Should I Try Dating Women?

I don't seem to be the only hetero-leaning woman asking this question

I’ve always been into men. Well, not always — before men, I was into boys, starting with the one who sat next to me in my second-grade Spanish class. He had black-framed glasses and wavy hair. I spent much of class acting as bored as possible, trying to impress him with my cool indifference.

In my later elementary years, it was Joey from New Kids On The Block who became the object of my infatuation. My father once caught me kissing him — or more accurately, the poster of him that I had ripped out from Seventeen and taped above my bed.

It would be years before I actually experienced a real kiss, but during those years, a lot of pining transpired. I loved the feel of boys’ shoulders under my sweaty palms during middle school dances. I loved their creaky voices. I loved their haphazard handwriting and the way their jeans hung on their narrow hips.

In high school, most of my female friends didn’t seem quite as taken by boys as I was. Then during college these same friends came out as lesbian, and a lot of things in retrospect made a lot more sense. I had a distinct sense they were disappointed in me for not joining the big coming out party, but for better or for worse, I still felt attracted to males.

I’m starting to wonder if it was for the worse.

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When my high school friends said things like that they didn’t believe that heterosexual relationships could be equal, I was initially indignant. I thought they were mocking heterosexuality and in turn, mocking me for my unoriginality — because really, what was more unoriginal than a young woman swooning over a man?

But now, with 20 years of marriage under my belt and a divorce underway, I concede their point. Not because all men are bent on domination but because our entrenched ideas about gender roles make the pursuit of equity all the more challenging in heterosexual relationships. Even if both partners are committed to upending traditional gender roles, which is an enormous if, there is so much we’ve already internalized, so many default patterns of behavior.

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It’s true that these gendered patterns of behavior can also plague same-sex relationships, particularly when children are involved. I know my share of same-sex couples in which one partner assumes the role of primary caregiver (i.e. the “female” role) and the other the role of primary income provider (i.e. the “male” role), and they sometimes grapple with some of the same thorny challenges when it comes to the division of labor.

But on average, same-sex couples enjoy substantially more egalitarian relationships, as they are more likely to take their preferences, strengths, and standards into account from the get-go, rather than default to socialized behaviors.

As a soon-to-be-single 44-year-old mother who may or may not be entering the dating fray at some point in the near or far future and who is sick and fucking tired of fighting for equity both inside and outside my home, this sounds pretty good to me.

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I want to tread carefully here. I know from more than one gay friend that it is annoying, at best, and downright insulting, at worst, for straight women to make offhand comments about how they wish they were gay. Such comments are dismissive of the very real systemic oppression that the LGBTQ+ community faces, not to mention the ostracism and abuse that so many have had to contend with in their personal circles of family, neighbors, and friends.

I’m also painfully aware that the premise of this entire story could very well elicit eye rolls from some LGBTQ+ folks, who are all too familiar with the straight female divorcee cliché—the one dabbling her toes in LGBTQ+ waters just for “fun.”

So, just to be clear, I am not saying: “Ugh, men are so annoying, I wish I were gay!”

I am saying: “I’m not entirely sure I can stomach the thought of once again making myself emotionally and physically vulnerable to a man who purports to respect women but who is blind to the many ways he benefits from male privilege, who is not actually committed to the real work of deconstructing his patriarchal conditioning, and who, if even on a subconscious level, believes that my time and labor are less valuable than his.”

I am not saying: “Dating women seems like it would be a blast!”

I am saying: “I’m aware that there would be very real trade-offs and that dating anyone is inevitably fraught with frustrations and complications. But why limit myself to a binary patriarchal paradigm when the pickings on the hetero side are so slim?”

It’s been over 20 years since I’ve hit the dating scene — and to give you a sense of how long ago that was, I was vaguely considering creating a Yahoo! dating profile at the time. Then I met the man I ended up marrying (IRL!) and breathed a sigh of relief that I’d never have to date again.

