On Feminism and the Hopeless Romantic

An Evolving Situation

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It is a fascinating time for romance. In literature, in the culture, and in life.

This is a book-length subject. For me, it is an everything kind of subject and informs—fuels?—nearly every part of my life and perspective, not just relationships.

Even in the workplace, for example, in the context of garden-variety executive management, data analysis, marketing… I found myself saying to colleagues, We see this differently because I am a romantic, and you are a classicist / stoic / rationalist.

(And yes, I expect a series of essays on romance will appear here at The New Old School. Though not, I promise, in succession. After my spontaneous 3-parter about serial fiction and social media, I think we’re all ready for some biweekly variety.)

What is endlessly interesting is the slew of contradictions we live with, perpetuate, and can’t seem to untangle—or don’t want to—as romantics and anti-romantics. My observation is that many who lean anti-romantic (adjective) are really anti-romantic romantics. An actual anti-romantic (noun)—through and through, in both theory and practice—is a rare species.

Women are particularly tangled. Not moreso than other genders; but specifically, intricately, and, you might say, hopelessly.

I am a hopeless romantic. Why do we say this? What is so hopeless about being a romantic? What exactly is a romantic for that matter?

Whatever it is, in light of where we are in social history, it’s old school to be one—hopeless or not.

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Last week I chatted with a young woman—mid 30s—who told me the story of her recent engagement to her male partner. She’d decided she wanted to propose. She called their favorite restaurant—one of those NYC spots where there are no available reservations ever. Sorry, they initially said; no can do. Determined, she then explained to the manager, a woman, her intentions; and the manager immediately said, “You got it, whenever, name the date, we’ll make room.” The manager said she’d never had a request from a woman who wanted to propose to a man. Absolutely she would help make it happen.

Intrigued by the nontraditional vibe of this young couple, I wanted to know more about how it went down. She’d chosen their favorite restaurant and crafted the evening as a perfect surprise. Did she follow other parts of the conventional romantic script? Was there, for example, a down-on-one knee ring presentation? Oh no, she said. Obviously I didn’t get a ring.

Obviously?

Part 2 of this story took a turn I did not expect nor fully comprehend: The young woman had been browsing engagement rings. For herself. She found one she loved. After the engagement at the restaurant (he said yes!), she informed her fiancé of the ring choice—all but declaring that a second engagement was expected. Soon after, he suggested a supposedly casual outing to their favorite museum. There, he led her to the room where her favorite painting hung. Suddenly, the room cleared for just the two of them.

A knee was taken, the ring produced, the déjà affianced popped the question (for good measure? for performance? both? I forgot to ask if she said yes, or felt the need to), whereupon a woman hovering outside the gallery entered and dramatically pulled back a hat-and-sunglass disguise to reveal herself—the bride-to-be’s best friend, who is also a photographer. Surprise! All were buoyantly amazed and joyous; professional photographs were taken.

Maybe this is not as perplexing for you, reader, as it is for me: Why the second proposal? Why the proverbial ring, and why gendered? And most of all, why obviously?

Is it because without Part 2, the engagement story is not properly romantic?

See what I mean about tangles and contradictions?¹

Image from picnic-perfect.com

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In my running list of New Old School topics, two things bumped this one up for me:

1. The numbers: Recently, over at A Reading Life, Petya Grady wrote candidly about the pressure modern brainy women feel to turn their noses up at the romance genre (detailing her own admittedly knee-jerk objections: too fluffy and feel-good, too predictable; flat and conventional writing). At the same time, Grady notes, romance is the fastest-growing genre according to industry sales figures. It’s a double whammy: More people are reading romance, and romance readers are reading more.

   

   Kiss & Tale Bookstore, NJ

   Additionally, in an article at Publishers Weekly, Bookshop.org reported 2025 revenue from romance titles of close to $70 million, a 55% increase over 2024. “Romance… has become a top-three sales category nearly every month—a significant shift from 2020 and 2021, when it barely registered,” noted bookshop.org founder Andy Hunter. And over at indie-focused Shelf Awareness, we learn that in 2025 “romance bookstores are the single-largest category of our new bookstore stories.” Bestselling romance author Sarina Bowen keeps a list of romance-specific bookstores—over 100 and counting—and annual Bookstore Romance Day, now in its eighth year, expects over 600 bookstores to participate this August.

2. I read Regina Black’s August Lane, a novel categorized and marketed squarely in the romance genre, and—in the midst of a reading rut—I found it smart and absorbing, and one of the best-written new novels I’ve read in a while. Black has become a kind of crossover ambassador for the genre (fitting, as it’s about crossover Black country musicians), here on Substack and in the industry, as a speaker and teacher. Her ideas about romance and romance writing are as thoughtful as her fiction.

There is a third reason—personal—that I will divulge momentarily. You’ll forgive me for burying the lede—a romantic’s penchant for dramatic effect.

