The Bachelor’s Way
“The only really happy folk are married women and single men.”
H.L. Mencken
I often reflect upon the changes in my life over the last four years. I discussed in this previous newsletter why I am here; for this one, I will dive a little deeper into what being a middle-aged bachelor in America looks like for me.
I mentioned in my last newsletter that “monogamy felt stifling.” I know this is a sentiment some men can relate to, and I also understand that some men crave the feeling of being a part of a committed and monogamous relationship. The difference between the two preferences is often a matter of timing rather than destiny; I think it’s natural for this preference to change for a man. And it does seem this lifestyle is replete with former players who eventually settle down, drop out, or go deep into religion. Having said that, I cannot fathom agreeing to monogamy at this time of my life; it would feel like a sacrifice rather than something to celebrate.
There is no one-size-fits-all all to the question of singlehood vs couplehood. But society is designed and expects couplehood; to do anything different is viewed as unusual, less desirable, and outside of societal norms. I did not appreciate the extent that societal programming pushes all of us towards couplehood until I went bachelor mode; I now frequently field questions about when I plan to “settle down,” even from men who want to hear about my latest dating escapade. Just last night at a club meeting, a friend said it must be difficult for me to find companionship; he looked confused when I laughed and said I did not struggle with this.
“Bachelors themselves constitute a nonconforming minority group because, by crossing the lines of acceptable individuality, they too do not accede to what is believed to be the natural order of things.”
Howard Chudacoff, The Age of the Bachelor
There are clear financial benefits to marriage, although my financial well-being demonstrably improved once I went bachelor, to a great extent because my only dependent now is my daughter. Let me be clear that a girlfriend becomes a dependent. There are also claimed health benefits; however, that article is delusional - I’ve been married and coupled, and my life is measurably better in all five of those areas now - and the better sex life is a complete lie. That article is an excellent example of the assumptions society makes that support the notion that couplehood is better.
To many, we are not deemed to be adults until we are married. To quote Howard Chudacoff again: “Though the emphasis on marriage may have varied in intensity according to time and place, even so-called primitive societies have made the link between adulthood and marriage explicit and strong.” The lack of male initiatory rites to signify crossing the bridge from boyhood to adulthood is well-documented. For many men, marriage is the only rite of passage they will experience. However, this particular rite of passage comes with a price for men. Again, quoting Howard Chudacoff: “The truth is that marriage is originally contrary to the instincts of men. They have to conquer certain tendencies within themselves, fierce and independent traits of their nature, to accept the role of husband.” I had no appreciation for this when I first married nor when I committed to a long-term relationship. It is now very obvious how much I would feel like I am sacrificing to do either.
“If we did not look to marriage as the principal source of happiness, fewer marriages would end in tears.”
Anthony Storr, author of Solitude: A Return to the Self
I think an under-appreciated societal expectation is that we will hop on the Relationship Escalator and ride it to the top. Anything outside this relationship model bucks the assumed progression: dating - exclusivity (monogamy)- commitment - merging - partnership. There is an increase in social status that is bestowed on partnership; a couple is deemed greater than a single person. To quote Howard Chudacoff again: “Since the late nineteenth century, the corporate and organization of industrial and postindustrial capitalism has put a premium on cooperation and unity. Though the society ostensibly appreciates individual initiative, it constructs moderate limits to individuality and imposes penalties on persons who exceed those limits.” One of the realities of escalator-type relationships is they take priority over every other relationship in a person’s life. This felt natural to me while I was married and coupled, and now the whole concept feels stifling; I cannot imagine ever again allowing this to happen again.
There are other under-appreciated costs to being in a relationship that author, college professor, and bachelor Peter McGraw discusses in his new book Solo, Building a Remarkable Life of Your Own. The first is opportunity cost. “Spending money, time, energy, and attention on one thing means it cannot be spent on other things. The opportunity costs of the traditional, long-term relationship, especially marriage, are substantial because the escalator requires maximum attention and support - a partner and kids are everything.” The opportunity cost of a relationship isn’t worth it for me at this time in my life; I would have to sacrifice time and resources to support a relationship I am unwilling to part with.