Dating was not much fun back then, and it seems measurably much less fun now. Not to mention a lot more work. I’ve heard horror stories about online dating for as long as online dating has been a thing. The litany of complaints seems to center around how many messages there are to respond to, how often people get ghosted, and how rarely people live up to their profiles.

Single hetero women share all these challenges, and layered on top of them are heaping dollops of objectification and misogyny. Author Nancy Jo Sales put it best in her opinion piece in The Guardian:

No, dating apps didn’t invent misogyny or womanizers. But they did give straight men — unvetted men — unfettered access to women… you don’t have to have a PhD to see that dating apps privilege the male gaze and give straight men an outsized idea of their power in their dealings with women.

Like most women, I’ve dealt with my share of abuse from men online. It’s a twisted rite of passage, in fact, for feminist writers to get yelled at by men. It means we’re “making it.” We know we’ve broken out of our bubble and are reaching a wider audience when we provoke male ire.

Just as there are wonderfully curious and humble men on Substack who appreciate my perspective, I’m quite sure there are wonderfully curious and humble men on dating apps. But trying to find those men? Oof.

Even if I did find the energy to wade through the egotistical profiles, vile texts, and thoughtless remarks… even if I did manage to meet a modern-day Prince Charming, who in fact wasn’t charming but authentic and vulnerable and inquisitive… even if I was emotionally and physically attracted to him… even if the attraction was mutual… even then, I would still find myself in a relationship, whether casual or serious or somewhere in-between, with someone who has been socialized in very different ways, who is not always attuned to the same power dynamics, and who likely does not fully grasp the extent to which his maleness has benefitted him — and benefits him still.

I’m quite sure dating women would entail its own pitfalls and emotional roller coasters because dating is an inherently frustrating, uncertain, and anxiety-provoking experience. But at the same time, the thought of putting my middle-aged face and profile out there on display for other women does not cause my stomach to churn.

I’ve already spent 20 years battling male entitlement and misogyny in my own home. I’ve battled it in classrooms and in the workplace. And in sharing stories about my experiences online, I’ve essentially given male chauvinists and misogynists the ability to offer me their unsolicited opinions whenever they please, which frequently include explaining to me how logic and capitalism work.

Why in the world would I, of my own volition, invite these chauvinists and misogynists into my DMs?

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Sexuality as a sliding scale is not a new idea for me — I even penned a controversial opinion column about this very topic in my college newspaper back in 2000. Still, I imagine it might be a challenging and somewhat intimidating undertaking to seek out women to whom I’m physically and emotionally attracted. I have none of the confidence of the small-waisted, smoky-eyed, long-haired women in contemporary shows and movies who so casually move between male partners and other small-waisted, smoky-eyed, long-haired women. (Yes, even patriarchy-defying portrayals of female sexual fluidity are still curated for the hetero male gaze.)

But I can’t imagine that the journey would be any more challenging than seeking out men to whom I’m emotionally and physically attracted, who also believe that I’m capable of logic and that I have some original ideas to offer about the fallacies of capitalism.

This is not about eschewing men altogether — there are a lot of men out there whom I still love and appreciate. I have a father who has made emotional connection a tenet of his life’s work (see this PBS documentary about him), and I recently wrote this tribute to my male coworkers, all of whom are actively challenging toxic gender norms. My last story, What Distinguishes the Men Who Get It From the Men Who Don’t, highlights men on Substack and other platforms who are committed to this difficult and ongoing work.

For now, I’m working on strengthening the concentric circles of community (family, friends, neighbors, acquaintances) that will endure through and beyond any emotional roller coasters of romantic intimacy my future may hold — and these circles absolutely include men.

It’s just that if and when I feel ready to pursue romantic intimacy, I intend to do it on my own terms. I don’t know yet what those terms will look like. All I know is they will looking nothing like the terms society dictated for me over 20 years ago — and wouldn’t mind dictating for me still.