From 23 To 53: A Conversation About Manhood

SOLO 182 | Manhood


Peter (age 53) has a conversation with Daniel (age 23) about sex, dating, and what it means to be a man.

From 23 To 53: A Conversation About Manhood

Welcome Daniel. The premise of this episode is a conversation between two bachelors 30 years apart in age. I’m the older one. Let’s get to know you a little bit. Who’s Daniel?

My name is Daniel. I’m a graduate student in California. I study Math and Engineering. I’ve grown up in California my whole life.

Where’s your family from?

My parents emigrated here from China, but I was born here in the States. I guess I’m the first generation in my family, at least, to be born in the US.

How did we find each other?

I started reading a couple of the Solo episodes. I forgot exactly how I found it, but I think I was just scrolling. I’d never heard of a show like this before covering this kind of topic, and I was interested. I thought that the guests that you had invited talked about the different ways that they live their lives. I like your saying to live a remarkable life. I thought that was cool. I decided to reach out to you through your website contact email because I was, at the time, and I guess still now, trying to get into the self-improvement area.

When you see you were scrolling, were you scrolling with a purpose?

I looked up a list of self-improvement podcasts or just random things on Reddit or forums, and this might have been one of them. I forgot exactly how.

It was a while ago. I remember that. We were still 30 years apart. You send me this email, and correct me if I’m wrong. I emailed back and I said, “Here’s my phone number. Give me a call or send me a text.”

Yes, you did.

It was because you had some questions and we ended up talking. We are having a conversation about manhood. That’s what this came down to, about masculinity and manhood. I had a half inedible in me and so I was letting it fly. It was a spirited and fun conversation. I then got the idea of, “Why don’t we have this conversation on the show?”

I asked you to prepare some questions. You’re going to be asking me some questions, and before I do that, I want to begin with the warning label of sorts. This is not for you as much as it is for any reader. The first one is I’m not as prepared as I would normally be for this kind of thing only because I’ve been so distracted by the writing process. I’m working on a book.

This could be a little bit more off the cuff, and that’s fine. This is conversational. I may miss some things and I’ll probably regret it more than anyone else. The second thing is that this conversation, I suspect, is going to be largely heteronormative. I don’t know your orientation, but from our previous conversation, my suspicion is that this is going to be to straight men talking.

Yes. I’m straight.

There are going to be things that are going to be missed as a result of our limited experience as straight men. The last thing I want to say is that I’m going to speak frankly and I’m speaking unapologetically. That’s important because of how unpopular men are at the moment. People might be surprised if I point out the good that men do in this world and how essential it is for us to celebrate men and women when they collaborate and when they bring their own unique strengths to society. With that said, I have very little tolerance for the misogynistic perspectives that you get from these red-pill manosphere types. I don’t know how familiar you are with that or whether you’re scrolling revealed a bit of that world.

I know that there are pockets of the internet that are quietly misogynistic in general. It’s terrible.

Any world where men hate women or where women hate men is an unacceptable world to me. I don’t have much tolerance for that kind of intolerance. We’ll see how it all goes. Are you ready to jump in?


Hit me with your first question.

One thing that I would say to people my age from asking my friends is that there’s the standard that by a certain age, you should have achieved a certain number of things. Pertinent to this whole show, you should have a relationship by his age, you should have dated a certain number of people by a certain age, or you should move in by a certain age. If people don’t see that you’re on track to hit these milestones, they might ask, “What’s going on?”

“What’s wrong with you?”

Yes, but without saying it, or maybe they would say it. Personally, I felt like, “Is there something wrong?” I don’t know. Also, I’ve wondered. I don’t know how much women think about this, but if women ask as a guy if you haven’t been with a certain number of women before, do they see that as a red flag? “What’s wrong with this guy? He’s a certain age and has never been in a relationship and stuff like that.” I know that a lot of other guys my age are insecure about that as well. I want to ask, “What do you think was most helpful to you in getting rid of this timeline pressure?”

Daniel, I have to give you credit for even considering this question because when I was your age, I was young, dumb, struggling, and not even contemplating the meta element of all of this. I also didn’t have Spotify to scroll through. I had to try to answer these questions. Let me start with myself for a moment to set perspective. That is I was a late bloomer.

I was late to relationships. I was late to sex. I would have failed any of those questions about, “You should have done this and that by now,” and so on. It is funny because, simultaneously, you’re supposed to have a certain amount of experience by a certain age, but you’re not supposed to have too much experience.

That’s true too.

People talk about body counts. I find it to be a distasteful way to think about intimate relationships. “What’s your body count? How many people have you slept with?” If the numbers are too low, that’s bad, or if the numbers are too high, that’s bad. Especially if you’re a woman and the number is too high, that can be seen especially badly. It’s interesting to have people ask you these questions and to have commentary about something that, in some ways, is quite personal and not much their business necessarily. I recognize when it comes up on a date that it is a way to ask a question that you don’t want to ask.

I feel like when I’m asked that question, sometimes it feels like you’re being asked, “You’re a desirable guy because if you are desirable, then people must have wanted to be with you before.”

How do you judge whether something’s valuable? It’s whether other people want that thing. Auctions are like that. “This other person’s bidding for this. I should bid for it too.” It’s psychological principles around scarcity, for example. The people value things that are scarcer. Someone who has a busy dating life is scarcer than someone who’s, “I could meet you tomorrow. I can meet you the next day. Whenever you’re available, I’ll go out with you. Yes, please,” and that kind of thing.

