Dating Women: The Most Enticing Romantic Possibility Life Ever Threw Her Way

This week’s New York Magazine Sex Diary features a 35-year-old writer going out with a woman for the first time and it’s pretty adorable. It’s absurd and ridiculous at times, too, but mostly does a good job of capturing the experience of somebody who suddenly finds themselves considering a possibility they’d never before considered. Namely, the possibility of WOMEN.

I don’t mean to sound immature but at this point, I’m still in shock that I have a date with a girl?! I have zero hang-ups about gay/straight/bi sexual orientations. This isn’t about shame or anything like that at all … it’s almost the opposite. It’s like this is the most enticing romantic possibility life has ever thrown my way.

This kind of story — grown-up straight woman meets grown-up not-straight women, then suddenly considers the possibility of dating women for the first time — is a popular one in film, television and literature, but rarely do these revelations occur without a great deal of hand-wringing, retrospection and self-doubt. What does it mean? Am I gay now? Is this why I was so obsessed with Britney Spears? What will my parents think? What will my friends say? Why am I ashamed to hold her hand in public? 

But our culture is shifting, slowly but surely, at least in some circles in some parts of the country. We’re hearing more and more real-life narratives from adults in which falling for a woman in your twenties or thirties, while unexpected, isn’t shocking or confusing, either. Nor do these stories fit into the “falling in love with this one woman helped me realize I’d always been queer / bisexual / gay, NOW WHAT DO I DO” column, which is probably the column most “coming out to yourself” stories fit into, including the fictionalized ones.

If there is a column for these new narratives, it might be this: “falling in love with a woman made me realize I was capable of falling in love with a woman.” The sentence doesn’t have to end there, of course, most would also tack on an “and therefore I guess I must be queer or bisexual or gay or sexually fluid, but whatever, it’s not a big deal.” What makes these stories different than so many other queer narratives is the complete lack of internalized homophobia — for people like me, it’s stunning that any woman could be so nonchalant about suddenly finding herself playing for a different team. The idea of going on a date with a woman for the first time was hardly incidental for me, it was loaded with meaning. I spent most of my life completely certain that I was straight and completely horrified by the idea of being a lesbian, despite growing up in a very liberal area with a queer parent. In fact, my former aversion towards out-and-proud lesbians remains the only evidence I have that I’ve been queer all this time, because I don’t have the formative “crushing on my best friend” or “fantasizing about women” stories I hear from many other lesbian and bisexual women.

The Sex Diarist’s narrative is one of many we’ve heard lately remarkable not for treating the gender of one’s partner as incidental (historically exemplified through ideas like “we’re all just humans! I fall in love with a person, not a gender!”, which is true or a lot of people in the middle of the Kinsey Scale but not for everybody) but for acknowledging that yes, for most people, dating a woman is different than dating a man, but it’s not “less than,” it’s not bad, and it’s not a big deal, either. We’re entering an era when it’s possible for a woman to grow up in or live in a homo-friendly environment that enables her to consider dating a woman when the opportunity presents itself without worrying about coming out to intolerant family members, being rejected by her friends or suffering at work. Even big-name Hollywood actresses have publicly acquired girlfriends without losing work (e.g, Kristen Stewart), which would’ve been unthinkable ten years ago.

Historically, even the most open-minded liberal couldn’t consider suddenly dating a woman without some degree of strife unless they’d already cut themselves off from traditional society and expectations, like hippie communes. Musician Julia Nunes touched on this in her recent Autostraddle interview when she talked about how she was lucky enough to grow up in such an accepting environment that eventually falling for a girl for the first time wasn’t a big deal or an identity crisis.

Chloe Caldwell’s 2014 novella Womena beautiful story about the author’s first same-sex love affair, manages to address frankly how different it is to be with a woman without making sexual orientation itself the subject or the obstacle of her story. Early in the book, when she’s found herself drawn to this woman, Finn, but hasn’t yet given it a name, Caldwell writes, “I knew I found Finn’s aesthetic attractive, but I hadn’t yet explored feelings of being attracted to her, in part because I hadn’t yet explored my ability to fall for a woman. I figured if I was going to be with a woman, I would have been with one by now. I would know if I was bisexual or gay. Being a writer, I assumed I was at least mildly self-aware.” And then, of course, she falls, quickly and desperately, in love with a woman she cannot have because this woman is already in a relationship with somebody else. It’s unhealthy and destructive. But she falls, and falls, and falls, and this new categorization of affair is approached not with hand-wringing, but with nervous, tentative, flushed excitement and curiosity.

