‘How Much Work Should Dating Actually Be?’

Esther Perel is a psychotherapist, a best-selling author, and the host of the podcast Where Should We Begin? She’s also a leading expert on contemporary relationships. This column is adapted from the podcast — which is now part of the Vox Media Podcast Network — and you can listen and follow for free on Apple Podcasts or wherever you listen.

Dating is exhausting for this week’s caller. Despite her many attempts to find someone compatible, she has yet to find someone with whom she can envision a future. And although the caller, who is 33, is optimistic about finding someone, she is sick and tired of using the apps. “Unlike other aspects of my life, where I know that if I put in a certain amount of effort or focus, I’ll get better outcomes,” she says, the caller still ends up ghosted no matter how hard she tries.

Over the course of their conversation, Esther Perel encourages the caller to treat dating less like something she has to go and do. Instead, she should try to integrate it into her life as much as possible and open herself up to serendipity.

Caller: How much effort is a healthy amount to put into the pursuit of dating? I feel like I talk about it a lot, and it’s not in a “Woe is me” way. It’s in a “How do I solve this problem?” way. I’m genuinely curious about this. I know that after a certain point of thinking about the same topic, there are diminishing returns, and I’m just wondering where that line is.

There is a lot of discourse online, on Instagram and TikTok, where women are feeling this way. And the response is to decenter men and decenter dating, which I respect and can empathize with, but I don’t think that’s the right solution for me. In my opinion, it’s addressing the wrong problem. This isn’t about desperation of being someone’s girlfriend or wife; this is about building a true partnership, which is why I don’t want to give up on it or distract myself with something else.

I have amazing relationships with my friends and family, which I’m so grateful for. And I’m really happy with myself. I would just also like a partner who I can have a romantic relationship with and share other aspects of my life. I feel like I have pretty reasonable expectations of my future partner too — I don’t expect them to be my everything, but I’d like them to be a companion who I’m on the same page with, in terms of our values and aspirations for the future, and who also truly appreciates me. Very normal stuff. So I am optimistic, but I’m also exhausted.

Esther Perel: In a way, you have been more detailed about the optimism. The optimism is I know good relationships; I have good relationships. I don’t know if you’ve had romantic relationships as well?

Caller: I have, yeah.

Esther: Good ones?

Caller: Yes.

Esther: So you have good family ties, you are in a good relationship with yourself, and you know in general to put in the effort for things that you pursue. So there’s a lot of elements to your optimism. The “exhausted” part — I’m not clear on what your experience is. Tell me a little bit more about that.

Caller: I have been in two serious relationships, and I would say that they were generally good relationships, but they were not the right person for me. Besides that, I have tried dating and mostly just used the dating apps because I think that’s probably the easiest way. And I haven’t really found the kinds of people on that app that I feel I would be compatible with in the long term. I’ve also gone about it by asking friends and even family members if they could introduce me to somebody who they think I might get along with. Nobody’s introduced me to anybody that way. I’ve also tried to be really open-minded with the people that I already know: friends that I have, even former co-workers — people in my social circle. I haven’t really been able to find the right person in that way, either. So I’m just not really sure where to look. I guess that’s what I’m finding a little bit exhausting at this point.

Esther: I just want to add one other category, not that that is the answer but just because there is reaching to my social circle, reaching to my professional circle, going on the app — and then there is serendipity.

Caller: Absolutely. And that’s the optimistic part, I think.

Esther: You’re sitting in many planes. Because you travel.

Caller: I do.

Esther: You sit on planes, you sit in airports, you are in queues, you — the places where many times we used to meet when we didn’t have our head in our phones and we actually looked up and saw who was behind and in front of us. So I’m just curious: Are you at ease with happenstance, spontaneity, serendipity?

Caller: Absolutely. I would love that. I think that’s kind of the romantic part of me that wants to meet somebody on an airplane or in a queue, as you said. I just don’t know that I can rely on that. It feels like I need to be more intentional about it. What I’m finding challenging is how much effort do I put into this?

Esther: I think you said it very well in your question: “I want to have a robust life culturally, professionally, socially. I also want to meet someone for the next project of my life. I don’t want that to be the defining feature of my identity, of my sense of self-worth. But I also don’t want to personalize the story, as in I am feeling defeated, and so I’m going to deny the need. I’m going to make this no longer something that I pursue because I haven’t been successful at it. I want to remain open to it, but I don’t want my entire day and my entire structure of my life to be organized around I have a date. I need to go look at the app. I need to cancel everything else because somebody has just told me we have a date, then they cancel, then I have no plans, then I feel like I’ve put my whole dating life ahead of everything else and it takes priority, because you never know.” That’s the piece of effort that becomes not rewarding.