I’m going to use another term that comes up in academia and has found its way into TikTok and beyond, which is trying to assess mate value. Is someone high value or are they low value? They’re using your dating and sexual history in a sense to figure that out. They’re trying to figure that out because they’re trying to figure out whether you’re worth spending time with.

I don’t blame women for that in a sense, “Do I need to teach this guy the basics of what he needs to know in order to be a good boyfriend or in order to be a good lover?” There’s a little bit of that kind of thing, but I think it goes beyond that sussing out “mate value.” This is a much bigger topic, and I’m about to get very nerdy here for a moment. Also, one last thing. This is a digression. I was a total late bloomer and I desperately wanted to have sex. I desperately wanted to have a girlfriend.

I wanted to fall in love. I wanted to experience those things. I did feel behind in a sense because my friends were doing it. It’s exciting. It’s appealing, and it’s what you ought to be doing. You’re in college. You’re in your twenties. You’re supposed to be young and this is an exciting time. It’s also, in some ways, a little bit of a low-cost time to be doing that societally because you don’t have to be making major decisions. You don’t have to find the one when you’re 23 years old.

I’m glad in hindsight that I was bad at it because A) It makes me more appreciative of it now. I don’t take it for granted, and B) It forced me to work on myself. It led me to become better at life and more interesting. I threw myself into my academics and my athletics. When I had a chance, I started to travel. I have to be unencumbered and invest in myself in a way that ends up paying off in the long run.

Thirty years later, here I am. I’m still fit. I have a successful career. I’m a much more interesting man than I was when I was 23. I was fun. I was a nice guy. I like to say my spine is still the same. I’m still the same person deep inside and deep down. I just have a lot more to offer as a result of investing in myself. If I had been good with girls early, I’m not sure I’d be so successful now. I wonder if I would have coasted a little bit more.

Honestly, that’s motivating too. I feel like I’m a bit behind the curve as well. I know someone, and she’s a girl so it is not exactly comparable. From basically age eighteen until now, she said that she’s only spent three months outside of the relationship. She’s always been in a relationship. I’m like, “Some people are living a completely opposite relationship ratio to me.” I wondered, “Are more people in one for a longer duration of their time?” I study Math stuff. I’m like, “What is this ratio supposed to be?”

The answer is it depends on the person. There is some data about this. That is young men tend to be single and young women tend to not be single. Why is that? Some of it has to do with how appealing young women tend to be when it comes to looks and their willingness to date men who are older. Also, the willingness of older men to date younger women. This could be a difference in age of two years or it could be a difference in age of ten years.

As a result, young women have a lot more opportunities to be in a relationship if they want to be. Young men, of which I was once one, aren’t as appealing in part because we haven’t accomplished very much in our lives, and that tends to be something that women tend to want. The same is not true. Young men don’t tend to date older women.

It happens on occasion and so on. There are exceptions and whatnot. You’re living in a world right now where a lot of young women have boyfriends and are dating. They have lots of opportunities, and there are a lot of young men who are trying and failing. At some point, the good ones, the ones who don’t turn into misogynists, the ones who continue to work on themselves, will eventually start to have a little bit more success if they want.

Heteronormatively, there are problems around genders like women or at least, women of my age. There are a lot of creeps out there and terrible people trying to take advantage of them. There are a lot of unsolicited things like when they’re dating online. I guess men my age have another problem, which is more like, “How do I learn that I’m not like a creepy crazy person?” I’m like, “I don’t want to be too forward because I don’t want you to think I’m one of those creeps.”

Creep is worse than desperate, but desperate is still unappealing.

I’m my own person, and this is not a need to survive or anything like that. Generally, you shouldn’t be desperate. Also, you don’t want to come off like that either.

The best way to not be desperate is to not be desperate versus being desperate and hiding your desperation. It’s hard because you have these sexual drives. A young man often has very high testosterone. Once these things are having difficulty getting it, figuring it out, and understanding it, they lack experience and appeal. What you’ve been saying very kindly is they’re also getting a lot of pressure that you ought to be doing this. This is what you are supposed to be doing. This is part of being young and you’re getting on a track to eventually ride the escalator and figure that stuff out. Biological drives aside, that come from society.

Pre-digression and getting back to that, this notion of time is made up. Time is a fiction. It is something that we agree on. This invention of seconds, minutes, hours, days, months, years, and so on. We agree on it and we use it. It’s a tool that’s very useful in the same way. Money is something that we made up and a tool, and it’s useful and so on.

We know it’s made up because not every culture shares the same perceptions of time. There are indigenous cultures that have different calendars and think of the past in front of you, the future behind you, and so on. We know that any anthropologist who looks at time understands this. However, what we have done not just with time as a psychological concept, but time as a sociological concept is that we now have these benchmarks associated with time that we’re supposed to have done certain things by certain times that are often culturally determined. Have you ever seen the movie The 40-Year-Old Virgin?

No, but I’ve heard endlessly about this movie.

It’s a rom-com. It’s a quite lovely touching movie. The premise is about a guy who’s living a happy life and has not had sex yet. This becomes a task of his friends to help him devirginize. That’s the whole premise of the thing. If you think about it, that’s non-standard. That’s not right. We need to come in and fix this guy and his problem.

A lot have not seen the movie. I know the general premise, and it was portrayed to be very childish despite the fact that he’s 40 years old. It’s like, “You’re not a man until you’ve done this.” I’m not a sociologist so I don’t know why, but I’m saying that a lot of the pressure that at least my friends and I, or in general men our age face is because, in your early twenties, there are so many directions you can go into what makes you a man.

