Sex and the Single Woman: 24 Writers Reimagine Helen Gurley Brown’s Cult Classic, edited by Eliza Smith and Haley Swanson, comes out in exactly one week and is sure to make readers think about many of the topics the original version brought up when it was published in 1962. Though Gurley Brown’s messaging in her book was radical for its time, she left out so much, and so many of us. Now, in this updated anthology, our collective voices (all 24 of them!) come together to share experiences and identities that were excluded 50 years ago. At its core, the new anthology is a celebration of autonomy and an honest rendering of what it means to be single in 2022.

Because the book includes so many different queer perspectives, and because two members of Team Autostraddle (myself and Xoai Pham) have essays published in the book, we thought it would be fun to do a roundtable where you could hear even more from some of the queer writers who contributed to the book. We left the question very open-ended on purpose: we simply wanted to know what was happening behind the scenes for these writers when they worked on the essays that eventually ended up in the published anthology. They were all generous enough to share intimate details from the process with us — and if you like reading what they have to say about their essays in Sex and the Single Woman, you can pre-order your copy of the anthology so it arrives on your doorstep in exactly one week and then you can actually devour the essays themselves, too!

Kristen Arnett

I had a lot of reservations when it came to writing this essay. It was a tough one for me. Essay works always feels like a particularly strange excavation. I’m actually just trying to figure out the right way to ask myself a question. I get that one idea that won’t leave me alone, one that feels like a pebble trapped in my shoe, and then I essentially come up with dozens of ways to ask myself the same question, over and over again, with varying degrees of success. So going into this particular essay – specifically one in which I am writing about queer boundaries – was difficult, because I found that I was unpacking a lot of conflicting feelings. It became an exercise in unrelenting self-discovery; one that required me to think and rethink what I knew about myself and my own relationship to intimacy and queer relationships and consent.

Another thing that interested me in this writing process – and by “interested” I mean at turns wildly frustrated me and also surprised me – was the fact that there was no right way to approach the initial “question.” I jabbed in from a variety of angles, attempting to discover what could work as an opening, a complete center, or even a solid conclusion. What I found was that I could essentially enter this essay at any point in the narrative, which allowed me to shift all the parts of it freely. The opening became the ending, the middle became the new beginning, and so on, etc. It felt a lot like playing with puzzle pieces; those ones in the box that want to fit together, but aren’t exactly right. At first, this aggravated me – why couldn’t I nail any of it down into a concrete structure – but little by little, it began to make sense to my exasperated brain. I was trying to come up with a narrative structure for boundaries and consent when it came to experiencing my queerness – how I move through the world in a queer body, how other queer bodies interact with my own queer body – and the boundaries were therefore naturally liquid, requiring a kind of “looseness” when it came to considering its framework. I think what I eventually settled on works well, but I wonder how it will look to me in the future: how will this essay sit inside me in six month, three years, or even a decade from now? I imagine it will have shifted again. Slipping free, loosing itself from the shape I’ve pressed on it, refusing to remain rigid.

Rosemary Donahue

It is a frequent conversation among writers: when writing about the people in our lives, what — and how much — do we tell them? There’s no hard and fast rule, here, which is hard for me (I love a hard and fast rule; when I know ‘em, I can break ‘em). But I’ve come up with a few of my own that I’m comfortable with, and that have allowed me to write pieces like the one I wrote for SATSW.

The first rule is that if someone I care about greatly is going to play a major role in a piece I’m working on, I like to tell them. This is less about asking for permission than providing information, though it always does carry the slight risk they’ll object. However, with writing, there are always workarounds; changing names, for example, to provide a layer of anonymity where appropriate or desired. While it’s always a possibility that whoever you’re writing about may not love what you create or that they may remember things differently, either of those things is better than making someone feel as though you betrayed their trust. I’d rather write without the anxiety that I’ll be putting an important relationship on the line by the sheer fact of the piece.

Since the story I wrote for SATSW — a piece about my early relationship, then marriage, then divorce with my ex husband — fell squarely into this category, I talked to him shortly after I pitched it. At that point, I’d already been writing about not just our relationship but also divorce for a while, so he mostly just congratulated me. Then (though this is not always what I do; I often will just inform a person of the piece, its general thesis or theme, and tell them I’ll send it to them when it’s published), we talked about some of the things I’d be including to jog my notoriously goldfish-like memory. Being able to talk through some of the finer details of the piece — like “What did we have for dinner the first divorced Thanksgiving we spent together?” and “Wait, when did you move out to California?” — was helpful.

