Two things I definitely hoped I’d be by 27 are financially and mentally stable. Unfortunately if unsurprisingly, I am still broke and insane.
Unlike most of the intimate and unflattering details of my personal life that I’ve chosen to bare before the internet in this column, even I find the numerical nuances of my bank account both too boring and too shameful to warrant public disclosure. But suffice it to say, I suffer from the usual economic ills of your typical un-generationally wealthy zillennial who insists on living in one of the most infamously expensive cities in the world—exorbitant student debt, inflation, pretty much everything about life under late-stage capitalism—coupled with a hedonistic streak that’s been wonderful for my career as a self-indulgent artist with enough decadently debauched experiences to fill a sex column and disastrous to my well-being on most other counts.
But in recent years, as friends my own age have begun to lap me in Big Life Events that come with Big Price Tags, it’s become increasingly hard to ignore another factor working to my financial disadvantage: I’m single. I have been for the vast majority of my adult life.
One thing you’ll rarely find the author of any “Today I married my best friend” Instagram caption willing to admit is that their relationship is likely—at least to some degree—fiscally convenient if not downright lucrative. But it’s a bit of an open secret that while society decries—and in some cases actively polices—blurring the lines between love and money (by which I, of course, mean sex and money), it remains structured in a way that financially rewards romantic partnership—particularly of the legal, governmentally recognized variety. From tax benefits to the possibility of finally clearing the wage gap by saying “I do” to a man’s salary, the allure of patriarchally sanctioned partnership is strong. Don’t worry; it’s designed that way.
And I’m not just talking about good old-fashioned gold-digging. You don’t have to be with someone who makes significantly more than you to reap the financial rewards of a relationship, whether it’s splitting expenses and sharing streaming log-ins or the simple safety net of knowing that if you get laid off tomorrow, you won’t wind up couch surfing or begging a reluctant roommate to cover your share of the rent this month. I’m aware, of course, that no two couples share finances exactly the same way (and that some—albeit, I suspect, a minority—don’t at all). But let’s put it this way: I may not be good with money, but even I didn’t need those TikTok DINKS to tell me that two incomes are better than one.
Which is one of many reasons why, for much of my mostly single adulthood, I’ve taken a perhaps inordinate degree of pride in my ability to create and maintain a life—however three-roommates-in-Queens-level humble—on my own. Not just because my hedonistic streak has a contrarian twin that delights in skirting and subverting norms but because I’d rather wake up broke than financially shackled to a man who can pull his love and my life out from under me any random Saturday afternoon if he happens to feel like it.
But lately, as I’ve watched partnered friends ascend into their late 20s, steadily upgrading from renters to homeowners, growing their joint savings, and consulting financial planners while I seem to be fiscally forever 21, it occurs to me that my romantic freedom may have been collecting interest all this time. Building a life on your own (income) is, as it turns out, a Sisyphean fucking task. Don’t worry; it’s designed that way.
Home for the holidays this past December and visiting high school friends who’ve made the cost-effective choice of staying close to home and marrying men they met in their teens, my classmates-turned-wives-and-mothers trade uneventful anecdotes about things you can do at the bank that I’ve never heard of while I debate bringing up the fact that I recently googled how to get money out of your 401k without retiring. (The answer, per the internet, is “Definitely don’t do that” and “Gambling addiction? Help is available.”)
Twenty-seven and struggling to shove my mounting debt, dwindling savings, and stagnating salary under the metaphorical mattress where I used to stuff cash men left for me on nightstands or slipped under restaurant tables, I’ve begun to wonder whether, like my indebted liberal arts degree and flashy, low-paying media career, staying single is a luxury I’ve claimed but can’t actually afford.
Sure, maybe we don’t have the advantage of saving on rent by moving in with finance fiancés who make at least four times what we do.
“But,” my roommate says when we rehash this conversation for the six or seven hundredth time, wine-drunk in the millennial-pink kitchen we’ve shared for four years while costs have skyrocketed and our salaries have inched, “at least we’re independent.”
Talking about “independence” and marriage to men as a threat to it can feel a bit reductive—a shallow, girl-powered grasp at an “I Don’t Need a Man” brand of feminism that seems dated, at best. After all, we ladies love to pretend we’re past all that, especially when it comes to the diamond rings and viral TikTok weddings we can’t seem to help ourselves from wanting. Because, come on, this isn’t the ’50s. Marriage doesn’t damn us to a life of self-medicated housewifery anymore, right? We can marry a man and still maintain our autonomy, can’t we? Haven’t you heard, yet another friend’s diamond winks from yet another engagement announcement. They changed the rules! Women really can have it all now!