But I don’t know enough about how you’re doing it. To me, the effort is a level of openness. The effort is that people date not by putting their life on hold — as in I live my life to go date, and I create a distance between the two. And then when the date doesn’t work out, then I feel like there’s a void. The way that the effort becomes much more manageable is that you do your life, and if you happen to have a date, you invite the date into your life. But you may already be doing that.

Caller: I actually don’t find the dating part, as in, like, finding a date, challenging. I usually am able to go on a first date and have a really nice first date and even maybe a nice second date. But then it’s like there’s a difference in the effort that I’m willing to put in versus the person that I’m dating. That’s where the disconnect happens.

I met somebody who really seemed to be aligned with me in so many different ways. We had a great first date. We talked about some serious things because I wanted to be really intentional with where I was putting my time and my effort. I wanted to make sure that we were working toward a similar goal. It seemed that we were. Then we went on a second date and that was lovely, and we had a great time and again built up more of a serious type of a framework and understanding with each other. Then, because of our lifestyles — I was traveling; he was traveling — we tried to stay in touch. I was willing to put in that extra effort; we had spoken about how much time and effort we were willing to put in when we’re not physically together. And I just realized that I was putting in a lot more effort than he was. After a while, unfortunately, he just kind of ghosted me. That’s happened a few times. And I’m just like, Why is this happening?

Esther: What do you do when that happens?

Caller: In this case, he basically just stopped texting me. There was a regular cadence of communication. We had a time difference, and so I would wake up in the morning and have a text from him, and I would message him back and expect that he would get back to me at a time that was more appropriate for him. That was going on for, like, a few weeks. We had planned to see each other when we were in the same country again. And when we were planning the details of that next meetup, he just stopped replying to me. I wasn’t really sure why, because I couldn’t see anything in the conversation that would lead to him feeling a different way about me.

Esther: Did you ask him?

Caller: I did ask him. “Is everything okay? Did something change?” Never got a response.

Esther: In very simple terms, it’s beyond upsetting, because you begin to question yourself. You begin to question your sense of reality. Did I miss something? Was the whole thing an illusion? Is that what happens between people these days — we just toss each other away for whatever it’s worth? This is not going to change what you feel, but I can’t tell you how often I hear it. It’s between date four and five. Things seem to be going actually quite well. It’s not dragging. And the interesting thing is I hear it from everyone. I wish I had advice for this, but I don’t. I mean, not that thing specifically. I think it’s much more of a cultural thing, and a large societal phenomenon, than it is anything specific to do with you.

Questioning What’s missing in me? Or What have I done? Or What did I not say? Or What should I have said differently? This kind of microanalysis of every move is also off, because it makes us personalize social behaviors that have become acceptable. I would like to encourage you not to do that. It feels bad enough; you don’t have to feel bad about yourself.

Caller: Yeah, and I’m trying not to feel bad about myself. But then it’s hard to know what to do differently the next time.

Esther: Because you know what? If you feel bad about yourself, it gives you a weird sense of agency — that there’s actually something that you can do differently. I’m not sure that there is much that you necessarily want to do differently in dating online. But what you may want to do differently is create new situations that increase the possibility of meeting people. I’ll tell you one that I like a lot, and I’ve said this in other places, but those who have followed it, I’ve liked what they’ve told me.

It’s about bringing people together. You with two or three other friends: Each of you bring three, four people that you don’t know, and you do it every two weeks, and you begin to increase the number of people that become a part of your social circle — some of them just for the night. But the next time, you ask those people to bring two or three people with them. You do a potluck. You don’t have to cook for 30 people. But the idea is to proliferate new connections from within, but to the outer circle. It’s curated, so there is a choice element to it, and there is enough unknown that you can be surprised.

Caller: I like that. That’s a good idea. I’ll try it.

Esther: What are things you enjoy doing in your leisure time?

Caller: Quite a few things. I am really into dancing. I go to dance class a few times a week.

Esther: What kind?

Caller: Belly dancing, actually. So I really enjoy that. I I love going to the beach and doing anything kind of water sports–related: snorkeling, swimming, surfing, paddleboarding — anything that gets me out in the water. I love going to art galleries and museums. Anything creative.

Esther: The reason I ask is because I’m looking for opportunities, right? There’s two sets of questions in my mind. One is the setting; the other one is the conversation.

