:10Scared. I feel scared. And I'm scared of? being seen for all my ridiculous ugliness is is is what it is is what it is being seen for this mess who hasn't got a effing clue what he's doing um who is who is sad quite a lot of the times actually 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 uh unsure of himself and uncertain and weak and all that yeah a human being basically yeah tell me something our what happened to your mom after your dad left? Okay. My mom was miserable for a long time. She was fucking angry and resentful.

17:18And 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 to help her and she was just on the edge she had breakdowns and I And I felt trapped. 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.

18:04And I hated that sense. 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. I don't want to know because it's too close to the fucking pain. I don't want to know that shit.

18:27I just didn't want to know. Tell me. And it made me angry. Don't laugh when you want to cry.

18:35I can't help it. 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 than to lose instant sexual interest yeah it's the quickest way yeah 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.

19:44And 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 the boundary so that he can deal with his own life. And he pretends he doesn't care, but in fact, he cares so much. Yeah. Yeah. It's just so, just sounds so obvious when you say it this way. This is new to you? 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.

20:36We'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 Astaire's Office Hours on Apple Podcasts.

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22:20What's the thing that touches you the most? you you you said responsibility and the 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 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 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 yeah Yeah.

23:17Where does that reach you?

23:26It's, I don't know how to ask the question, to be honest. It's okay. It's okay. Yeah. You can let it sit. 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 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 of that because it's your mum and and because you don't know of another way at this point to create some distance or some separateness without having to have a yelling match.

24:18And 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. No, no, 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 have 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 yeah and this person's saying what the hell is wrong with you because you're the one who was chasing me yeah 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 don't know I don't know what just happened there well what just happened is that there's an overlap.

26:04And 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 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 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 in 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 we have articulated it we have not I we have articulated it sure sure because if it if it hits the spot it's 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

28:27you 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. I can. I mean, we're still in touch after all that. And she'd be very receptive to it, for sure. I feel she would be, yeah. So 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.

29:18If 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 work on that one. Oh, your dad, I'm putting that one in the deck as well. But I'm going to leave you there. Sure. Esther, thank you so much. You're welcome. Thank you so much. My pleasure. Bye-bye. Take care.

29:44This 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 40 or 50 minute phone call, send her a voice message and Esther might just call you. Send your questions to producer at estherperel.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 Farhi, Kristen Muller, and Julia Natt.

30:23Original music and additional production by Paul Schneider And the executive 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

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From the publisher

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 producer@estherperel.com.

Want to learn more? Receive monthly insights, musings, and recommendations to improve your relational intelligence via email from Esther: https://www.estherperel.com/newsletter
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