Find Your Goofball
Romantic love is not a prize awarded to the best in class.
For a few years in the mid-2010s, I was introduced on podcasts and interviews as a “dating expert” because I published a book for single women. The label never quite fit, since my book is less about dating and more about navigating the morass of toxic advice and attitudes our culture dumps on single people.
I was single and dating in the 1990s and early 2000s, an era when Monica Lewinsky was a punchline and The Rules was a bestseller. The world wasn’t kind to young single women, and we were perpetually assaulted by smug voices asking if our brilliant careers were keeping us warm at night. Good times.
Men were in the power position, and if we wanted to marry one we had better buck up. Go to the gym, wear stylish clothes, see a therapist. Dating guides taught us to see ourselves as commodities; being desirable meant polishing and pruning ourselves and creating an illusion of unattainability. I could never watch The Bachelor; I felt like I was living in it.
Dating guides insulted women, but they also insulted men. If you were a reasonably put-together woman with a good job and a nice apartment, you invariably got the feedback that you were too intimidating. Men had all the power, but they were also hothouse flowers, terrified of any woman who could mow her lawn or fix a leaky faucet. They were also presented as interchangeable widgets, and the strategies for attracting them were uniform edicts about not being too critical and having long hair.
It was horseshit, and on a certain level I always knew that. But it can be hard to remember when you’re spending another Saturday night alone.
I took down my “dating expert” shingle many years ago—which, by the way, any person who has been with their partner for more than a decade is required to do—but I’ve been fascinated by the recent conversation about “heteropessimism,” particularly where it pertains to young single men. The power dynamic appears to have flipped, and now young men are the ones urged to revamp themselves in order to find love.
I’m not talking about the really toxic manosphere stuff like the guys in the Louis Theroux documentary, or the men delivering “pickup artist” type advice on how to be an asshole. I’m talking about advice coming from decent men who voted for Kamala Harris and want to help men find lasting, grownup relationships.
Scott Galloway is an author and marketing professor who speaks to and about young men from a center-left viewpoint, sharing his views on CNN, MSNBC, the PBS NewsHour and many popular podcasts. He has often said that as a white, male baby boomer, he was born on third base—that he has, in his words, “unearned advantage.” He applauds women’s progress in the workforce, and condemns men who blame women and people from different racial and ethic backgrounds for their problems. So far so good!
Galloway frequently appears on podcasts where young men are the primary audience, and I’m glad he’s telling them not to blame immigrants for their problems. But when he talks about dating and relationships, he takes the same scolding tone that single women have endured for generations. Young men, he says on Lewis Howe’s The School of Greatness podcast, need to “level up”:
Are you in shape? Do you have a plan? Are you kind? Do you demonstrate artisanship and interest in different things? How do you demonstrate excellence?
If you’re confused by what it means to “demonstrate excellence,” Galloway gives an example on Chris Williamson’s Modern Wisdom podcast (a clip I listened to via Chris Kavanagh and Matt Browne’s delightful Decoding the Gurus podcast):
The highest target-rate success environment is if you can get a group of friends together that are very impressive and invite a romantic interest. And she sees you have impressive friends, right? She’s gonna be into you. … A cool posse? There is no bigger turn on for someone than, “Look at who this guy rolls with.”
The problem is, if you view your friends as instruments to increase your chances of getting laid, then … you probably don’t have many friends.
Galloway is even weirder when he talks about kindness. He tells Howe:
The most underleveraged secret weapon in mating for a man is kindness. As women instinctively believe at some point they’ll be vulnerable because of gestation, or they’re physically smaller. So they’re very drawn to men who demonstrate kindness, and that is acts of generosity with no reciprocal expectation.
Throughout his advice-giving, Galloway sounds like an alien reciting an instruction manual for how to be a person. He admits that in the past he viewed relationships as transactional, but he has mended his ways and wants to show young men how to mend theirs. You do this by providing “surplus generative value”—that is, giving more than you get. That’s a very good way to be, and a decent working definition of an adult. But if you’re phrasing it as “surplus generative value,” you clearly still take a transactional view of relationships.