The second he discusses is optionality. Optionality “is the value of having the ability, but not obligation, to make choices.” In other words, the freedom to choose or not to choose; single people have a much higher degree of optionality than coupled people. This is an area of my life I feel I don’t use to its fullest potential. I can get stuck in a comfortable routine at home when the reality is I could decide on very short notice to get away for a night or two almost whenever I want. Peter nicely sums up these two concepts by stating, “Singles have greater optionality and fewer opportunity costs.”
Peter McGraw communicated concisely what I have been saying about myself for quite some time: I am at a time and place in my life where I want maximum freedom and flexibility and minimum responsibility or obligations. Furthermore, I am jealously guarding my most precious resources of time, attention, and finances.
Choosing bachelorhood may be one of the original “unconventional” lifestyles. Before the publication of Playboy Magazine in 1953, bachelorhood as a lifestyle was looked at as liminal, a period between boyhood and manhood. Hugh Hefner said, “The notion of the single man began in the 1950s. The idea of the bachelor as a separate life was new and obscure.” This was especially true in post-WWII America, where conformity, family, and “Father Knows Best” were celebrated. What started slowly in the 1950s accelerated in the 1960s with the sexual revolution; men no longer had to marry to get access to sex. And the archetype of the Space Age Bachelor was born.
“A bachelor is a guy who leans toward women – but not far enough to lose his balance.”
Earl Wilson
To be a bachelor means to go against the grain and recognize that what is good for society may not be suitable for the individual. Not necessarily libertine, but more libertarian than conformist. And in a culture that feels increasingly feminized, bachelorhood becomes a rebellion, embracing masculinity and its quest for freedom, be that sexual, financial, or spiritual; choosing to live life on your own terms; to look at your life as complete as a solo man; taking responsibility for what I think comprise the foundation of a healthy life - physical, mental, emotional, spiritual, and financial - and having a community of friends and professionals who support your foundation.
David Deida discusses the masculine’s quest for freedom in his book The Way of the Superior Man. “The masculine is always seeking release from constraint into freedom. The feminine often doesn’t understand these masculine ways… The breakthrough into freedom, however it occurs, is the main motivation of the masculine…The typical masculine desire for freedom involves the feeling of death, which is the ultimate masculine fear and freedom…The capacity to face death for the sake of freedom, whether actually in war or ritually on the football field or chess board, is the ultimate masculine act, evoking men’s deepest emotions.” The masculine seeks to break through the fear of death to the other side, where the ecstasy of spiritual freedom exists; this is our highest calling. This is the calling I didn’t understand when I was younger. I thought maybe I’d find it in the likes of drum circles and mythopoetic archetypes of Iron John. Then, it was men’s groups that I found after reading No More Mr. Nice Guy. And, of course, therapy. All these efforts improved my life and were necessary steps for me on my way to fulfillment. However, this last step I’ve taken over the past four years of being single, going through my dark night of the soul, which was my spiritual death, and breaking through to my ecstasy of masculine spiritual freedom, has transformed my very existence.
Freedom is a rare topic in this corner of the internet. Many blogs discuss dating and relationships, but very few discuss the benefits of living an unfettered life. And I think that’s because true freedom is hard - it requires personal accountability, discipline, and living outside the normal bounds of society. True freedom doesn’t simply happen; it takes work. Unfortunately, there’s no shortage of negative content about how awful women can be; maybe that’s because it’s easier to create an “enemy” than it is to embrace freedom for its own sake. I’m far more interested in being the best version of myself, maximizing my freedom, and leading a remarkable life than I am in all that negativity. Sure, there are shitty women, just like there are shitty men. Don’t let either one into your life.
