Friday, 28 August 2026

In Defense of Dating Boring Boys.

 

 {from Waylon’s forthcoming Self-Help is Bad for You}

In Defense of Boring Boys (or rather Gentleman, and Women).

“I slept and dreamt that life was joy. I awoke and saw that life was service. I acted and behold, service was joy.” ~ Rabindranath Tagore

The “other day” someone posted an article entitled “Date a Boy who Travels.” I agreed with a lot of it, and I hated the entitlement in it.

Don’t date a boy who’s selfish.

Don’t be selfish.

Just as dating is fun—but it’s also full of disappointment, and trying yet again—relationships may involve moments of pleasure and happiness, but they’re about growth and service.

“Date a Boy who Travels”?

Date a man. Date a woman. Date a grown-up, as defined by the capacity to be accountable, to listen, to be defeated and learn and grow out of said defeat. ​

Date someone who’s willing to look at themselves, willing to see co-dependency for what it is. Who views a relationship as a vehicle for caring and activism, not an escape from it; as a vehicle toward growth, not a battle to be won.

It’s less important to be right than to be in reality.

~

“Date a Boy who Travels.”

She shared it up on her social media.

“Love this,” she noted. It was romantic.

I do get it.

We all like the idea of dating Indiana Jones, or one of those six-packed hunch-backed hottie climbers from the gym who’re always coming back from France and heading out again for Hueco Tanks, or Yosemite.

And, to be fair, I liked a lot of the article: the un-materialistic parts of it. The parts that extolled the virtues of letting go, simplicity, Nature, independence within relationships (as with my essay on the Buddhist notion of Love, and how it’s not selfish, you know)… and being world-aware, while appreciating home base.

But the whole Bucket List Thing has always seemed a bit…off.

Twisted at its roots.

It’s a bit of a Capitalistic overlay on top of this beautiful world of ours. It’s materializing adventure and splicing life’s most precious memories and simple joys in with influencing and algorithms.

It’s consumptive, it’s acquisitive, it’s patriarchal in the conquering sense rather than appreciative, open, present, boring, peaceful.

But I do get it.

And if the world were alright, sure, I’d say: YOLO, bro.

Go for it: date a boy (or man, or woman, or other) who lives life for pleasure. For adventure. There’s nothing selfish about pleasure that doesn’t cause others harm. But, in reality, such a life—the endless carbon footprint, the space-filling notion of living life to the fullest…leaves a plastic-wrapper-strewn trail in its wake.

“Date a Boy who Travels”?

That’s nice if your life is about pleasure. But there’s a more exquisite joy.

As my best buddy, a cyclist and youtube star, says, “Most adventure dudes are so selfish…they don’t care about much more than getting to tops of mountains and doing gnarly sh*t.”

I say “f*ck it” to the bucket list. The world isn’t alright.

It is wondrous. It is amazing. But it’s also full of suffering. It’s overheating, insects and birds and animals are dying, it’s drowning in our plastic, it’s heating up. The time immemorial rhythms of Nature are breaking up, falling apart.

The true man to look for takes care of others, and himself.

The true patriarchy is to be found not in casual misuse let alone abuse; but in responsibility, and care. That is the only real kind of fun—a kind of fun that’s fun for all, including the next seven generations.

This is a time for heroes. Ordinary, everyday heroes dedicated to service, to kindness, to generosity.

This is a time for the luckiest among us not to merely travel (as a way of life), but rather to serve (as a way of life).

“Date a boy who travels because he’s not blinded by a single goal but enlivened by many,” urges the author, in “Date a Boy who Travels.”

I beg to differ, my friend. Being “blinded by a single goal” is perhaps a fair definition of entrepreneurship, of teaching a classroom of impressionable children, of achievement generally—or even of parenthood. Any great ambition requires focus, dedication, sacrifice, perseverance—single-mindedness.

It’s typical of each generation to exhort ourselves to “Date a Boy who Travels”, illustrated with a happy-happy-joy-joy pretty Pinteresty photo of a boy and a rucksack and a dream. It’s #instaromantic.

But you know what’s truly romantic?

Date a Boy who Serves.

Date a boy who wants to do some good, to put others before himself, to help others who haven’t been given the same opportunities. That’s f*cking hot.

Awhile back, I joined my friend Duzer—we served as bartenders (boytenders, we called it) for a non-profit called Intercambio. The founder is a young man who has dedicated his life to providing a bridge for immigrants, to learn English. That’s my kind of Boy.

Date a Boy who’s big enough to think about Others First. Am I right?

I look at Malala, or Greta, or Attenborough, and Goodall, or Mister Rogers or Miss Rachel—and I admire them. Let’s admire folks for their willingness to give so much up of their own private lives to serve because they know they can help many more. Let’s hold up as bad-ass heroes those who demonstrate a willingness to jump into the mud—into a path of service that few of us seem willing to jump into.

This day and age requires heroes who can help underprivileged children get bicycles, like Duzer. Heroes who create an ecofashion line that employs women with HIV in Cambodia. Heroes who head up a mine-defusing operation in South America. (Why not travel, and serve?) And, yes, heroes who sit, bent over a cup of organic coffee, working on their laptops for years and years and years and years. It might look boring, compared with strolling the streets of, say, Beijing—but as Confucius or Mark Twain reminds us,

“Choose a job you love, and you will never have to work a day in your life.”

I take exception to that “Date a Boy who Travels” because we can do better.

And if we can do better, we must do better. This is an urgent era.

We must remember to admire the teachers and servants among us: those who are quiet and humble and brave and confident enough to do what might be boring. To work hard, knowing that their service might help this world to heal, and flower. Because there’s nothing sexier, after all, than dating a boy (or girl), or rather man or woman who thinks of others before his or herself.

But there’s a catch: dating a girl or boy who serves requires sacrifice on our part, too.

Because we’re not the priority. Our love can not be merely selfish, about itself.

We have to learn independence, if we don’t already know it. We have to remember our own lust for our own life and service.

But that’s the ultimate gift—remembering our own path of joy is far sexier than scrolling through someone’s Instagram adventures.

Date a Boy who Serves: while he may not be prioritizing that bike tour through France or surfing adventure down in Costa Rica, he will be eager to get out of bed in the morning, and reluctant to close his eyes at night. A boy who serves will sometimes say “no, honey, I can’t go with you. I have to work.” He might say that a lot. But what he means is, “honey, it’d be fun. But fun isn’t my priority. Service is my ultimate fun, even if it looks boring.”

So I say let’s stop reading, writing or sharing pretty inspiring things about travel and pleasure.

Let’s start writing, sharing and living boring, beautiful, fulfilling lives of service.

Let’s start dating Gentlemen, and Ladies—not just boys or girls. We can have our cake, and eat it too: we can, and must, work hard to be of benefit—and we can (mostly) enjoy being of service, together.

“I could not love thee, dear, so much,
Loved I not honor more.”
~ Richard Lovelace, English poet


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