Until I started dating a woman a year and a half ago, when I was 33, I had only ever dated and slept with men. I was even married to one. It hadn’t occurred to me in any conscious way that I’d be interested in something else.
Then, a year after my divorce, I started working on a big project with a female co-worker—and found myself really looking forward to our meetings and having a lot of fun Slacking with her. After a few weeks of being really excited to see her at work every day (and an incident where I got super inexplicably flustered asking her if she wanted to get lunch), I thought, Huh, isn’t it weird that I think about this co-worker a lot outside of our jobs, and really just want to be talking to her? That seems… strange, doesn’t it? Before I knew what was happening, I answered my own question: Oh, this is a crush.
I had no idea what to do with this information. Part of my confusion was around what having this crush meant in terms of my identity. Realizing you have queer or bisexual feelings, particularly if you’re an adult over the age of, say, 20, can lead to getting caught in a cycle: I want to explore these feelings so I can figure out how to label myself… but I need to label myself to date/kiss/fuck a real person according to the rules of that label.
That was definitely the case for me—I was really in my head about labels like “queer” and “bi” (how dare I claim to be of a marginalized group when I had no lived experience to show for it?). I also hated the idea of using another person to “experiment.” I was worried about the possibility of it going somewhere. If we made out and I didn’t like it, I’d feel terrible… but if we made out and I did like it, I would, at some point or another, have to confess that I had never had sex with a woman before and had no idea what I was doing.
I finally broke down and told my very close friend Sally, who is gay, what was going on, and she was endlessly reassuring—she was the exact right level of thrilled; confirmed that it sounded like my crush at least wanted to make out with me; and encouraged me to not get too in my own head about labels.
Still, I had a lot of questions that I was too embarrassed to ask her (read: all the sex ones). Even when I finally broke down and typed “straight girls” into the Autostraddle search bar and read everything that came up, I couldn’t find quite what I was looking for. So that’s why, 18 months later—the amount of time my former co-worker/now girlfriend and I have been together, by the way—I’ve decided to simply be the content I wished to see in the world and write this guide to exploring relatively late-breaking queerness.
If you are a woman who is questioning the sexuality you’ve always known, or are starting to feel like it’s time to finally answer the phone that has been quietly ringing in the back of your mind for years, and have no idea where to go from here, you’ve come to the right place. With the help of a few experts and input from other queer people (plus questions from actual people who are currently curious!), I’m here to answer some of the questions you might have. (And, an aside: If you’re currently in a hetero relationship that you’re not looking to end any time soon, you might find “How to Explore Your Queerness When You Have a Straight Partner” helpful.)
So, this is something I didn’t predict! Was I always gay, and I just missed it, or is it a real thing to develop queer feelings later in life?
It’s an extremely real thing, and doesn’t invalidate all of the straight relationships you’ve had—or will have!—either. (For starters, bisexuality simply… exists!) “Coming into your queer identity later in life is completely normal and common,” said Rae McDaniel, a Chicago-based certified sex therapist who works with people who are feeling anxious about a transition they are experiencing in sex, gender, and/or relationships. “We grow up in a culture that doesn’t support exploring a queer identity in the same way it supports exploring a straight identity, [so] it’s hard to identify ‘clues’ that might point to attractions to anyone other than cisgender dudes. You know, that best friend that you cuddled with all through high school and got weird with when she got a boyfriend? Clues like that.”
Compulsory heterosexuality—that is, the idea that we’re straight until proven otherwise—has an enormous role in this, too. Most people aren’t encouraged to start thinking about attraction from a place of, What does a crush feel like to me? Do I have a crush on him? Do I have a crush on her? Girls are simply asked, “Which boy do you have a crush on?” And, if you’re bi, you might actually have bona fide crushes on boys! All of this, along with widely held stereotypes about what queer women look or act like (and what they don’t look or act like) and the predominant narratives around “intense female friendships” (definitely no homo!!) can make queerness fairly easy to miss.
McDaniel said the way society discusses sexual attraction has a lot to do with it. “Our culture doesn’t talk about or prioritize teaching folks with vulvas about what arousal and pleasure looks like for them,” they said. “Folks who were assigned female at birth might not be as tuned into how their bodies are responding to potential attractions.”