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The romanticism of which I speak is not mere remnant adolescence or sublimated nightlight escapism. It’s not just sex or chivalry or declarations of forbidden love in the pouring rain. We’re talking about desire, spiritual heights, bodies, ambition, creative motivations, our relationships with community and family, womanhood, personhood, and the whole existential pursuit of a rich and meaningful life. Romance, romantic, romanticism—these are big-tent words, inextricable from one another.

How we feel about our own lived romances and romanticism reflects and refracts in how we feel about romance novels, romantic TV and movie dramas (new and classic), and rom-coms. Novelist and screenwriter Sharbari Ahmed illuminates this complex, fluid, and very personal interconnection over at Underdog Energy—so well that I will quote her at length. Writing about her former marriage at a young age and lessons learned, she shares:

I paid for what I now realize to be a terribly misleading, misguided, and deceptive notion of romantic love—one mostly influenced by Hollywood and smarmy songs.

I find myself unable to watch traditional romantic comedies now—my eyes roll to the back of my head—but I still enjoy a good love story. I still watch Bridgerton (though I fast-forwarded through some scenes this season and was not fully engaged), and I can’t wait for The Other Bennet Sister to stream in the US. Maybe it’s just Regency-era, Austen-adjacent love stories that I can stomach.

Also, The Other Bennet Sister is about Mary Bennet from Pride and Prejudice, who doesn’t seem remotely focused on finding a romantic partner. Maybe that’s why it appeals to me.

I will still watch When Harry Met Sally when it comes on, but that’s because of Nora Ephron’s brilliant writing, the dialogue, and the nostalgia of it. And the original romantic comedies of the 30s and 40s are unparalleled in their inventiveness and style. Movies like The Lady Eve or Bringing Up Baby. You know, back when there were real movie stars and not just Marvel action figures gracing the screen. Bridget Jones’s Diary I also exclude from this anti RC rant…I loved the titular character’s messiness and struggles with the vagaries of life.

Laurie Davidson and Ella Bruccoleri in The Other Bennett Sister

We all have our own lists and refusals and passionately defended exceptions; and these, I contend—as much as we might analyze them critically and aesthetically— are less rationally based than they are veiled maps of our most personal and imprinted romantic experiences, desires, and fears. There is no universal defense for why I can (and will) watch Jerry Maguire or any Bogey & Bacall movie over and over and over again.

And so romance fare is not “just escapism” or “my guilty pleasure,” as smart women will sometimes deflect, either defiantly or sheepishly. To my mind, it’s serious business.

In the above-mentioned “Resisting Romance,” Grady bravely resolved to stop deflecting—talking herself through her own resistance to the genre; and then, effectively talking herself out of it. In her thorough self-inventorying, we recognize the many shoulds and shouldnts around romance—in our reading piles and by extension in our lives.

Grady: I keep reading all these super intense books that just wreck me. I’ve been wondering if I should maybe try to read romance novels or something lighter like that so that I can feel more…

Husband: You mean… like a normal person?

Should we or shouldn’t we make room for romance—defined narrowly in the case of romance novels as the desire for a familiarly-scripted path to happily ever after with a soul mate—in our art and our lives? Grady starts with No, we shouldn’t, that’s corny and an affront to good art. But then she lands on a kind of sidestep: It’s not quite that we should center the happily-ever-after formula or desire; but, we shouldn’t NOT allow for it out of deference to a certain brand of feministic intellectualism that corners us into sophisticated miserablism.

as the romance novelist Jenny Cruisey puts it, “[m]odernism has convinced us that suffering and losing is more valuable than suffering and winning… So maybe what I’m resisting isn’t predictability. Maybe it’s the idea that happiness could be… allowed?!

It bears repeating plainly how crazy are the contradictory expectations around romance for women. Brainy women are not supposed to spend their best energy on romance. Self-reliance, self-love, mind over heart, sisterhood—these are today’s feminist priorities. And yet, pity or deride the woman who has thus “failed” at romance—brava on the career, but lo, she has become salty and emotionally desiccated. Some of these judgments come from men; but largely from other women. At the same time these stances are in wild flux, culturally and generationally (the dynamics of which are also fascinating).

The can’t-win conundrum reminds me of every other rock and hard place between which women have always been crammed: Don’t focus too much on your appearance; but be beautiful and alluring (on social media, at least). Be thin; but make sure to virtue-signal body positivity. Be assertive and unapologetic; but always be demonstrating empathy (emojis, explanation points). Be a great mother; but not too great, that’s creepy.

These messages aren’t even particularly subtle or implied. They’re all just sort of out there, duking it out in a nonsensical, impossible free-for-all.

Why does any of this matter? Because a clear and solid self is a human who can live a good life and do the greatest good unto others. We are affected, the best of us, by cultural and interpersonal messaging. It’s hard—harder than perhaps we care to admit—to sift your truthful hopes, desires, and values from what you see and hear around you. It’s even harder to act on these truths if they are out of sync with what you see and hear around you.