What is it that makes someone a man? What makes a boy a man? What makes a girl a woman? What makes someone an adult is often the question, and these relationship benchmarks are one way that people do it. However, we have a whole bunch of other ones too. When are you supposed to go to college? When are you supposed to move out of the house? At what age are you not supposed to have roommates anymore?

Traditionally, you’re supposed to be broke and young in your twenties. By the time you’re 30, you’re supposed to be partnered up. By 40 years, you are supposed to have a house.

There are all these things, and they’re built around these arbitrary norms. Now, in this age, even though people don’t partner up as often as they used to, they don’t have kids as often as they used to and they don’t marry as young as they used to. Back in the day, oftentimes, you were supposed to lose your virginity on your wedding night. There was not supposed to be any premarital sex. The loss of virginity and marriage go hand-in-hand, and that was the benchmark that you are now an adult. That’s a pretty terrible benchmark to be perfectly honest. You can be quite childlike and be married, especially if you let your spouse parent you.

I’ve read suboptimal arrangements where one person is doing all the work of raising the entire family and the other person’s maybe not doing anything.

Either, they’re doing this classic breadwinner homemaker role where the husband looks like a man because he goes to work every day and brings home a paycheck, but his wife is doing the emotional caregiving. She is taking care of the household, and if she left him, he would struggle. He wouldn’t be able to feed himself. He wouldn’t be able to clothe himself. He would have no resources to be able to soothe himself.

If you’re going to be a man, you should at least be able to feed, clothe, and take care of yourself.

One of the best episodes that tackles this question more deeply is called Waiting. It’s with Kinneret Lahad who’s a sociologist at Tel Aviv University and a guest co-host, Iris Schneider. We talked about this notion of waiting. We did it mostly in the context of women waiting for a family and the notion of a biological clock, but the insights from it are apt for what we’re talking about now. That is the problem with these benchmarks, and the benchmark might be losing your virginity, moving out of your parent’s house, having a girlfriend, owning a home, or, in the case of what Kinneret was talking about, having a family or a child, is that you put yourself in a powerless situation when you’re waiting.

That is, you have some goal and your life is worse off until that goal is satisfied. You are less than. You’re living in this liminal space. The problem with this is that people internalize this and they feel like there’s something wrong with them because they haven’t been able to achieve this thing, and it’s enforced by society. It’s enforced, I often think, in a well-meaning way. These are people who often care about you. They want you to succeed or, at the very least, they’re neutral about it. They’re trying to suss out, “Will this guy be a good boyfriend? I don’t know. I don’t want to have to teach him where the clitoris is,” and these kinds of things.

However, the problem is that these benchmarks are arbitrary. They certainly don’t take into account a person’s individual needs and desires, what they want from their life, what they are ready for, and what their privileges or lack thereof lead them to be more or less successful in this endeavor that they may be choosing an alternative path also.

That often helps a lot because you start having this, “Daniel, it’s time to start acting your age,” is one of those things that people end up saying. That’s unfortunate because I’d like to celebrate childhood in a lot of ways. This was a playful time. It’s a time of curiosity. Getting people to “grow up” and leave behind childish ways, it’s unfortunate if you have to leave behind your curiosity, your playfulness, your excitement about life, and so on in order to buy this house that’s too big and then work tirelessly to pay for it. Also, spend your weekends cutting the lawn, cleaning the gutters, painting it, and doing all these things rather than having adventures.

Now, there are so many different paths that people can take. I know there’s something called digital nomads where people move across different countries and work completely remotely so they don’t have to ever settle down if they want to. Let’s say they want to settle down, people can have their own startup, and that’s seen as prestigious, at least, in the Bay Area. Whereas before, prestigious jobs were stable like a doctor, which they still are. I’m a bit luckier that now, it’s more normalized, at least, in California, to be a little bit offbeat.

I’m excited for your generation. I’m a tiny bit envious because I lived in a world where, at least, you get mixed messages. I was getting a singular message, and my message was, “Peter, if you’re not careful, you’re going to turn into a 40-year-old virgin.” I managed to avoid that, but I’m okay with people being late bloomers. I’m okay with people having challenges around these topics when they’re young as long as they react to them in a growth-oriented fashion.

There’s a term for what I was when I was in my early twenties. I was an incel, an involuntary celibate. Ironically, the term was invented by a woman, but it’s overwhelmingly attributed to young men. I did a survey where I asked people their attitudes towards various words associated with relationships and non-relationships. On 100-point, incel was the lowest. It got a 9 out of 100. It was a negative rating.

From my understanding of that word, that’s basically a guy who lives in his mom’s basement. He can’t take care of himself and thinks that the world owes him something or that people owe him sex or whatnot. Probably, I’d rate it a negative number.

There have been some acts of violence by self-identified incels. The unfortunate thing is not every man would like to have a girlfriend, fail, live in his mom’s basement, hate women, and so on. The men who choose to try to improve themselves are the ones who, in the long run, are going to be okay. I had someone ask me in an episode, “What would you tell an 18-year-old or 25-year-old Pete?” I said, “I would tell him it’s going to be okay. Just keep doing what you’re doing. Keep your chin up. Keep growing, and it’s going to be okay. We live long lives.”

In some ways, the nerds win. They get educated. They get good work. They’re thoughtful. They’re introspective. If they can remain optimistic, it can often be good. I want to ask you a question because navigating the questions that prompted you to ask me this one is not easy to do. The tendency is to be defensive because they feel a little bit accusatory.

