“Ask Kai: Advice for the Apocalypse” is a column by Kai Cheng Thom to help you survive and thrive in a challenging world.
Have a question for Kai? Email firstname.lastname@example.org.
I’m a woman in my late 20s who recently came out as bisexual. I’m going on my first date with a woman and I’ve never done this before—I’m so nervous. I understand the “rules” of dating a man, but I’m not sure if it’s different when it’s two women. I feel like I’m starting all over again. Will I know what to do? To be honest, I’m not even sure how sex with women works?! (Like, I know what happens, but I don’t know how to get “into it,” or how to do things well.) How can I make this date go smoothly?
— Inexperienced Bisexual
There’s nothing quite like the rush of anticipation, terror, delight and anxiety that accompanies a first date, is there? I imagine those feelings are doubled for your first date with someone of the same gender. We always remember our firsts, whether they’re good, bad, awkward, hilarious or terrible (and sometimes—even usually—all of the above). No one really teaches us how to “do” dating, and certainly not how to do gay dating! In this, as in so much else, we queers are forced to write our own scripts, making things up as we go along.
Some very primal human fears are stirred by the experiences of dating, sex and romance: We fear rejection, of course, and the negative judgment of the people we are seeking intimacy with, because that would confirm our secret belief (we’ve all got ’em, those secret beliefs) that we are bad people, unworthy of love. Psychoanalysts believe that we also subconsciously fear that our desire is harmful to others—that we are bad people, doomed to hurt those we love.
I believe that these fears are particularly strong among LGBTQ2 folks, because we are socialized to believe that our sexuality and romantic desires are inherently wrong, aberrations to be tolerated at best and reviled at worst. Political and cultural shifts over the past decade or so have made positive or sympathetic media representations of (mostly white, middle class) queer people more common than they once were, but queer love remains stigmatized and marginalized in many places and communities. The stereotypical notion of predatory queers corrupting the innocent and ruining society still haunts us today, and I think it shows in how we experience sex, dating and relationships.
So all that to say, Inexperienced, it makes sense that you feel nervous about dating a woman for the first time—and also that you waited until your late 20s to do so. I think it’s worth mentioning that while it’s now more common for queer people to start dating in their teens, as little as 15 years ago, it was the norm for most people in our community to wait until adulthood or even later life to do so.
When I was a therapist, I worked with folks who were in their 30s, 40s, or even their 80s who had just started queer dating. And here’s some hopeful news, Inexperienced: All those people did figure it out—as much as anyone ever “figures out” dating, anyway!
I think it’s important to note that bi individuals (as well as pansexual folks, omnisexual folks and others whose sexuality doesn’t fall neatly into “gay” versus “straight” categories) face particular challenges when coming out and dating. Biphobic stereotypes tell us that bisexuality either isn’t real or is a phase, a “bridge” toward coming out as gay, and other such harmful mistruths. Notably, bisexual-identified individuals are statistically more vulnerable to mental health issues, and continue to face stigma in both heteronormative society and queer communities.
When we are teenagers, supportive adults and peers are supposed to help us navigate our fears, mistakes and awkward moments as we figure out sexuality and romance. I would argue that even privileged straight people don’t usually get a good education in this area, but queer folks are utterly failed by society in this regard. As recently as last year, the Ontario provincial government scrapped the revised sex-ed curriculum put in place in public schools in 2015, choosing instead to revert back to a curriculum last updated in 1998.
How does all this help you, Inexperienced? Well, I would suggest that the best thing you can do to help this date go smoothly is to be compassionate with yourself and make room for not knowing what to do. The so-called “rules” of heterosexuality tell us that there is a specific way that romance has to happen: The man takes the lead, woos the woman and actively initiates sex. Meanwhile, the woman follows his lead, acts coy and passively receives the invitation for sex.
To be honest, I don’t think those rules even really work for heterosexuals. One of the most beautiful and liberating things about queer dating is that beyond consent, respect and human decency, there are no rules. We get to simply ask for what it is that we want—as long as we are equally open to both “no” and “yes” as a response.
You don’t have to be the “butch” or the “femme,” you don’t have to be the “top” or the “bottom” (those are terms that mean different things to different people, in any case). You can be assertive and take the lead initiating intimacy, or you can wait for your date to do so. You can be flirty and coy, or earnest and direct. The important thing is knowing what your own needs, desires and boundaries are, and being ready to communicate about those things with your date.
This is the key to a successful dating experience: communication and honesty with yourself as well as your date. (Mutual attraction doesn’t hurt either!) When we are able to communicate honestly about what we want and what we don’t, then all the other parts of dating—like figuring out roles and compatibility—become more clear. When we understand our own needs and boundaries, we’re able to know whether a relationship is working or not.
As for sex, Inexperienced, I would say all of the above holds true as well! There’s no one right way to have sex, and queer people have sex in an infinite number of ways. My own belief is that the best way to have good sex is to talk about it with your (prospective) partner before, during and after in order to learn what works best for the both of you. This is way easier said than done because most of us simply have no idea how to talk about sex—especially when it comes to types of sex that we may have never had before.
It comes down, however, to simply taking the plunge: Ask how your partner likes things done and tell her how you like things to be done (this is assuming you have both already consented to having sex). Some examples of potential “opening” or “initiating” questions include “How do you like to be touched?” or “How do you like to get off?”
One of my favorite sex educators, Caffyn Jesse, teaches that when it comes to sexual pleasure, “relationship is more important than technique.” In other words, even if you’re only planning on having a one night stand or friends with benefits situation, creating a dynamic of mutual safety, trust and openness of exploration for the sexual encounter is more important than knowing any specific “moves.”
However, Inexperienced, if specific techniques for giving women pleasure is a big concern (or if being a sex geek is simply your thing), I am delighted to let you know that there are online resources for that: OMGYes, for example, is an educational website devoted to science-based, instructional videos that explore the ins and outs (and ins, and outs, and ins, and outs) of women’s sexual pleasure.
Once again, though, I think it’s important to note that even you if you were both a world leading expert on how women date women and a cutting-edge scientist in the field of women’s orgasms, it is still possible that this first date won’t go smoothly—at least, not in the sense that there will never be an awkward moment or disappointing experience. This, unfortunately, is the chaotic reality of what happens when human bodies and spirits collide in the strange dance we call sex and romance. I imagine that you have already discovered this, Inexperienced, in your time dating men.
I like to think that this is the whole point of the journey we’re all on—to learn that we are desirable and lovable, in spite of our flaws, our fumbling ignorance, our insecurities.
One possible, great advantage of starting to date women in your 20s is that you have your adult mind and your adult experiences to bring on the journey this time around. That maturity and wisdom will hopefully allow you to remember to be patient and kind with yourself. It will also remind you that dating is as much an exercise in being intimate with yourself as with other people.
There is a frightened, secret self hidden within all of us, Inexperienced, particularly those of us who came late to the queer dating game. That secret part of ourselves carries the pain of being young, queer, vulnerable, confused and lonely. It holds the terror that the world was right about us—that we are monstrous beings, incapable of intimacy and unworthy of desire.
Now, Inexperienced, you get to be the safe, supportive mentor that your younger self has always needed. You can hold your secret part in the security of your self-compassion, the knowledge that you are indeed worthy. You can cultivate curiosity instead of fear, openness instead of avoidance. You can tell yourself what we should have always been taught: That you are worthy of love, and capable of loving. You have always been, and always will be.