The second rule I’ve decided on when it comes to writing about others, however, is that the first is nullified if the person in the story has harmed you past the point of deserving such care. Your stories are always your own, but in this case, especially, I believe you have a right to do what you want with them without so much as a courtesy text. Sometimes, we move through complicated emotions through our work; it is a gift to include other people in this process, and one not everyone is worthy of receiving.

Josie Pickens

I take great pride in all of my layers. In the words of the great American poet and essayist Walt Whitman, “I contain multitudes.” I am a Black, southern, queer woman of a certain age who holds non-traditional beliefs around love, sex and relationships. And although I share my beliefs and ideas widely through my writing and public conversations, I rarely share them from a personal perspective. Writing an essay about how I’ve come to understand myself as polyamorous was a bit more complicated than I imagined it would be, and viewing those complications through a cultural and historical lens was necessary for me to free myself to not only accept my own love and relationship choices but also to share them with the world.

So many Black women find it difficult to step outside of tradition when it comes to how we partner and how we sex. For us, the legacy of slavery finds its way into our love relationships and our bedrooms. Our foremothers held no autonomy over their bodies, were not allowed to choose monogamy for themselves, and could not legally marry. Enslaved Black women were ferociously hypersexualized in order to justify the sexual violence committed against them. So, it makes sense that many of us struggle with shame around sex, sexuality, and how we choose to partner if those ways of being fall outside of what is conservative and traditional. We are afraid of the judgment we might encounter when we are honest about how certain traditional scripts simply do not fit us. Scripts that suggest that we shouldn’t focus on our own pleasure or explore what makes our bodies quiver. Scripts that say we should be satisfied with one partner, even if we feel unfulfilled and long for something more. Scripts that say that queerness is an abomination—a sin against The Divine. Yes, these kinds of judgments persist even in 2022. Yes, showing up as “other” requires a certain level of bravery that sometimes I’m unsure I possess.

What I know is that I want and deserve to show up in the world as my whole self—with all my multitudes shining brightly. I want women like me to know that it’s okay to choose the “other”, which ultimately means that it’s okay to choose ourselves.

Vanessa Friedman

My essay in Sex and the Single Woman is about friendship, love, loneliness, and fisting… so in some ways it’s exactly like every essay I ever write! I’m kidding, kind of, but not really — in the classes I teach about writing I tell my students that we all have obsessions we come back to over and over as writers, and that’s not a bad thing! These topics are ones that I am fascinated by and will likely be exploring for the rest of my life, and it feels natural that so much of my work centers platonic love and bold pleasure in the fact of sadness and growing up.

That said, it’s a little bit funny to me that this essay, which I originally wrote for a grad school workshop in 2019, examines the idea that I may simply never fall in big romantic love again (and ultimately decides that that’s okay, and is not a balm against loneliness, or maybe is not the only balm) and yet I have to admit that I have experienced big romantic love twice since initially writing the piece. I don’t think that makes it untrue, of course. Instead, it underscores something horrifying and real and hilarious and mundane about being a writer, or at least a nonfiction writer who writes about herself in the present: things are always changing. I can only know what I know now about myself. My future is unknown, and my future thoughts about life and the universe are unknown, too. I don’t see that as a problem or a flaw; I simply see it as reality.

When I think and teach about writing, I often site something Michelle Tea said to me in a workshop in 2019, just a few months after I wrote this particular piece: “Being a writer means growing up in public.” So I think of this essay as just one more step in my growth. I’m proud of it, and fucking delighted to be in an anthology with so many literary rockstars, many whose writing — their own growing up in public — helped me become the writer and dyke I am today.