How do you find yourself when you get a question about your dating history? You’re not there yet, but there’s a question you’re going to start getting in your 30s. It’s this. “Daniel, how long was your longest relationship?” Now, you’re too young for that to be a consideration, but that would be a question that would put me on the defensive because my answer to that question, I knew was not going to be acceptable. It was going to be too short a number. Your equivalent is about the number of relationships, not the length of relationships. How do you find yourself responding in those moments? I assume you’re not saying, “Time is a made-up thing and arbitrary.”

It might come off as a red flag. I’d be honest. I’d say, “I’ve only had maybe one serious relationship for about a year in college, and that was it.” The most accusatory is when a girl asked me, and she was like, “By your age, most people had 2 or 3.” I’m like, “Yes, but I’ve been spending my time doing X, Y, Z.” It’s not like I felt insulted, but I’m saying, “I’m not just sitting around doing nothing.”

“I’m not in my parent’s basement playing video games and watching pornography.” That’s the concern that she would have.

On their end, they’re trying to gauge how desirable a person I am, but if you come off defensively, that’s even worse because then now you seem like, “This is an insecurity that you have.” I would say it’s best to be honest and explain what you’ve been doing.

That’s excellent. It doesn’t matter as much what you say but how you say it when it comes to these situations. The more vulnerable and the more honest that you can be and that you can own this, the more likely that if this person is a good match, they’re going to be able to determine that because there’s no convincing someone to do anything they don’t want to do. The fact that she’s asking you this question suggests that she’s interested in getting to know you.

As I said, these are well-intentioned. I don’t think that these are bad. These are people executing a script that’s been given to them by their friends, families, society, and so on. I’d say, “I like women. I’m a bit of a slow starter. I had a girlfriend in college and it was great. When I didn’t date her, I was doing all these other things.” The other thing is I like to say, “Stop talking.” Say your piece and that’s the way it is. If she finds this to be unsatisfying, then she’s going to go find someone who has a better body count for her.

At the end of the day, I feel like I’m not at a point where I would actively try to lie. I feel like you shouldn’t lie to people you are trying to date. This is generally not a good thing to do.

I want to say this. By the way, that was a joke about body count. You can never lie to someone. This is super counterintuitive because the desire is to mislead because you want to please. The problem with that is, and again, we’re speaking heteronormative, is that women, young or old, get lied to all the time by men because these men are disguising their true intention and who they truly are because they’re trying to make a positive impression.

That’s ugly behavior. Not only is it unfair to do to someone, to be deceitful, and to mislead who you are, but it also poisons the waters. That is you are now making the world a worse place because you’re teaching this person to not trust the next person and the next person. This is the thing that is incredible, and I wish I had figured this out when I was 23.

I wish I figured this out 30 years ago. That is if you tell the truth, if you’re 100% kind but honest, that is so appealing to someone. Even if they’re not thrilled with what you’re saying, they’re like, “I can trust this man.” Being honest about something vulnerable and something that’s not the correct answer is a confident act. Going back to this idea of being desperate, the opposite of desperate is confidence.

This is one that I’ve heard from a colleague. She’s dating this guy. This guy’s into skiing. They go skiing during breaks and stuff. She’s like, “I hate skiing, but I lie because he likes skiing.” I guess this is one of the I don’t know how we rank this in seriousness, but I’m saying this goes on. You realize you’re going to spend more time doing something that you hate. This is a net negative.

She’s acting from a place of fear when she doesn’t tell him, “I don’t want to ski with you.” She’s not being her best self. He’s being misled, and if he ever finds out, he’s going to be like, “What else have you been to me about?” To be secure enough to say, “Joe, I like you. I like spending time with you so much. I’m tempted to go skiing with you even though I hate skiing. Is there a way that maybe when you go to the mountain, I just go to the local library and hang out there? You ski and I’ll meet you for a drink afterward.”

The thing about it is if Joe needs to have sex with a ski or live his life with a skier, if that’s the case, she should move on because she’ll never be able to make him happy. My guess is Joe will be like, “I understand. That’s fine. I’ll invite my buddy Phil. He’ll join me for the day and I’ll be excited to see you at 4:00 PM.”

I lived in Boulder for many years. It’s mountain biking. I remember dating a woman. I was very attracted to her. I thought we had good chemistry. On our first or second date, she was a serious mountain bike. Her job was doing PR for mountain biking. It was her life. She’s in her late 30s. She was 38 at the time. On our first date, I said, “I don’t mountain bike. I have mountain biked in the past. I’m not interested in picking it up again. I just want you to know that.”

To be honest, I’d say 50% of the reason the relationship didn’t continue past dates 4, 5, or 6 was about mountain biking because we had a mutual friend who was like, “She’s making a mistake.” When you’re 60 years old, she’s still expecting to be coming out on a bike. I think that’s fine. It’s okay to know what you want. If you need that, then you need it.

I felt like it was the right thing to do because even if I fell in love with her and wanted to spend the rest of my life with her, I wasn’t that interested in starting to mountain bike again. It didn’t agree with me enough to do that. Getting back to this idea, by the way, this is a dominating strategy. This is a strategy that works well not only for budding romantic relationships but also for long-term romantic relationships, familial relationships, friendships, coworkers, and so on. It’s to develop a reputation as someone who has high integrity and someone who doesn’t lie.

Does that always mean that you have to answer the question? My answer to that is no. For example, if a woman were to ask me, “How many women have you had sex with in your life?” I could answer that question or I could say, “That’s not something that I am comfortable talking about. It’s not something that I think is relevant.”