My theory about Galloway is that he’s talking to his younger self, a guy who actually had to be told that being kind is a good idea and who needed the incentive of potentially having sex in order to give this being-a-good-person-thing a try. Fine. I guess there are some men who need to hear this.
But his evaluation of young men has a sneering quality that gives me flashbacks. When I was single, my friends and I had to stave off the stereotype that we were “desperate” or “pathetic” (well, except for the times when we were too independent or intimidating).
Galloway paints an equally unflattering portrait of young men, describing a generation of shiftless babies, living in their parents’ basements and staring at screens.
Why go through the pecking order of trying to establish friends when you have Reddit and Discord? Why put on a tie, show up, try and navigate the difficulties and complexities of the workplace when you think you can trade stocks or crypto on Robin Hood or Coinbase? And why would you go through the effort, the expense, the potential rejection, humiliation, effort, perseverance, willingness to endure rejection involved in establishing a romantic or a sexual relationship when you have synthetic, lifelike porn at home? I mean … one out of seven men are called NEETs. They’re neither in education, employment or in training. They’re literally doing nothing. And 63% of men under the age of 30 aren’t even trying to date.
Wait? Two-thirds of men under 30 aren’t even trying to date? That doesn’t sound right, but it’s a stat Galloway repeats elsewhere.
The stat is wrong, though. Just ask … Scott Galloway. When “Prof G,” as the expert marketer has branded himself, recites the finding in writing he links to his source and describes the data accurately: “63% of men aged 18-29 in America are single (neither married nor in a committed relationship).” He doesn’t say that 100% of young single men aren’t trying to date, because … that’s absurd.
As for the NEET stat, yes, globally 14% of young men are not in employment education or training. But are they “literally doing nothing”? NEETs include people who are looking for jobs or are family caregivers (which is one reason why 31% of young women are NEETs). They also include people who are unable to work due to mental and physical disabilities. When you remove young men who are not disabled, don’t live with a disabled adult, and aren’t parents living with one of their children, the number drops to 8.7 percent.
Economics writer Noah Smith offers a refreshing counterpoint to Prof G’s bleak portrait, though he doesn’t specifically reference Galloway.
Smith’s message to young single men is that their situation isn’t nearly as dire as certain influencers and sub-Reddits would have them believe, noting that while both young men and women are having less sex than previous generations did, most still are. Also, it’s not true that a small group of super handsome and wealthy guys is hoarding all the sex. To put it in Galloway’s words, we’re not in a “winner take most” environment. Smith explains:
Sexlessness rates of ~30% for young people is pretty bad news, in my opinion, but the number is pretty equal for men and women. And in any given year, most men and women are monogamous, with only a few people having large numbers of sex partners. … Yes, male sexlessness is more common than female sexlessness, but only a little bit. Yes, there are more men than women who report a large number of sex partners, but the difference is very small. A majority of young people are just having sex with exactly one other person—no more, no less.
Then he offers this dose of sanity:
Dating and sex are very achievable for a regular guy. You do not have to be 6’5”, work in finance, or have a trust fund. You just have to be a regular, normal, typical guy.
The rest of the post is dedicated to giving dating advice. Smith makes clear that he’s not a dating expert, and that this post is just a one-off from a guy who has struggled with some of this stuff himself. He agrees with the boilerplate dating advice that getting in shape and dressing well are good ideas; his tone is gentle and friendly rather than exasperated. He also advises men to focus on being good companions and attentive lovers:
Companionship means keeping a woman company—going to dinner, cuddling on the couch, talking about life, etc. But it means a lot more than that. It means helping with unexpected challenges, like health problems or finances. It means giving her advice on her job or her personal problems. It means throwing spiders out of the house when she’s too scared to grab them in a cup.
Again, if a certain subset of young men needs to hear this, fine.