Where does one meet people? When I think about dating these days, I think about how to integrate it into your life so that you don’t go looking for the dates — you have situations that may be propitious for dating. Belly dancing is probably not the dance where you may meet partners, unless they come to watch you, but that may follow. But there may be other kinds of partner dancing that you may enjoy too.

You like art; you like going to galleries. Sometimes it’s about going to a talk in a gallery, but the problem is people are not talking to the neighbor standing next to them. However, there is a way to bring 20, 30 people to a gallery, even with somebody or to someone’s home, and to create a salon. You create situations where people come together. Because we want curation. The app is meant to curate, but that doesn’t mean we have to relinquish all our opportunities for curation.

But I have another question: Tell me more about the conversation when you said, “We were going more serious. We were trying to align our values.” What exactly was serious? What are the values? What’s the deeper layer?

Caller: We spoke about our longer-term goals for ourselves and the lifestyles that we imagine for ourselves and how a partner would fit into that. And our hopes for family and the way that we would live and prioritize different things in our lives.

So, for me, being able to travel a lot is important. That’s something that I let people know up front. This is a really big part of my identity and a goal that I have for the future. Is that something that’s in alignment with you? I don’t personally really know if I want to have biological children. It’s not a main goal for me. So having a discussion with the other person to see “Is that really important for you? What kind of a parent would you like to be?” Lots of different, deeper questions that are not just, like, “I find you attractive. Do you want to go on a date with me?”

Esther: Right. What model of relationship did you grow up with? How did your parents meet?

Caller: My parents actually met through my aunt. My mom’s sister was friends with my dad, and she made the introduction. Interestingly enough, they were both considered, for the time — as in they were both in their 30s and sort of resigned to the fact that they didn’t think that they were going to find a partner. Then they met each other, and they both had very strong opinions about things. Apparently, their first conversation was an argument, and they both really enjoyed being able to have a very spirited conversation, and they were like, I think I think this person could be the one.

Esther: Did they live a traditional relationship? Did they become westernized? What models of relationship did they embrace?

Caller: So I would say not traditional by any means but not necessarily western, either. Both my parents have had pretty international upbringings as well. My grandfather was a diplomat. My other grandfather was in politics. So they both have lived in a lot of different places and have a very multifaceted identity of their own. They raised me and my sister in a pretty nontraditional way as well. They both are feminists. They instilled a lot of messages of empowerment and independence to both me and my sister. That’s the foundation that I’m coming from. So, also, I think meeting somebody who has very traditional gender ideas is off-putting for me.

Esther: How long do you stay in communication before you meet in person? I mean, how quickly do you figure all of this out and how?

Caller: So I typically like to speak to somebody on the phone before I meet them in person because I feel like you can have a great conversation over text, but you may not actually be able to carry a conversation. Usually within a few days. Again, I don’t like to waste my time or their time. So a phone conversation. And then if that goes well, then I’d like to meet them sooner rather than later.

Esther: Was that always your premise, or did that augment with years?

Caller: I was in two very serious relationships. One was for five years, and the other one was for two years. So pretty much my entire 20s, I was in relationships. I didn’t really have a lot of dating experience outside of that until my early 30s. And by that time, I feel like people are a lot more pragmatic and don’t want to waste each other’s time.

Esther: Do you think that that approach is conducive or makes you so focused on the prize that you end up not seeing what’s in front of you?

Caller: My intention when I’m meeting somebody is not necessarily to see whether they’re the one but to see if we have some kind of connection or spark and maybe they could be a friend. I think I go into the first meeting quite open-minded, but then when we meet, and if we do seem to be connecting, I want to see more about the long-term expectations, if we are compatible in that way, and proceed from there.

Esther: I ask you because sometimes we are so focused and clear and instrumental it changes what we are looking at. It changes our perception, and it changes what we value and what we pick up. Interestingly, when you meet someone casually, spontaneously, unplanned — if I happen to just meet someone at the bakery, I’m not at all thinking about not wasting someone’s time. I’m enjoying the surprise, and I’m wondering, To what extent does this change our experience?

There’s something that kind of closes off the story sometimes. I’m not saying this is something you do, nor that it’s something you must change, but I do have a sense that if I meet you and we start talking and I enjoy it, and then we extend it from three minutes to ten and to 20, and then we say, “Let’s continue this,” or “Where are you off to? I was just going about here — you want to join me?” None of us are thinking about wasting time. Are you my type? Do you at least answer the basic questions? Do I answer your basic questions? It’s more fun. It’s more open-ended. I don’t know how one creates that in the virtual world: that sense of anticipation.