But I know exactly what my roommate means: At least some man can’t topple my entire world on a whim.
Because if tying your life to a man’s can be financially fruitful, it can also be dangerous—a legal drug you can still come to depend on. Don’t we all sneeringly speculate over what happens to the stay-at-home girlfriends after the breakup? Haven’t we all seen the crash and relapse too many times to justify the high? Friends of friends who have been unceremoniously dumped by a long-term partner only to take him back within a matter of months because they’re still living in his apartment and already working two jobs and what are they supposed to do when the lease is up? Move in with roommates at 31? Start their whole lives from scratch?
And so we trade our freedom, our futures, the loves and lives we could have led or fucked up or grown from for apartments we couldn’t afford on our own and some double taps on thousands of dollars of wedding photography.
Don’t let me be misunderstood. It’s not that I have any qualms about mixing matters of men and money. It’s just that I prefer to do it without the pageantry of the marriage plot.
My senior year of college, when I returned to my sweltering Connecticut dorm room following the dramatic dissolution of the kind of whirlwind romance with an older man I suspect all delusional 21-year-old interns hope to find in New York, I knew three things. (1) I had a verified thing for older men. (2) I was in no condition to date for anything resembling romantic purposes—you shouldn’t try to run on a broken ankle and you shouldn’t try to love on a broken heart. (3) If dating men was going to be this exhausting, disheartening, and humiliating, I should be getting paid for it.
Like many college students in the 2010s, I’d made an account on Seeking early on in my undergrad career after reading an article—on this very website, no less—about that potentially high-paying extracurricular activity. While I’d toyed around with the janky interface and the often shady, photoless profiles that filled it, I’d always balked at actually taking a tumble down that sugar-coated rabbit hole. But now here I was, of legal everything-but-renting-a-car-and-running-for-president age, very single and far too heartbroken to date “for real.” Besides, I was about to graduate with six figures of student debt and big dreams of landing a notoriously competitive job in a notoriously underpaid industry in a notoriously expensive city. I figured some extra cash couldn’t hurt.
From the moment a married man in his late 40s pulled up outside my dorm in his red Jaguar while the boys’ lacrosse team gawked from practice across the way, sugar dating made me feel powerful in all the ways that regular dating had made me feel weak. After years of feeling used and bruised by men I’d loved or tried to love and coming up empty-handed, I was finally in a position to ask for what I wanted rather than just take what I could get. If youth and beauty were my armor, then sex work was my sword—my way of seizing and wielding something the world was built to weaponize against me.
An uncomfortable reality that’s easy to ignore in a supposedly evolved era in which we’re meant to believe marriage is a merging of souls, not assets is that heterosexual relationships have historically been rooted in the offer of social acceptance and/or financial stability in exchange for women’s sexual freedom. An even less comfortable truth is that sex work has always existed as a loophole through which women can leverage the power of our sexuality, something patriarchy is built on trying to quell and control—in exchange, of course, for the small penalty of ostracization, legal vulnerability, and, in too many cases, our lives.
But as a woman who was entering sex work with a decent amount of privilege on my side—including that college degree I still can’t afford in addition to whiteness, cis-ness, and straightness—I felt like I was finally getting something out of this thing I’d been taught to crave and aspire to above all else: being desirable to men. At least now I had something to show for it, proof of my sexual viability right where I could see it in cold hard cash on a bedside table in some ritzy hotel. I liked knowing that my market value as a woman—something society was going to ruthlessly quantify by my ability to conform to impossible standards of eternal youth and beauty regardless of what I did with it—was something I was actively cashing in on rather than investing in the heteropatriarchal ideals of monogamy and marriage.
Because, let’s face it, we know those investments don’t tend to pay dividends. Not for women, anyway. Sugar dating felt like the antidote, the golden ticket, the secret passageway that would lead me to a safe haven far from the two equally unattractive scripts of adult womanhood that had been offered to me: sexless spinster or silently suffering wife. Now I could cash in on my sexual value according to men, as god and patriarchy intended, without sacrificing the future versions of myself I could become if given the time and space to live outside the male gaze, to grow beyond any one man’s expectations of the way I should exist in relation to him and him alone.