Smith correctly points out that the castle wall isn’t that high and that the alligators don’t have teeth, but the framing is still that a girlfriend is a prize to be won, a safe to be unlocked. Smith advises learning about a woman’s interests and what turns her on in bed—good, good!—but there’s also a flattening way he talks about women that reminds me of how the old dating guides described men.
He neglects to mention the importance of finding a woman you … like.
Not just someone you want to sleep with, but someone you want to hang out with because you enjoy the way she thinks, because you connect with her sense of humor and her general outlook on life. A person you truly see, and who sees you.
On one of our first dates, my husband said, “I like the way your mind works.” I feel the same way about him. But here’s the thing—we’re not for everyone. We have both received the feedback that we’re “too negative.” It’s a running joke in our house. Sometimes we will go on a tear about how awful everything is and then one person will pucker their face and whine, “Why do you have to be so negative?” One person’s dark and depressing is another person’s refreshingly honest.
Yes, most of us are average—basic math dictates that. But we’re also particular.
Think of the happiest couple you know. What are they like? Are they the people with the best workout routines and the nicest clothes? The ones who have the most impressive careers and most beautiful homes? Is everyone around them blown away by their demonstrations of excellence?
Or are they two very particular goofballs who wake up every day thrilled to have found someone who laughs at their jokes and is willing to put up with their nonsense? Success in dating isn’t about being best-in-class; it’s about two weirdos finding each other.
I’m not saying it’s easy. My search for the particular goofball who would put up with my nonsense took many, many years.
And during those years, I did go to the gym. I did yoga and meditated and got good haircuts. I’m glad I did that stuff; it made my life better. But I regret the intention behind it. I regret that for many years I viewed myself as a renovation project, the success of which would be measured by my ability to secure a partner.
I found my goofball, but it could have gone another way. There is another timeline where the very arbitrary set of circumstances that led to meeting my husband didn’t happen. Maybe I would have found another weirdo who was right for me, but maybe not.
That’s why I’m so passionate about this. I know exactly how other-timeline-me would have felt. I would have told myself and told myself and told myself that it was just bad luck. But I wouldn’t have believed it.
So if you’ve found your goofball, count your blessings and don’t be snotty to the people less lucky than you are. (Though in my experience, the people who are the most smug and superior are not the ones in the best marriages.) If you haven’t found yours yet, I hope this piece is helpful.
The world is mean and unfair, but there are some pretty great goofballs out there.
Single people, what do you think? Is it as dire as Galloway and others are saying?
People in couples, how did you and your partner find your way to each other?




Thanks for interesting insights and dose of empathy for singles. I just returned from a trip where I was the only non-married member of a group of 25 female physicians. Nothing negative was said to me, and yet it was clear that everyone knew I was different. The conversation was polite, but I was conscious of being an other. Recently I read about how to plan a trip to a city where some restaurants don’t allow single reservations in order to prioritize seat tables at maximum capacity. I will survive the inconvenience of being persona non grata at such restaurants, but I am still very glad to feel understood by at least one partnered person whose way of thinking I happen to respect. Not many take the time to remember what it felt like to be single, judged or treated as a failure or prize.
Really appreciate this post, though I'd push back on one word in the headline: "just." I'd love to find my goofball, but at 45, it feels harder and farther away than ever.
I go back to a lot of the ideas from _It's Not You_ and really appreciate them. While I'm glad (some of) the critiques of single life are lessening, it's still depressing to hear "live your life! travel! build your career! buy a house!" as the "solutions" to being single. Yes, you (I) can and should do all of those things. But doing so doesn't relieve the pain of being single in a world built for couples. That is, even doing these things without the intent of being a "renovation project," continuing to live life solo can sting. I know you know that, but noting it here because sometimes the important move away from "improve yourselves" to "build your life" glosses over the pain of deep yearning which is not fixed by houses, careers, vacations, or even a community of wonderful friendships.