Caller: In my experiences so far, I actually really enjoy the pure curiosity of, like, Who is this person that I’m going to meet? What are they like? I’ve met many characters in my day, and I’m happy to keep them around as friends. But I think what has been the challenge for me so far is that I’m not usually the one putting in a ton of effort at the beginning. It’s usually somebody else who seems to be taking more of the initiative with me up until date four, like you said.

Esther: Do you bring it up with them?

Caller: I have, actually. I’ve kind of said that there’s a pattern, and they’re like, “That’s so weird. I don’t know why that happened.” Like, completely making it seem like it could never be them — they could never do that. Then lo and behold.

Esther: But the person who you just talked about — he did that too?

Caller: Absolutely. We talked about all these things that we’ve disliked in our dating experiences before. One of the things that we had in common was when there seems to be mutual interest and then somebody just ghosts. And he did the same thing.

It’s not an isolated incident. This has happened to me, like, three times. It was the last one that made me write into your show and be like, Let me get a professional’s opinion on this.

Esther: I haven’t said anything that you don’t know yet, though. I wish I had an original thought about it that you may not have heard yet, but I have a feeling that we’re hearing the same thing over and over.

The only thing I may have said: When you wrote to him and you knew he had suddenly gone blackout. The first message might be “Is everything okay?” And the second one is “We said we wouldn’t do this. Let’s just give each other the courtesy. It’s totally fine; let’s not dump each other like that.” I don’t know if you would get an answer, but at least you have closed the loop.

Caller: I think that is the struggle. I think the way you phrased it is really good. But the reason why I haven’t sent a follow-up after I haven’t gotten the response is because it does feel a little bit embarrassing. It feels like — I don’t know what the right word would be …

Esther: Lke you’re crawling.

Caller: Yeah. That’s why I haven’t. But then it also means that there’s no accountability for that behavior.

Esther: That’s right. So you don’t want to crawl, you don’t want to beg, and you don’t want to blame because then they shut up. And so it’s this very fine-tuned — but because you discussed how: It’s happened to us. We discussed the things that we don’t like in the system. We discussed the things we appreciate in the system. You have a reference, and the reference is “It’s too bad, because we really talked about it and we both seem to dislike similar behavior. Why fall into this right now? I get the message, but I would appreciate you conveying it to me in a way that is civil, that is kind. That’s it. I think we can do better. We may never see each other again, but we can do better. This is a call to humanity; this is not a call to me and you. This is a call of the society we want to live in. Why create a situation that’s going to make us go to therapy to discuss this?”

Caller: Exactly.

Esther: “Then it becomes a problem to bring to my therapist rather than a societal issue in which something is off and we should not let this happen. We are screaming for a lot of different ideals. Let’s scream for the ideal of civility and kindness and maturity. It’s not a good feeling to walk around knowing that you treat people poorly. You will learn to say ‘No, not interested. Moving on.’”

Caller: I feel like, right now, I am burned-out with the apps. I don’t want to do them anymore. Is there also a part of me that needs to be okay with the possibility of never finding somebody?

Esther: It goes from finding to never finding. No. Life can have twists and turns in every direction. One of the special things about life today is that people meet partners at various stages of their lives in all kinds of unforeseen circumstances. The story is much less linear than it used to be: You met somebody, you married them, then you had sex with them, then you had babies with them, etc., etc. This is a bit of an older story, but it still is the story in the majority of the world.

We’re in a different reality. You can start at 25, and you can start at 55, and marry for the first time and have a family in ways that you never had imagined. So I don’t think of it as yeah/nay, hopeful/hopeless. I don’t. Because you go back and forth between Where am I at? How much do I put this as the focus? That’s why I keep saying it’s an important piece and you remain open to it, but you don’t leave your life in order to go date.

Caller: Totally.

Esther: You integrate dating into your life. That is clear because that’s the most important piece of sustainability. Otherwise, what you’re describing, I get burned-out. I get off for a few months, then I feel like I should start again. Then I go back, put the profile back in, review the profile. I’m not surprised you start with the sentence “I’m optimistic but also exhausted.” Because it’s exhausting. And not just to you. It’s exhausting. And at the same time, it’s the most extraordinary curation that has ever happened. It’s a lot of different things.

All I can say is don’t just stay focused on that. Create other touch points because you actually don’t know where that person will be and where that meeting will take place. With this person, I can imagine a story of life — a life story, not just a love story.