By 25, however, when I found myself calculating my gains vs. losses at the end of an arrangement-turned-relationship instead of mourning it—one pair of diamond studs, a strand of Akoya pearls with matching earrings, two pairs of Louboutins, one pair of YSL heels and a large Louis Vuitton bag = not a bad haul in exchange for a year of the youth I’d been conditioned to believe was all too precious and all too fleeting—I began to suspect the heart I’d put on ice at 21 hadn’t healed quite right. I feared it had become overgrown with too much scar tissue. When I breathed deep, I couldn’t seem to feel the bottom of my soul.
You could argue that the sugar babies I read about in the mid-2010s and became at the end of that decade aren’t so very different from the TikTok tradwives of today. What are either of us if not reactions to the white feminist girlbossery of the millennial heyday, which pummeled women with the promise-cum-threat that we definitely can (read: should) have (do) it all—marriage, motherhood, careers—with little to no support from men because who needs ’em (because we know they’re not going to do much of anything). Sugar babies and tradwives represent two extremes of reactionary women under patriarchy: a madonna-whore (or perhaps whore-madonna) binary whereby one of us tries to exploit the traditional values of man-pleasing womanhood while the other cleaves to them for dramatic effect. But either way, we’re both cashing in, aren’t we?
If there were ever a time I thought that spectrum would never bend into a circle, those ends met and blurred when I was 24, the day my sugar-dating arrangement with a 50-year-old man turned into a “relationship” when he stopped paying me and started referring to himself as my “boyfriend” and I was too green or too love-bombed to negotiate. This unsolicited, unpaid “promotion” from sugar baby to girlfriend was a downgrade from the untethered cashflow I’d become accustomed to, sure. But I figured this was my chance to play the long game, to safely graduate from a lifestyle I was convinced I’d soon age out of.
As far as I could tell from the paid glimpses inside other people’s marriages I’d gleaned from husbands in hotel rooms, you could either get cheated on by a rich man or a poor man. I heard and felt firsthand the disregard men had for the wives they’d wed and ex-wives they’d divorced alike, their inability to see the women in their lives as people at all.
Surrounded by weekly bouquets of yellow roses bearing cards that promised, “You’re the one” when I’d only ever been the other one, I decided I’d take the rich man while I could get him.
A year after my arrangement-turned-sham-relationship ended the way most heterosexual unions will if you raise the curtains enough to let a man get spooked by his own shadow, I found myself wearing less makeup and blowing off press previews at pricey Manhattan rooftops to eat leftover pizza in a beautiful boy’s bare-bones Brighton Beach apartment. My 23-year-old self would have laughed in my 26-year-old face. You’re fucking a 34-year-old who lives in the hinterlands of Brooklyn? For free? You know this only ends one way, right?
I do and it did. But after all the roses and reservations, the bouquets and bullshit, the way this man plugged my phone in for me when I wasn’t looking wasn’t just enough; it was everything. And for the first time in a long time, I felt like I was breathing from my heart again.
When it ended the way 23-year-old me could’ve so easily predicted but I’d so blissfully deluded myself out of expecting, I wept over a stuffed Spongebob he’d won for me on the Atlantic City boardwalk like a 26-year-old teenage girl. And yet, crying over the ziploc bag of pretzels he’d once slipped into my unsuspecting hands before driving me to the Amtrak, I was only as heartbroken as I was relieved to have struck a nerve I thought I’d outgrown or outearned or buried so deep no one would ever find it.
I don’t mean to suggest that sex work makes you hard or cold. Just that it eventually occurred to me that it had become a shield as much as a sword, yet another defense mechanism I’d hidden behind in an attempt to inoculate myself against the kind of heartbreak that was always going to catch up to me anyway. I may very well return to some form of sex work at some point in the future—either out of admittedly increasing financial necessity or renewed desire.
But—as I recently told a man I love in one of the many hotel rooms where we do sugar daddy things but instead of collecting cash on the nightstand, I fall asleep in his arms feeling safe and seen for what may be the first time in my life—I don’t know if I could return to that temptingly lucrative side hustle without rebuilding walls I’ve come to feel more trapped than protected by. They may have crumbled around me disastrously, but only because they needed to come down one way or another. The foundation was rotten and I’d fallen straight through it. But I’d finally landed back at the warm, raw bottom of my soul.
Before ‘Sex at 27,‘ There Was ‘Sex at 26.’ Catch Up Here
The Real Reason I Date Men Old Enough to Be My Dad
What I Learned From F*cking (a Lot of) Married Men
I Used to Want to Be Hot So Men Would Like Me. Now I Just Want to Be So Hot, They Can’t Hurt Me