One of the unexpected yet profound changes that has happened to me over the last four years is that I experience far more consistent happiness now than at any previous time in my life. This isn’t to say I’m always happy; I don’t have that personality type. I’m pretty intense and can have my moods. Having said that, I’m more often happy than not. I attribute this to minimizing drama (hard lesson about that here), maximizing optionality, having sexual variety, increasing my financial well-being, leading a healthy life, sharing time with family and friends, doing things I find fun and enjoyable, focusing on personal growth, and not having to negotiate these things with anyone. I value these things, and I think living a life in harmony with your values leads to long-term happiness. These things I value are more significant than any woman; were I to give up or compromise on them for a woman, they were never something I truly valued.
Something I love about my bachelor lifestyle is living by myself; occasionally, my daughter stays with me, but most of the time, I’m on my own. My home is my sanctuary where I recharge my batteries and guests feel welcome and comfortable. My art, books, family photos, and music surround me. The decor is all mine and is a true reflection of my tastes. My one-car garage is full of motorcycles, and my bed is incredibly comfortable and is reviewed by my guests as being so. I have a ridiculously large bourbon collection. I enjoy cooking, and my kitchen has my preferred pots, pans, and utensils. I entertain and host parties, and I don’t need to ask permission or coordinate with anyone else’s schedule. My home is my “mancave,” and I will never settle for anything less ever again.
There’s been a lot of emphasis in modern culture on self-care and self-parenting, and I’m guilty of occasionally using those terms myself. But I think these modern terms all boil down to taking care of your shit and taking care of yourself; in other words, being self-sufficient. And I believe this and being comfortable being alone are the two central traits that a bachelor must develop. An extrovert’s version of being alone will look different than an introvert’s; whatever it looks like to you, get comfortable with it. Otherwise, I think there’s a risk of falling into a relationship out of loneliness or boredom. I firmly believe a relationship should be intentional; it’s better to be occasionally lonely or bored than married and miserable!
Marriage and relationships require compromise and, to some extent, a go-with-the-flow mindset. Culturally, there is far more emphasis on “happy wife, happy life” than masculine happiness. That’s not to say men can’t be happy in a relationship, but the cost of that happiness is masculine freedom. Bachelorhood is the opposite: a life without compromise and full of masculine freedom. And I’m not willing to compromise on this.
It’s evident from reading my blog that I enjoy the company of attractive, intelligent, and agreeable women. Lately, they have become an interlude rather than a focus in my life. I appreciate their company, but I no longer focus on filling my social calendar with their company. I currently have two on rotation at home, which is plenty. I keep them at arm’s length; they don’t meet my daughter, and I don’t see them more than a couple times a month due to my travel schedule. This works for me; what works for you could look completely different. The essential element for dating is to actively manage it rather than be a passive passenger. Know what your goals are and stick to them; it’s pretty easy to get sidetracked when it comes to women, dating, and sex.
And then there’s irony. Much dating advice centers on creating an attractive and exciting life to draw the attention of the kind of women you want to date. You do so and then discover that your life brings you so much satisfaction and happiness that there’s no need or time for a partner. This is where I am, and that feels like a victory.
I’ve covered a lot of ground in this newsletter. I’ve attempted to distill some of the themes, concepts, and ideas from previous newsletters into one place. This may be a work in progress; I’m still finding my way here.
To summarize, I think a prerequisite to fully and deeply enjoying bachelorhood is to embrace it as a destination rather than a liminal time in life, and I think that requires embracing the masculine quest for freedom. Self-sufficiency, comfort with your own company, staying true to your values, and taking responsibility for the foundation of a healthy life - physically, mentally, emotionally, spiritually, and financially - and having a community of friends and professionals who support your foundation. And guarding your most precious resources of time, money, and attention.
“A Bachelor of Arts is one who makes love to a lot of women, and yet has the art to remain a bachelor.”
Helen Rowland
Thanks for coming along.
Peace, Freedom and Progress