Keah Brown

Honestly, the first thing that went into writing the piece was talking about it in therapy. When I was approached to write for the anthology, I was coming fresh off of the last situationship mentioned in the essay. In fact, toward the end I had mentioned to the person I was talking to that I was approached to write it and they gave me their blessing as long as I changed their name. I obviously did and I tried my best to approach the writing process from the lens of being grateful for having it and understanding that just because Something does not last  does not  mean there wasn’t anything to learn from it. I came out later in life at 28 and I was so scared that no one would ever love me or want me and at 30 I’m still a little scared but having those experiences even though they didn’t last allowed me to see that I do have value romantically and then I can be more than just a great friend to someone. I am a person who loves the idea of romantic love and wants to be romantically loved and so as I sat down to write, I decided it was important to be honest about wanting it still. One of the other things that was important while writing for me, was to tell the truth and not sugarcoat anything. I wasn’t perfect in the Situationships despite how short they were, and I learned that I need to stop being so afraid to be upset when something hurts me or something is that it will be the wrong way in the fear of losing the attention of someone. One of the most profound and truly exposing things that was said to me during one of the Situationships was that I will avoid letting myself be upset and hurt because I want to be loved so badly. And the thing is, I knew it already. And so as I began to write about these experiences, I’d use  post it notes to remind myself that  while in many ways this was a really fun thing to experience after being in the closet for so long, I also deserve to be treated well and I deserve to feel what I need to feel and say what I need to say and not make myself smaller for the betterment of other people.

So, TL;DR behind the scenes of writing my piece for the anthology was just me reminding myself that I deserve to be loved well and I deserve to figure out how to put myself first.

Samantha Allen

When I was asked to contribute to an anthology about Helen Gurley Brown’s Sex and the Single Girl, I thought first of the issues of Cosmopolitan magazine I used to read in secret, back when I was still in the closet pretending to be a heterosexual man in various doomed straight relationships. After I came out as trans, my version of womanhood ended up looking leagues apart from the quintessential Cosmo girl. These days, I live in loungewear, own two hairless cats with my gay wife, and wear makeup five times a year at most. So I wondered in hindsight why Cosmo was the text a naïve younger me had gravitated toward. Perhaps it was because I could easily slip a copy on the checkout counter conveyor belt and lie that it was “for my girlfriend.” But I also realized that, between SSG and Cosmo, Brown had helped build a world in which her particular version of womanhood — white, slender, sexy, and upwardly mobile — had become metonymic for womanhood writ large. In a certain era, being a Cosmo cover girl was so significant because it meant you were the standard women measured themselves against. You embodied the norm.

That’s how I decided to write about the period of my early twenties when I was still trying to convince myself that I could be a straight guy, before I understood that womanhood could include trans weirdos like me. Despite having written (count ’em!) one, two, three memoirs, I had mostly glossed over these experiences, in part because they felt too nuanced to explore in those more thesis-driven books, but also because I still feel deep shame over my failure to be the man those girlfriends of yesteryear wanted me to be. I’m not saying I should have lived a lie for their sake. That wouldn’t have helped anyone. But I do regret the time I wasted, words I uttered, and life I spent. I’m deeply sorry in ways that have long felt impossible to express. Reading Sex and the Single Girl in tandem with a re-read of Jack Halbertam’s The Queer Art of Failure crystallized for me that I wasn’t a categorical failure, per se, but that we have all been failed by the norms around gender, sex, and dating we have inherited. Of course there will be obfuscation and misunderstanding when we’re trying to make sense of ourselves — and each other — using broken lenses.

I don’t think that analysis absolves me of responsibility for having been a bad partner. If anything, it brings the selfishness that can’t be blamed on my dysphoria into even sharper and more painful relief. And it also helps me find a kind of melancholic queer beauty amid the hurt of those relationships. We have all been failed, and so we fail ourselves, and so we fail those around us. To err is human, and to err is queer. Anyway, what I’m trying to say is my essay is a rollicking funfest that’s not at all about processing guilt and trauma. Is it too late to try to get you excited to read it?

Xoai Pham

So much of what people see about single womanhood is based on white, wealthy narratives. The whimsical girl who, with a sudden breeze, gets blown into the arms of a man who is dashing and has the shiniest smile. I wish that was me! But the girls I know, the dolls, have very different stories. And they’re just as important and, most of the time, they’re a lot more juicy. I wanted to focus on the aspects of singlehood that force us to grow. We are told every day, sold products at stores — we even have a commercial holiday called Valentine’s — that trains us we should always avoid being single. There’s a despair in it. It’s like being single is never being able to scratch an itch in the back of your brain, something telling you you’re going to be alone, that you were never worthy of a relationship anyway. That’s a message that trans women get more than anyone else, I’d dare say. But the point is more that we all struggle with finding our value, and we search for it in other people. That journey leads to discoveries that are joyful and scary. Is there anything better than women writing about themselves?

Sex and the Single Woman: 24 Writers Reimagine Helen Gurley Brown’s Cult Classic is available for pre-order. The anthology publishes next Tuesday on May 17, 2022.

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