Heather Corinna, the founder and director of sex ed website Scarleteen, told VICE that assuming that people’s attractions will stay static throughout their lives is a bit like thinking that the job you wanted as a five-year-old is the same job you’ll want forever. Yes, that could happen… but, in general, it may change over time.
“It’s possible that you didn’t miss any clues and your sexuality simply evolved,” McDaniel said. “It’s true, and supported by research, that sexuality can be fluid.”
“It’s really common to come out later in life,” Lindsay King-Miller, author of Ask a Queer Chick: A Guide to Sex, Love, and Life for Girls Who Dig Girls, told VICE. But if you’re really worried about being “too old” to discover something new about your sexuality, it might be worthwhile to consider whether your belief that you’ve “outgrown” exploration is perhaps rooted in some misguided beliefs about aging and who is “allowed” to have good sex, or in the misconception that being LGBTQ is only acceptable if you do it in college.
If “Could I be gay/queer/bi?” is a question you have continued to ask yourself over time, that alone is something to pay attention to. You don’t have to take action on it; you can just… acknowledge it. Even if you’re reading this and thinking, Well, it’s a beautiful sunny day over here in Uhhhh I Guess Perhaps I’m Bi Town!!!!, you still don’t have to do anything with this information just yet.
Becoming aware of and naming your sexuality looks a little different for everyone. I can’t say what it will look like for you, but I can tell you what it might not look like: It won’t necessarily be something you “just knew” for most of your life, or that will strike you like a lightning bolt. For me, it felt more akin to a light coming on very, very gradually via a dimmer switch.
McDaniel said that if you’re feeling super stressed about possibly being queer, you should unpack that more, and consider whether you have any biases that might be influencing your thinking. “Is there some homophobia coming up for you?” they said. “Are you afraid of change? Are you nervous that you now need to buy Doc Martens, Carhartt overalls, and a truck? What other stereotypes might be coming up for you? Also, I love Carhartt overalls. You should try them.”
OK, I’ll admit that I find a lot of women hot but, like, doesn’t everyone? How can I tell if what I’m feeling is actual attraction, or if it’s just… appreciation?
As my friend Sally told me during our initial conversation, believing that every straight woman thinks lots of women are beautiful or finds lesbian porn is hot is very common among women who later realize they are queer. (This way of thinking was even immortalized in the 1999 queer-film classic But I’m a Cheerleader.)
Because of how intensely our culture objectifies women, it can be really hard to parse whether you’re feeling true attraction, or are just a straight woman who has been socialized to notice female beauty (perhaps in comparison to your own).
“Finding a person of the same gender sexy doesn’t necessarily mean you want to have sex with them,” Allison Moon, the author of Girl Sex 101 and the forthcoming casual sex guide Getting It , told VICE. “There’s so much more to sex than what’s visually appealing, and there are plenty of reasons why a person might enjoy lesbian porn besides wanting to actually fuck a woman.”
“If you wonder if you’re into ladies, consider fantasizing about the nuts and bolts of sex with a woman,” she continued. “Imagine touching her body, and touching or tasting her genitals. Imagine her smell. Imagine what she looks like on top of or beneath you. Just envisioning yourself with the specificity of actual sex can often give you good information as to whether or not you’d want ‘the real deal.’”
But there’s more to it than just sex. “When we talk about sexual orientation, we’re talking about sexual and romantic or otherwise affectionate feelings, in some combination OR about one or the other,” Corinna wrote in the lovely essay “What’s it called when a straight girl finds other women beautiful?” “A whole lot of time, trying to suss out, with absolutely no doubt, who we have sexual feelings for and romantic feelings for, to the exclusion of all other feelings, and who we don’t is very tough, and may even be an exercise in futility.”
“If you’re looking at another woman and going, Wow, I wish my hair would do that, that’s one thing,” King-Miller said. “But if you’re looking at her and going, Wow, I really want to put my mouth on her face, that’s probably, you know, something that’s worth investigating.”
I know I’m feeling something—I do want to put my mouth on her face, TBH—so I guess I should probably get on with it. So, what does it mean to “explore” or “experiment”?