I’m happy to answer other questions about sexual health and so on if that’s a concern of yours, but if you’re trying to figure out whether I’m a good partner or not by the number of people I’ve had sex with in my entire life, that’s not something I do. I’m not being 100% honest there in giving a number, but I’m also not lying. Again, that’s also a confident statement to have. I own the fact that I’m not comfortable having that conversation. I don’t think it’s relevant, but I am willing to have the other uncomfortable conversations around testing for STIs, whether I’ve had an STI, condom use, etc.

It reminds me of a job interview, even though it’s not a job interview exactly. I don’t know how I’m not as adept at job interviews. I know that depending on the field that you’re in, like in the coding world, people will say, “I’m proficient in C++ Python,” and they’ll list languages even though proficiency may be something on a spectrum. They’ll put on the resume these languages and not say which languages they are competent in.

The problem with that is if I’m interviewing someone and I find out you put that you’re proficient in Python and I find out the limits of that, I can’t hire you now because I can’t trust you. I don’t know where else you’ve lied on your resume or interview and so on. This comes down to the idea that we live in a world of repeated interactions. The moment I find out someone’s being untruthful with me, I now have to question all the other things that they told me. In that way, I believe that honesty is a dominant strategy.

In general, if you’re trying to be a man, you have to be honest about yourself. That’s the very minimum.

Let’s keep moving. Otherwise, we’re going to have a five-hour show.

You have answered my second question, which is regarding the question of manhood.

I want to say this. I missed the last point about Iris and Kinneret. It is what Iris came up with, which is the most stunning standard of whether someone is an adult or not. I have the answer. I never knew it until I reset it, but the moment she said it, it became self-evident. That is this. What makes a boy a man is his ability to parent himself.

I never thought of it like that.

If you think about it, parents have responsibilities. They have responsibilities with regard to providing resources, to provide housing and sustenance, to provide security and safety, and to provide emotional support. If you do those things, you are technically a good parent. You could do other extra things, that’s fine, but those are the basics of being a parent. Parents don’t question that and they ought not to resent doing those things. That’s what they signed up for.

When you are able to do those things for yourself, you can then call yourself an adult. What that means is you’re giving up an arbitrary standard like getting married, for example, or some other standard that people use to say, “This person can adult. They can care for themselves. They can soothe themselves. They can find emotional support for themselves. They can provide for their own safety and security. They’re making good decisions about their health and well-being. Also, they’re able to support themselves. They’re able to clothe themselves and do all these things,” which means that you could be fifteen years old and an adult because you can do those things. It can mean that you can be 40 years old and not an adult, a child, because you can’t do those things.

More of my parents’ generation say, “You need to find this.” I have older male cousins who are not married and their parents will say, “I would be so sad if I die without seeing him get married because I need to know that someone’s going to take care of him.” I’m like, “He’s going to be a grown man. He should be able to take care of himself. You don’t marry someone to take care of you.” That’s weird.

Marriages were invented as a practical solution to very real problems.

Back in the time of kings and stuff, they were political or joining their alliances.

The need to partner up with a practical matter. To run a farm, you needed it. You couldn’t do that on your own, but we now live in a world where there are some people who are desperate to survive. They need to find a romantic partner to do that. I would argue that still, even if you choose to partner up as a way to create additional security for your life to build wealth and live a richer life, build a family, or whatever your motivations are, those are fine motivations. I believe that you need to be able to parent yourself to make that relationship the best relationship it can be.

It’s fine if your partner always cooks the meals. It’s fine if you always cook the meals. If you want to agree on a nuclear family with one person breadwinner and one person as a homemaker, that’s fine. What I want is that the homemaker could become a breadwinner if he or she wanted to and the breadwinner could become a homemaker if he or she wanted to.

It should be out of choice and not a necessity. It’s having the power to make your own choices to choose which one you want.

Suddenly, your partner can’t bully you. Your partner can’t unduly influence you. Now, you’re partners. You’re not a parent and child in that sense. That’s going to be a much healthier relationship for both people when you’re opting into it rather than needing it.

That goes to the whole solo mindset. It’s this power to opt into things that you want. You’re not born and placed into a moving truck thing where all these choices are made for you. You opt into things that you want to do.

It’s like your cousins. I feel bad for them in the following way. They’re getting a lot of pressure to do something that they may or may not want to do or they may or may not be ready to do. Rather than their parents saying to them, “I just want you to be happy. I realize that it’s up to you to decide how you’re going to be happy. If you believe that getting married is going to make you happy, I’m going to do everything I can to support you in that way. If not getting married is your path or delaying it is your path, I want to support you in that. However, I want you to be able to care for yourself, to be able to grow as an individual, to contribute to society, and for you to be living the life that works well for you.” It’s so funny how parents say they want their kids to be happy and then they say, “My kids are going to be happy if they do the thing that makes me happy.”

It’s like, “My kids can be happy when they’re a doctor or can buy a house,” or stuff like that.

I have a friend. He’s a full professor, tenured at an elite university. It’s one of the best universities in the world. His dad, who’s the doctor, still is a little bit disappointed he’s not a medical doctor. It’s like this guy is climbing the mountain. He has an incredible wife. He’s got these fantastic children. He’s healthy. He’s happy. He’s all these things, and there’s this little tiny tinge of like, “It’s too bad he didn’t get an MD.”

That sucks because you’re the person that has to live with the consequence of your actions. I know a lot of people who are young Asian Americans who feel a lot of pressure from their parents starting from a young age to achieve a certain number of things. That’s why I guess there’s this whole stereotype of them being these workaholics in high school and stuff like that. At the end of the day, you’re going to have to live with the consequences of your own actions.