A similarly enchanting narrative begins mid-way in the new Netflix documentary Tig, when out lesbian comedian Tig Notaro becomes fast friends with Stephanie Allyne, a straight actress she worked with on the film In A World. Although Allyne and Notaro are clearly falling for each other — texting nonstop, becoming inexorably obsessed with each other’s every word and move, involving each other in their work whenever possible — Allyne resists to categorize it as “falling in love” because, of course, she’s straight! “I don’t know how to go forward in my life without this person,” Allyne recalls feeling after her and Tig had decided to take a break from their friendship because Tig’s feelings for Allyne were too strong. “I knew if I don’t say ‘yes’ to this in my life then I am not following my feelings and my heart.” I won’t spoil the film for you, but you’re probably already aware that the two are presently engaged to be married, so there’s that.

Ye olde fictional narratives never turned out quite as well as these present-day true stories do. Jessica Stein tried really hard to love her girlfriend as much as her girlfriend loved her, but ultimately she was just too straight to make it work. Samantha Jones quickly grew tired of her relationship with Maria in Sex and the City, and exited with several digs at lesbian relationships in general. In Six Feet Under, Claire’s brief experimentation with bohemian lesbian artist Edie was similarly short-lived, as Edie reminds Claire that “the world’s not your own private fucking chemistry set.”

I don’t know how we’ll categorize this type of human going forward or where this type of experience will fit in to other LGBTQ narratives — if anywhere. We’ll never know if it worked out for the Sex Diarist and her anonymous female date “Rose” — if her quickness to judge Rose for not making cookies from scratch is any indication, it probably didn’t — but rest assured they did eventually have sex and “it felt fucking incredible. Every single second of it. Fucking. Incredible.” But you probably already saw that one coming, eh?

Riese is the 38-year-old Co-Founder and CEO of as well as an award-winning writer, blogger, fictionist, copywriter, video-maker, low-key Jewish power lesbian and aspiring cyber-performance artist who grew up in Michigan, lost her mind in New York and then headed West. Her work has appeared in nine books including "The Bigger the Better The Tighter The Sweater: 21 Funny Women on Beauty, Body Image & Other Hazards Of Being Female," magazines including Marie Claire and Curve, and all over the web including Nylon, Queerty, Nerve, Bitch, Emily Books and Jezebel. She had a very popular personal blog once upon a time, and then she recapped The L Word, and then she had the idea to make this place, and now here we all are! In 2016, she was nominated for a GLAAD Award for Outstanding Digital Journalism. Follow her on twitter and instagram.

Riese has written 2843 articles for us.


  1. While I understand some of the objections to the tone of the article, I can relate to the author’s experience. As someone who discovered her attraction to women at age 30, I can say that the author’s apparent lack of angst (not to be confused with nonchalance) may have a great deal to do with age. Discovering my queerness in my vulnerable teens or even early 20’s would have been an entirely different ball game. By 30 I had moved away from my hometown, started a career and was surrounding myself with new friends of my own choosing, and that provided me certain privileges for self-discovery that my younger self just did not have. So when I fell in love with a woman for the first time, while still young but with greater perspective, I was able to see it as a gift rather than a burden.

    But I do recognize that this was a privilege. I wish the experience of coming out to oneself could be less of a burden for queers of all ages, but we have a long way to go before it is. And things were easier for me precisely because others have fought for it to be that way.

    Which is not to say it wasn’t a big deal. I worried (and still worry) about how to explain my bisexuality to friends and family, all of whom have never known me as anything but straight. But their approval is less important to my self-development as it once was.

    For me, the most disorienting part of discovering my sexuality at this age is the element of surprise. As in, “how could I have not known this about myself??? Why now? Where do I go from here?,” which admittedly are rather benign questions compared to some of the internal struggles many others face, but they are valid ones nonetheless.

    I think the author downplays the significance of the discovery because of the nature of the column (sex stories). To me it doesn’t matter that a casual encounter, and not love, is the catalyst for the author’s self-discovery. We all have had brief encounters that have marked us in some way. My fleeting relationship with a woman changed my life forever, so it hurts to think that something so profound to me could be taken less seriously because my journey to self-acceptance was a little less rocky.

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