“Exploring your sexuality means opening an inquiry into the workings of your own mind, and approaching your desires with curiosity and flexibility,” Moon said. “There are plenty of practical ways to embark on your own sexual exploration, including reading erotica, reading sex ed guides, watching porn, exploring fantasy, flirting, interrogating your own assumptions about yourself and other people, going to sex positive events like play parties and workshops, engaging sexually with a variety of partners, and plenty more.”
“Not all exploration of a queer identity needs to involve physical exploration,” McDaniel said. “Your sexual orientation is not just about sex.”
As VICE has reported, there’s a lot of value in connecting with other people when you’re starting to explore your sexuality: “Go to LGBTQ events, read books about sexuality or written by queer authors, support bisexual artists and musicians, or join queer groups. Online, Reddit’s r/bisexual subreddit is a funny and informative space for bi folks to ask questions or simply discuss their experiences, while the Fluid Arizona resource page and Autostraddle’s events and meet-ups can help queer folks build an IRL community.”
I highly recommend a phase of fairly “passive” exploration; follow queer comedians on Twitter, look at funny Tumblr posts about being bisexual, and peek at lesbian/bisexual meme accounts and couples accounts on Instagram. Get into lesbian TikTok. Doing this is a bit like obsessively studying an older sibling’s yearbook the summer before starting high school; knowing where you’re headed makes it easier to settle in once you get there, and consuming the fun/light stuff can help you get excited if you’re feeling intimidated. If you’re worried about being the new kid in school or not knowing any of the inside jokes, thinking of community as a virtual piece of the exploration process can really help offset those fears.
“If you’re new to a social group, there’s always going to be kind of a catching up period, and there will be a span of time when you’re trying to get to know people and establish your place and make friends,” King-Miller said. “For people who are newly out, making friends is even more important than dating.”
Also try to seek out examples of queer people who look like you—who have a similar ethnic or religious background or gender presentation. And read the stories of women who have come out as bi or queer later in life, after dating men exclusively. (There are many of us!)
OK, I think I’d like to explore dating women a little less in theory and a little more in practice. How do I start?
There are lots of options! (Of course, not all of these are going to be a good idea at this exact moment because of the pandemic, but that won’t always be the case.) If you’re already using apps like Tinder or Hinge, you could change your preferences to include women, or you could try a queer-specific app like Lex or HER. You could also go to queer bars; meet people at local events that center queer artists, authors, books, or films, or at community events like Queer Soup Night; or go to a bisexual sex party like Skirt Club.
You can also just… hit on women! Don’t be a creep, of course, but it’s totally fine to chat people up, ask them on a date, ask for their number, say, “Hey, do you want to get out of here?”, etc. in “straight” spaces as much as it is queer ones.
What if everyone thinks I’m straight and I’d like them to not think that… but I also don’t want to claim a label that maybe isn’t mine to use?
It depends to some degree on how you’re approaching dating/sex. If you’re a woman using apps to meet women, people are not going to assume you’re straight. If you’re interested in one specific person, like I was, or you’re talking to someone at a party, you might need to do a little bit more to communicate, I am flirting with you. So think about your go-to flirts, and really lean into those. Steal their hat, etc.
If you’re still concerned about people thinking you’re straight, you could let queer cultural references do some of the lifting. Wear a Shamir or Hayley Kiyoko T-shirt when you’re bopping around town; post IG stories of the queer books you’re reading with wild abandon; slap a rainbow sticker on your laptop; casually mention how you’ve been binging Feel Good in conversation… whatever feels natural to you! Trust me, queer people notice these things. Couple this with the aforementioned flirting, and you’ll be on your way.
And, again—as ever!—try not to worry too much about labels! “People think that going on a date with a woman or even expressing interest in one requires some sort of ‘official gay paperwork’,” as my girlfriend recently said to me. “Like, you currently have a regular driver’s license, but feel like, now, you need the special motorcycle license. But no one expects you to present your credentials on a date. The fact that you have set your preferences to women on an app or are on a date with a woman or are in a queer space looking to meet women is your qualification.”