I have a friend who, throughout high school, was tough on herself. She was valedictorian of our high school and graduated with a Computer Science degree from Berkeley, which is a great program. In the end, she decided to pursue acting and other creative endeavors because she said, “I went through all of that and I hated every second of it. I have to live with the consequences of my own actions.” I thought that’s even more admirable than sticking it out because you’re opting to go against the grain and choose for yourself.

She sounds like a solo. Good for her. It’s true. A very adult thing to do is to say, “I’m going to live with the consequences of this.” What’s your third question?

My third question is what kind of resources would you say you have for people in my position who want to develop themselves and try to develop their own definition of manhood? There are a lot of advice online that range in usefulness.

What stood out to you as something useful? Is there something off the top of your head? This is a question that a lot of young men ask. I asked it of myself when I was about the same age as you, and I found the resources to be undesirable. There were a lot of GQ, Esquire, and these men’s magazines that taught you what whiskey to drink or what watch to wear. I found that they didn’t tackle the problems that I thought I was having, which is, “How do I develop into a better person and not a better person from a consumption standpoint?”

I’ve seen those things going around online where you should dress a certain way or make sure to wear a certain kind of clothing or something like that. Generally, they are very superficial things that don’t solve the problem. They mask up or make you feel like you’re changing something when you’re not.

I will say this. Some of that advice is useful in the following way. That is, if you’re going to be able to parent yourself, you should be able to groom yourself. You should know how to make an appointment to go to the dentist every 4 to 6 months to get your teeth cleaned. You’re going to get to a certain age where you have enough self-awareness that you realize that you have nose hairs that are sprouting out and distracting the world.

I often buy a nose hair trimmer from my friends in their 30s who are missing this distracting element of their looks and so on. You should learn to buy clothes that fit you and that look good on you and so on. Also, to be able to present well. That’s more the symptoms of making this transition. It’s not the most essential element to it. If you go online, there’s a lot of toxic stuff out there, the red pill manosphere types.

What’s unfortunate is that a lot of the men who should be giving this advice are not because men are so unpopular now, that to be pro-man can be simultaneously interpreted as being anti-woman. I don’t believe it’s zero-sum. When men are better, it helps everyone. When men are doing well, we live in a world that has less violence. It’s a world where there’s more invention. You have better fathers, brothers, and sons. You don’t have this toxic masculinity that’s there, this hateful, angry, misogynistic element that can come out of this.

Even to look for advice, it also feels a bit weird because it doesn’t matter. “You’re supposed to already know how to do these things. Why don’t you already know how? You’re not supposed to be having a hard time. You’re supposed to be strong and know how to handle everything already.”

One of the troubles with the patriarchy is that it says this. “You are supposed to be in charge. You’re supposed to be powerful. You’re supposed to be these things,” and this can even get enforced by women, where a woman’s like, “You need to man up here.” It tamps down men’s vulnerability in a sense. Admitting that you don’t know what to do and admitting that you’re struggling is, for some people, the antithesis of manhood.

We’re shown warriors, gladiators, and heroes. These are people who are impervious. They’re strong and powerful. They’re unaffected. Those are mythological creatures. They’re made up of people. The manosphere types, the red pill types, first of all, are often ill-informed about things like evolutionary influences and biology. They don’t understand cultural anthropology. They’re not well-read, and they don’t understand these kinds of things.

They have enough rudimentary knowledge to seem like they know what they’re talking about. They’re also disagreeable people typically. It’s because you need to be disagreeable if you live in a world where you’re trying to support men, and it’s seen as hurting women. If you take this zero-sum view of the world, which is that if men are doing well, then women are doing poorly. It becomes very easy to make that case, and then these guys are like, “I don’t care what you think. FU.”

The men who are more agreeable often don’t want to wait into that. My experience with it was solo originally was going to be for bachelors. It was going to be The Bachelor’s Guide to a Remarkable Life. I remember testing various titles and various descriptions. I would get a subset of comments that read, “I need to listen to this show. This sounds like it would be misogynistic.”

However, there was nothing in the descriptions that would have suggested that. It was assumed because it was designed to help men that it was also simultaneously going to hurt women. I decided not to do it in part because it didn’t make sense to limit the help to one gender that was there. I didn’t have a good answer to this question, to be honest, because there aren’t many good resources. There’s not a book I can give you that the title is How to be a Man. I’m sure that a book exists, but it’s going to be a bad book.

What I did was I asked some male friends their reaction to this question. I’m going to curate a few of the answers here. The first one was related to learn to parent yourself idea. He writes, “The things that used to be true about being a man aren’t true anymore, namely, the John Wayne and Ronald Reagan archetype. We’ve come to learn that this path is unhealthy, misogynistic, and an artificial construct.”

“The best men are the best people. I’m not sure it has much to do with gonads. The men I admire most are those who are loyal, kind, and responsible. The same is true of my favorite women. The real contrast isn’t between men and women but between men and boys. Make a list of the characteristics of boys and then endeavor to outgrow those.” I’ve got goosebumps reading that. I think that is stunning advice. A boy is petulant. A man is not. A boy is insecure. A man is not. A boy is mean. A man is not. You could you can imagine that list. It includes these things about parenting himself. A boy has no way to make his way in the world. A man does.

I never heard a phrase like that. I heard, “You’re supposed to be this,” but what people mean is you’re supposed to outgrow all those insecure and petty behaviors that you do as a child. People don’t phrase it that way. People phrase it differently.