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I have always been a romantic.² Hopeless? Perhaps.

The first time I fell in love—roller coaster heartbreak #1—I was an over-serious 13 year old. It was a mammoth floodgate, surely a forever love (three whole years—which is like dog years for a tween), and beautifully mutual; until it wasn’t. The second time, I was 18. Another roller coaster, another three years, another heartbreak, this time involving a close girlfriend, to whom #2 is still married (yeah, ouch). In both cases, I will admit I never got over the pendulum swing of extreme infatuation and extreme rejection. Both periodically haunt me in restless dreams, reminding me that the malignance of unlovability—for a romantic—burrows deep in the soul.

I married young, in my early 20s—a house, a dog, a more modest and respectful affection—then we broke each other’s (and our families’ and friends’) hearts, 10 years later when we divorced, with a modest and respectful degree of ado. By my 30s, you’d think I would have learned… something. But the next romance, with a man two decades my senior, started rocky and rolled high and low, again; for 14 years. Hopeless? Not quite, not yet. Those were also the intense art-making years, with creative energy, adventurous travel, and meaningful domesticity holding us together for some time; until the rockiness came home to roost, and the relationship’s heart grew dark and sickly. The end was adult-ugly, with threats and lawyers and the like.

By then I was pushing my late 40s, and decidedly done. No more romance for me.

I was ragged and raw, but still had an intact self. I had plunged headlong into the ecstasies, comforts, messiness, and pain of adult romantic intimacy and commitment (twice) for exactly half the time I’d been alive. I carried wounds but no regrets.³ My sisterhood was solid, my creative and professional life still evolving. I had always paid my bills. I had my health. I reveled in swaths of solitude and was productive in it.

My feminism, such as it was, emerged with a clear vision statement vis-a-vis romance: You can live a very rich life with, and without, an intimate partner. Each path is beautiful and painful in its own way. It’s your choice—either way, there will be joys and consequences to bear.

Colette and her cats

I was grateful to have lived couplehood. Got it. I was ready to choose singleness, with a sense of relief and peace. I even romanticized it—the “vintage” single female writer, with her trail of relationship wreckage, like Colette or Isak Dinesen or Muriel Spark. Maybe I would become a promiscuous cougar.

Then came the pandemic.

You can’t prepare for or imagine that degree of aloneness. There’s solitude, and there’s isolation. I don’t have to tell you this. It was January 6, 2021—nine months deep into lockdown and social distancing, with no end in sight. I was living alone. On TV I watched the infamous Capitol insurrection unfold, mouth agape. I shouted out loud to no one, “What the fuck is going on?!” I thought, I’m losing my grip on reality. I thought, This is not productive solitude. I thought, I need to make some fresh ‘normal’ human contact. Two days later I did what I never, ever, ever thought I’d do: I joined an online dating site.

I wasn’t looking for romance (or sex) per se. It was an indescribable time. I was on the phone with friends for hours every week, narrating ad nauseum my day-to-day and stalled inner state. I was looking for something like erotic human energy in some general sense.

P. and I started chatting on January 10.

Four months ago, we celebrated our five-year anniversary at a cozy Chinese restaurant on the Lower East Side, laughing over the screenshots we both took and saved from that first online chat.

As of two weeks ago (cue crescendo of the strings section), we are engaged.

Reader, there was a ring, a loving man on one knee, waves crashing on a beach under cerulean skies, total surprise, and tears.

What the fuck is going on indeed. Tangles and contradictions, that’s what. Colette/Dinesen/Spark are surely wagging their fingers from the grave.

I’m looking forward to telling our story—the beginning part, which I can now look back on as we embark on the middle part—in future posts on romance and other New Old School topics. It’s a good story, hopeful and hopeless by turns, not particularly neat or conventional—whose story truly is?—despite the beach scene. There are multiverse, meta, bizarro layers of irony and mystery in that scene, for both of us. And happiness too! New old school happiness is allowed.

You will meet P. at some point. Probably. A main thing that drew us and has kept us together is our yen for many things old school. Originally, in fact, The New Old School was going to be a podcast—wherein P. and I shoot the shit, from our often diverging vantage points, about old school stuff (shooting the shit, as exemplified in those chat screenshots, is another thing that drew and keeps us together).

The podcast element may still happen. TBD. As in all things—as in romance—it’s an evolving situation.

1. Further: the young woman confessed later to her fiancé (and to me as she told the story) that in fact the young man has not the best poker face, and that the jig was up from the time the museum trip was suggested. So on top of the part 2 proposal itself, the surprise response was too a performance.

2. In subsequent posts on this subject, I will define much more specifically what I mean by this word, little “r” and Big “R”, and how I got there.

3. One always regrets hurting people you care about. But would I have erased the relationship altogether in order to avoid causing pain? No, I would not have.