“When you zoom out on the question of labels, you realize that there is an unfair expectation of non-straight people to experience… well… being not straight in some sort of physical way in order to be ‘queer enough.’ This is bullshit,” McDaniel said.
“If you want to go hook up with a woman, like… you should probably just do that,” King-Miller said. “It’s not that big of a deal, whether you call yourself gay or bisexual or queer or whatever—although I also will always make a pitch for for the label of bisexual, because it’s fantastic and it’s very welcoming, and I love it.”
Ultimately, labels aren’t as important as they might seem to you right now. “I think of labels as a way of organizing: These are the people that I identify with and this is the community that I’m part of and the people that I stand up for,” King-Miller said. “As far as actually going out and dating and hooking up with someone, I feel like labels are kind of secondary. The point of any kind of identity label is to describe the way that you feel and think and the things that you do… but having a word for all of those things is secondary to actually feeling and thinking and actually doing them.”
I don’t want to waste anyone’s time, or make her feel like she’s just an experiment, but I’m also worried no one will want to date someone who is questioning or inexperienced—any advice?
First, be honest with yourself about your intentions. If you take gender out of the equation, what are you looking for in general? Do you want a friend with benefits? Are you looking for your Partner in Crime ;)? Not only will knowing what you’re looking for make it easier to know if you’ve found it, but also allow you to act from a place of integrity.
Generally, it’s a good idea to mention at some point that you’re new to dating women, so the person you’re with can decide for themselves if they want to keep talking to you. “Lots of queer folks tend to shy away from folks who say they are exploring or experimenting with their sexuality because they’ve been burned by being an experiment in the past,” McDaniel said. “That’s super real.”
“I suggest an informed consent model,” they continued. “Before getting involved with someone while you are exploring your sexuality, let them in on where you are at in your identity development, what you are looking for, and how emotionally available you are. Let them make the informed decision about whether or not that is a relationship/sexual dynamic they are interested in.”
To be clear, you don’t have to put “BTW I’VE NEVER DONE THIS BEFORE!!!!” in your Tinder bio. Past experience and what you’re looking for tends to come up during getting-to-know-each-other dating conversations, and that’s a good time to share that you’re questioning, or that you’ve never done this before, or whatever you feel comfortable saying. If that means the other person isn’t as interested, that’s ultimately OK.
“Be honest. Be direct. Treat people as people. Some women will be up for being your first. Some won’t,” Moon said. “Hiding who you are or what you’re about to get someone into bed is manipulative and gross. If you want to figure some shit out, say so! If you’re feeling super into some chick but are worried she’ll reject you for being honest, better to say the thing and risk being rejected than getting laid based on a lie. You deserve to have your first time(s) be with people who are super into you for who you are. You may be surprised by who’s experienced and who’s not.”
“Are you having fun? Are they?” Moon continued. “Then don’t stress too much about the nuances of ideology and team membership. Just enjoy.”
Remember that all dating is an experiment. Most dates or hookups won’t “go anywhere” and no one thinks about it that much or considers it a waste of time. Don’t get so caught up in the question of “Will I like her?” that you forget that she might not like you. I say that not to stress you out even more, but to help you remember to see the other person as a human being who has their own needs and desires. Basically… don’t be this woman.
Cool; any other advice for my first forays into dating women?
Yes—try not to operate from the mindset that This One Hookup is the end-all, be-all way to answer the question of, “What’s going on with my sexuality?” I’m not a scientist per se, but I’m pretty sure that most experiments are not the kind of thing that you attempt once, under a single set of conditions, and then abandon entirely if they don’t work out as planned. That isn’t to say you should keep at it if you’re just not feeling it, but it’s very easy to feel like your entire identity is riding on your enjoyment of one first experience—which is a pretty high bar, and not the same standard we typically apply to straight dating.
You probably didn’t have one meh straight kiss or do a little less-than-thrilling hand stuff as a teen and think, Welp—I didn’t love that, so I guess I’ll never like it with any man ever for the rest of my life!!!!
Speaking of hand stuff, you might be thinking this “experiment” is mostly about sex (and we’ll get to that in a moment), but there’s actually more to consider than, Will I like fingerbanging? This process is, in part, about figuring out if you would actually want to be in a relationship with a woman.