If I were you, in my journal, on a sheet of paper, or whatever, I would write those elements of you as a child or of children in general and get honest with yourself and say, “Is that me?” If the answer is yes, now you have a guide. Whatever that problem is, now you know it will go, and start working on it. You then can start to find the specific solution. For example, the mean one is very real. The angry young man trope is very real and gross. The angry young man does not make the world a better place. He’s not a good friend. He’s not a good son. He’s not a good lover. He’s not a good boyfriend. He’s not a good supervisor or supervisee. If you’re not careful, you grow up, and now you’re an angry old man. That’s even worse.

I’m going to stitch them together, but a few of them made the case to live life boldly or to live a remarkable life. One person wrote, “I’d suggest that the best resource is ‘life’ as that is what teaches you the best lessons. Travel, exercise, take chances, live and love intensely. Own your mistakes and learn from them. Be better today than you were yesterday. Ask supervisors, friends, family, and lovers for feedback. Be confident and humble all at once.”

I have another one to add, but as I was reading that, I thought about that question that you got on that date, which is, “How many relationships have you had?” A perfectly appropriate response along these lines is to say, “I’ve had one girlfriend in college, and it’s wonderful. It didn’t work out. I’ve been single ever since. If that’s too few for you, I understand, but if it’s not, I’d love to explore getting to know you better.”

It flips the question like, “Is it too few for you?”

If it’s too few for you, I understand. We can be friends. We can finish up the date here and have a nice time, but if you’re open to dating a guy who’s only had one girlfriend, I’d love to get to know you better.

I like that answer also because it shows that there are no hard feelings about it. Everyone can have deal breakers if they want.

If you need to have 2.5 girlfriends for it to be okay to date, that’s fine. That’s up to you. I won’t be the right guy for you for another one and a half girlfriends. You could even say to her, “If you need me to have a couple of other girlfriends, I’ll call you in a couple of years. We can meet up then.” Another friend wrote, “Study shows that reading fiction and not nonfiction is what teaches people to empathize with others’ points of view. Write about yourself. Journal. Live somewhere weird. It’s too on the nose to read up on what it means to be a man. The answers come experientially.”

That’s quite good. I’m going to end with one of my own. I would encourage you or any young man reading or old man for that matter to start having conversations like this one. Get in the habit of talking to your male friends and your female friends. If you don’t have any female friends, get one. Learn to go deep. Learn to be vulnerable. Learn to say, “I don’t know.” Learn to say, “I’m scared.” This keeps coming up in episodes. There’s this question that scientists ask. They ask us, “Do you have someone to call in the middle of the night when you’re sick or afraid?”

I’ve heard of that. “Do you have someone close enough or a friend that you could depend on?”

My heart breaks for the person who can’t answer yes to that question. What’s so important about that question is the term afraid, like if you’re afraid. It’s okay to be afraid. Part of being human is to be scared and uncertain about things. Too often in that John Wayne and Ronald Reagan archetype, you’re not allowed to say you’re afraid. You’re not allowed to say, “I’m uncertain.” You’re not allowed to say, “I don’t know.”

Learning to have conversations with people where you’re allowed to be vulnerable or where you’re allowed to develop both a masculine and a feminine identity within yourself is that you can have this confidence and this assertiveness, but you can also have empathy and sensitivity. Also, you can decide when to draw on one or the other as needed. The problem is too many men think that being a man is about being assertive and confident and being tough and macho.

I do believe that that is part of being a man where you can take care of yourself. If you find yourself in a dark alley squaring off against someone, you feel like, “I’ve got a chance here.” Also, if you encounter a bully at work, you’re not going to be bullied. Having that as a skill is an important skill to be able to have.

When I talk to young men, I unilaterally encourage them to lift weights. I was like, “If you don’t lift weights, you should start lifting weights. I think you should work to start lifting heavy weights or to start deadlifting.” It’s because that is a way to build your body. It’s a way to develop confidence, and it’s one that will pay off if you do it in your entire life, not only when you’re 23 or 53 but when you’re 83.

However, if you are only confident, if you’re only assertive, or if you’re only strong, you’re limited in terms of the repertoire of skills that are necessary to have, which is, for example, you often don’t even need to fight because you can say to someone, “It seems like you’re upset. Is there something that I did that upset you?” You can be accommodating and sensitive. You can be empathic to be able to say, “I’m sorry. I did not mean to do that.”

You can be gracious and you can avoid conflict in this other way. A good place to start to be able to develop those skills is in these vulnerable conversations with people who are close to you and who are not going to judge you harshly for making a mistake. They’re not going to think there’s something wrong with you because you’re sad, uncertain, or scared in a sense. The feminine side is much better at that than the masculine side.

If I have a problem, I have a couple of close guy friends with whom I could talk about struggles and stuff like that. They’ll say something like, “I’ve been there before.” I’m like, “You’ve been there before. I thought I already figured it out and I’m the only one.” I’ve talked to some friends, and then I’ve heard that having close women friends is like they’ll tell each other everything. Whereas with close guy friends, from what I’ve experienced, maybe it’s not the same. At my age, it’s not exactly the same.

It’s very hard. I have deeply intimate conversations with both men and women in my life. I was lucky as a young man because though I lacked the skills to have a girlfriend, I was very good at creating friends. I had lots of female friends when I was a young man. That was beneficial to me because I didn’t feel like a leper. I might not have been having success with women, but I’m like. “Women don’t think I’m gross. They like spending time with me.”