“There always seems to be a convention that if you’re going to experiment, you need to experiment sexually first, and emotionally later,” Corinna said, “When, in fact, a better way to do that might be to be like, We’ll go on three or four dates and not have sex. See how you feel being out on the street with another woman on a date, and going to a restaurant, or hanging out with your friends.”
Try not to think of the men you’ve been with as your control group for this process. “So often, it’s a comparison,” Corinna said. “It’s like, If I’ve had these sexual feelings about men, the way I’m going to figure out my sexual feelings about everybody else is if they resemble those sexual feelings—which might be true, but also might not be true.”
It’s difficult to compare something you have zero experience with to something you have had years of experience with. And if you’re a woman strictly dating men in a culture that prioritizes male pleasure and power, it’s really hard to avoid having your desires, expectations, and behavior affected by that dynamic.
There’s no real reason to believe that the best sex you had with men was the best sex you could ever have. Use this as an opportunity to step away from compulsive heterosexuality and redefine what attraction, romance, intimacy, and “good sex” feel like to you right now. Which brings me to…
I don’t actually know how to have sex with or please a woman, and I’m worried about making a fool of myself.
I was extremely stressed about sex once I realized my co-worker crush might actually be into me, too. I knew the answers I needed might exist online, but I simply wasn’t ready to come out to Google yet. I decided to wait and then wing it, which was perfectly fine! You don’t need to have a bunch of moves memorized before your first hookup.
Your lack of experience can actually make sex better. “Being new to sex can be refreshing and invigorating,” Moon said. “Endeavor to approach sex with a beginner’s mind, even if you’ve been around the block a few times. Listen intently to your partner’s words and sounds. Pay attention to their body. Ask questions and endeavor to truly hear the answer. It’s 100 percent OK to ask for tips or guidance. Seriously, isn’t it refreshing when you’re in bed with a new person and they ask for your feedback?!”
Some questions to keep in your back pocket:
- “What are you in the mood for?”
- “What do you like?”
- “Is this OK?”
- “Does this feel good?”
- “Do you like [specific thing]?”
- This-or-that questions, e.g., “Harder or no?” or, “Faster or slower?”
- “What turns you on?”
- For after: “How did [specific thing] feel?”
Think about what you like. “Being familiar with your own body and your own fantasies, and being comfortable expressing that is much more important than knowing any particular… fingerbanging gesture, or whatever,” King-Miller said. “My biggest piece of advice for people who are worried about sexual experience is that they should masturbate.”
The thing that I wish I had remembered sooner, in my stressed-out moments, is that bodies are just… bodies. It’s easy to convince yourself that there’s some big secret when it comes to understanding the various parts of women’s bodies, which are often regarded as mysterious, complicated, and difficult to navigate—but trying new sex stuff is just trying new sex stuff! Have you tried new sex stuff before? If so, you probably know that sometimes it’s intuitive, and sometimes it’s awkward, but as long as everyone involved is a consenting adult and willing to communicate about what they want, or want to try, the awkward times are probably not going to be that big of a deal, or last very long.
Ultimately, don’t get so worried about being “bad” at something for a little while that you miss out on thrilling, fun, enriching life experiences.
I think I’m just anxious because I figured out how to make men come years ago, but I have no idea what to do to women.
This is, I think, a fairly common attitude among straight women, and it’s not great! You can’t master straight sex, generally speaking, and if you believe that you have—instead of viewing every dude you hook up with as a unique individual who likes to be touched and fucked differently—I’m sorry to say that you’re probably not actually that good at having sex with dudes.
“A lot of that feeling of ‘I don’t want to be new’ is actually ‘I don’t want to have to ask people what to do,’” Corinna said. “But everybody needs to be asking people what to do. I mean, obviously, from a consent standpoint, that’s ground zero—we have to. But from a pleasure standpoint, that’s also ground zero.”
No matter who you’re hooking up with, anyone who wants to be “good in bed” needs to be comfortable communicating during sex and asking their partners what they like and don’t like.
Also! Clits and penises are homologous—that is, they are developed from the same embryonic tissues and have a similar structure—and are truly not as different as you might think. No matter what the woman you’re into has: You’ll be fine.
What if I hypothetically want to do some studying before I’m actually getting naked with a woman?
If and when you’re ready to do some homework, there are some great resources available! (A quick note: Some of these are specifically addressed to people with vulvas, but most are applicable to women, in general.) Here are some you could start with:
- Girl Sex 101 by Allison Moon
- Ask a Queer Chick: A Guide to Sex, Love, and Life for Girls Who Dig Girls by Lindsay King-Miller
- Stevie Boebi’s Lesbian Sex 101 series on YouTube. (There’s one video called “literally how to scissor.”)
- “This Is Literally How We Do It: Lesbian Sex Positions 101” and “How To Have Lesbian Sex 102: Cunnilingus Edition” on Autostraddle. (Also check out the tags Lesbian Sex 101 and How to Have Lesbian Sex.)
- Cosmo’s “Lesbian Sex Tips for Your First Time Having Girl-on-Girl or Vulva-on-Vulva Sex” and “26 Sex Tips to Up Your Girl-on-Girl Game.” (Generally speaking, Cosmo’s UK edition is pretty helpful with regard to this kind of sex content, and it’s worth spending some time clicking around there!)
- Kinkly’s “5 Things I Wish I’d Known Before I Started Having Sex With Other Women” and “4 Safer Sex Tips for Women Who Sleep With Women.” (Also check out the Kinkly lesbian sex tag.)
- And you’re wondering about the meaning of words like top, bottom, switch, or vers, all of the posts linked here might be helpful!
I’m worried that I won’t be, you know, into it.
You might not be! That’s true of anything with regard to sex, and any new person you hook up with!
It’s also a good idea to consider whether your fears that you won’t like having sex with a woman in practice are rooted in really pervasive “ew, gross!!!” beliefs about how women’s genitals taste, smell, and feel, or the fact that you have a pretty negative view of your own genitals.
Moon said that figuring out your own sexuality “emerges from following an inner sense of rightness.”
“This usually feels like a ‘HELL YES’ moment,” Moon said. “The first time I had sex with a woman, it freaked me the fuck out. I just was not prepared for how a vulva felt and tasted. But despite my trepidation, my brain was screaming ‘HELL YES.’ So I followed where it led. When you are willing to listen to that voice (which, for many of us, can be the hardest part), you may be surprised where it leads you.”
But it’s perfectly OK if you ultimately conclude that sex with women is ultimately not for you. (By the way, if you’re ultimately not feeling it with a woman, you don’t need to let her down with a 500-word “When I began this journey exploring my sexuality, I wasn’t sure where it would go…” text. You’re not into her, and that’s all that matters. Just… be cool, guys.)
Is dating women worlds better than dating men?
I mean… women can be shitty partners, too, so dating women isn’t going to solve all of your dating problems, or be inherently easier. (It might even be harder, depending on what you’re looking for and where you live.)
Dating women isn’t, like, unilaterally awesome—but dating anyone you like and want to be with is really great, so in that sense, dating a woman is really awesome to me, and it might be for you, too,
Anything else you want me to know?
Just this: “Queerness is a gift to society that lets people realize how many erroneous assumptions we make about sex,” Moon said. “Queerness teaches us that we don’t be in love to have sex, have sex to be in love, have penetrative sex to be sexual, touch each other at all to be sexual, enjoy genital touch, be monogamous, have a gender or orientation at all, and so much more.”
“Queerness is about expansion,” she continued. “It’s about erasing delineation and requirements for what ‘counts.’ It’s about the endless exploration of joy and sex and pleasure that we are all capable of experiencing for ourselves to the degree we want.”
Realizing that people (including you!) are fluid and that the world isn’t always as it seems is a beautiful thing; it allows you to be softer, more curious, more creative—to notice love and loveliness where you perhaps didn’t see it before. I’m lucky to be queer, is what I’m saying; I hope you come to see your queerness that way, too—whatever you call it, whatever you choose to do about it, and as you have fun with whomever you meet along the way.
Rachel Wilkerson Miller is the author of The Art of Showing Up: How to Be There for Yourself and Your People. Follow her on Twitter.
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