They may not want to have sex with me, but they’d like my company. There is a woman that I worked with. We were resident advisors. Her name was Sophia. I’ve lost touch with her. I would love to figure out where she is to send her a little thank you note. Sophia and I would go to the local alternative dance club in New Brunswick, New Jersey at Rutgers and go dancing. Sophia was beautiful. She was sophisticated. She was well dressed. I was a little bit of a schlub.

I didn’t dress very well. I didn’t feel like a very attractive man. I was a fit guy. Sophia liked that Friday night or Saturday night. I’d wander down to her room and say, “Do you want to go dancing tonight?” She’d be like, “Yes. That would be fun.” It was never romantic. It was never sexual. We enjoyed each other’s company. We go on this walk down there and have a great time in a way that we wouldn’t have otherwise if we had stayed in that night.

That was good for me because it was like a girlfriend adjacent in a sense. I got to develop my skills and I got to talk to her about what was going on in my life. I got to have her perspective on things. I got to have an experience that I would have been unable to do. I would never have gone to that dance club. I needed her. She was my shield.

She gave you the confidence to do something that you otherwise probably wouldn’t have had the confidence to do.

I made her laugh and we had fun. It is about trying to cultivate those kinds of relationships where you get to be able to express those two sides of yourself. You also get to welcome those two sides of another person. I have a few male friends in my life who have almost the perfect balance of masculine and feminine. They are the best men in the world because they have a bigger toolkit than the average guy. I strive to try to have that too and to emulate that.

That’s good. I’m going to write it down and apply it more in my life. I feel like I have like a good number of women friends, but maybe it should be more normalized for guys to talk about things that are like this on the show. As a young guy, it’s friendly competition sometimes. “Have you done this?” in whatever sphere like getting a job, internships, or vacations and cool things you’ve been doing that’s not so normalized to be normal yet, but I feel like that should change.

I talked about what makes a good friend, and it doesn’t matter the gender. That is the person who provides value in your life. There are lots of ways they provide value. They’re fun. They’re funny. They’re a good company. They’re smart, whatever that is. Different friends provide different types of value, but they’re appealing and you’re mutually appealing to them. That’s number one.

Number two is they are of high integrity. That is they’re honest with you. They’re reliable. You can trust them. You can tell them your secrets and they’re not going to talk behind your back. You can trust them and they can trust you. The last one is that they practice compersion or what that translates into anti-jealousy. That is a good friend celebrates your successes and commiserates your failures.

That means that if you get a promotion, a good friend is like, “Let’s go celebrate. I’m so happy for you.” It doesn’t diminish him or her that you got a promotion or you got to go to Bali or whatever the adventure you got to go on. Moreover, when you’re taking a loss, when you’re sick, you hurt yourself, you get fired, or whatever it is, they say, “It sucks. I’m so sorry to hear that. Is there anything I can do to help?”

I’ve never heard that word before, compersion.

It comes out of the polyamorous community. It’s often around jealousy, sex, romance, and so on, but more generally, it applies to this idea of the opposite of jealousy, anti-jealousy. The issue is this. The difference between a friend and a frenemy is anti-jealousy and jealousy. It’s because frenemies are unhappy when you get the raise and they’re happy when you get fired.

That’s funny. I never thought of it like that, but that’s true.

If you think someone’s a friend or a frenemy, you have to do the thought experiment, which is, “If their girlfriend dumped them, am I going to be sad? Am I going to be happy?” The way I feel is like, if your girlfriend dumps you, what I asked my friend is, “How do you feel?” If he’s like, “I’m happy,” then I’m happy. He’s like, “I’m sad,” then I’m sad, and that kind of thing. That’s the standard that I use. I am ruthless about my friendships in that way.

That is I demand that behavior of myself and I demand it of other people. I had a very tough conversation with a friend. I caught wind of something that seemed to be a low-integrity thing that he had done that involved me. I had to talk to him about it. Things felt tenuous with regard to our relationship as a result of that because I said to him, “If this is true, what else is true?” Daniel, how are you feeling about our 30-year age gap in this conversation?

It’s not like people say, “When you get to a certain age, then you’ll understand.” I feel like maybe people might be capable of understanding this. The concept of living a high-integrity life was like, “People never told this like explicitly in this way.” I guess I’m pleasantly surprised that a lot of the take-home actions of the wisdom between the age gap is pretty easy or maybe simple to apply. You have to live a high-integrity life and stay true to yourself. Also, try to be a great person to other people.

The thing about it is that it doesn’t get taught. Because there’s no book on how to be a man or how to be an adult or whatever the name of the book is going to be, you often learn these through experience, and that’s why age correlates with wisdom, but it doesn’t need to.

People will learn not to lie because they face the repercussions of that because you could be told, “Lying is never the move. It will only result in negative consequences.”

It makes the world the worst place, in general. Even if it helps you at the moment, it is a long-run poor strategy. I’m glad you could learn from my mistakes and from my slow ability to learn my late bloomerness, etc. This has been incredibly helpful for me. It was useful for me to reflect on how far I’ve come. It allows me to be a little bit celebratory about how good my life is, how comfortable I am with who I am now, and how uncomfortable I was many years ago. I’m glad that you have access to more resources than men in 1993.

I appreciate this conversation because a lot sometimes is overwhelming where you get advice from when you’re hearing all sorts of things that you know are objectively not the way to go. I appreciate you being straight with me. “This is what matters in life.” People try to get these things in different ways, but honestly, you have to go to the basics of being the best person you can be.

Daniel, I’m optimistic for you. The fact that you’re asking these questions and the fact that you have been so gracious in this conversation, I appreciate it.

Thank you so much.



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