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Ask Kai: Advice for the Apocalypse
13 min

I’m a young lesbian who wants to play the field. Does that make me a fuckboi?

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Dear Kai,

I am a mid-20s lesbian who got into the dating scene a few years ago through apps at a time when I just wanted to explore my sexuality. I had no issue getting into bed with new people, or seeing several people at once. When I was the one getting faded after a hookup, it didn’t bother me much—I thought everyone else felt the same.

Then I got together with a woman who told me I was leading people on and making them feel disposable. As I accumulated more (straight) female friends through work, I heard more and more stories of guys who acted exactly like I did in my naïveté, who they all hate to the bone.

Now I’m paralyzed by fear of hurting people. My girl friends seem to see even low-stakes field-playing—like texting or flirting with two girls in close succession—as unforgivable. But the line between queer friendship and queer “meet cute” feels especially blurred, and I run into a lot of “Is this a date? Are we flirting?” confusion with new people.

At the same time, it takes me several months to feel really sure that I’m compatible with somebody, that I’m ready to be their person. It feels like I have to pause making new queer friends if it even seems slightly possible that I’m entering romantic territory with someone else, which I know is extreme. 

The idea of asking my current friends where the line is makes me feel like a sadistic alien seeking forgiveness for my bad behaviour and brings up a lot of shame about being socially clueless. I thought you might have some wise words to help me find the right balance.


Am I a Lesbian Fuckboi?

Dear AILF,

Almost ten years ago, when I was a counsellor-in-training at a clinic in Montreal, my psychiatrist supervisor told me that there is a “psychotic phase of love.” That’s the aspect of love and infatuation that alters our perceptions and emotions so thoroughly that we seem totally illogical to others, and sometimes even to ourselves. Now, the “psychotic phase of love” is not an actual medical term (though my supervisor pronounced it very confidently at the time), but the phrase has stuck with me ever since—and it has often helped me to navigate the byzantine and terrifying quest to find romantic reflection in another.

The dominant culture—and yes, even queer culture—shapes us to believe that as adults, we ought to be more or less rational creatures. Pop psychology and the “wellness” industry have further instructed us that we should be emotionally mature. We are now inundated with self-help terminology about our “love languages,” about good communication, about how to “neurosculpt” ourselves into optimized, maximum-value people.

Have you noticed though, AILF, that there is something that happens to us when we are in situations that are potentially romantic or intimate? Suddenly, we lose our capacity to communicate what we want, to accurately assess and respond to the needs of others, to accept people for where they are at instead of where we want them to be.

This mysterious something, I believe, lies at the heart of your problems, AILF—and perhaps it’s why you feel like a “sadistic alien” who is “socially clueless.” Your letter clearly indicates a strong and overwhelming desire not to hurt others, but somehow you’ve missed out on the key social lessons that would have taught you how to gracefully intuit when people have started to fall for you, and then graciously navigate their unreciprocated feelings while also maintaining a strong friendship. AILF, I have simultaneously good and bad news about this: So has basically everyone else.

People regress to emotionally driven, often fearful or even childlike states in matters of love and sexuality. Our fundamental worries that we are unworthy of love and incapable of loving are triggered and surge up within us, bringing up old memories and defensive patterns that we may or may not be aware of. The spectre of abandonment is particularly powerful for some people, which is why even new relationships (or relationships that haven’t yet properly begun) can bring up deep pain in the face of perceived rejection—such as being “ghosted” or “faded” by a hook-up partner. Equally powerful is the spectre of shame, which tells us that we are not allowed to disappoint others—for example, by telling them up front that we are no longer interested, or only interested for the moment and not in the long term.

Yet what makes things even more confusing is that we don’t all manage our relationship anxieties in the same way. What makes complete sense for me might seem totally nonsensical, callous or cruel to my partners or people crushing on me. Let’s say that I (hypothetically!) choose to end an unsatisfying friendship-with-benefits by wordlessly drifting out of contact, while my former FWB starts desperately seeking “closure.” I might think, “Why are they acting so intense? We both knew we weren’t in a relationship!” While the FWB thinks, “How can she be so cold and self-centred? Does she not even respect me enough to say goodbye?”

Adult attachment theory can help us to make sense of all this. In psychology, “attachment” refers to the ways in which we experience and respond to intimacy. Our “adult attachment style” is formed by our childhood environment and socialization. An avoidant attachment style tends toward independence and self-sufficiency—which can look like aloofness, a lack of care, and/or avoiding conflict—in order to avoid the pain of rejection. An anxious attachment style, on the other hand, tends toward closeness and seeking reassurance in order to avoid the pain of being alone, which can look like neediness, rushing into intimacy and being controlling. The avoidant person struggles to feel safe in relationships that are moving too fast or too deep, while the anxious person struggles to feel safe in relationships that are ambivalent (that “do they like me or not?” feeling) or unpredictable.

The much-prized secure attachment style is supposedly well balanced between the two—though, in truth, it’s likely that all of us drift in and out of anxious, avoidant and secure attachment styles depending on the context and the particular relationship. And it’s important to remember that each attachment style has its strengths as well as weaknesses! (There are other less common attachment styles, but for the purposes of this article, let’s stick with the three described here.)

In case this wasn’t clear already, AILF, I suspect that you are getting tangled up in some attachment style conflicts. While I certainly don’t know you well enough to make any definitive statements, the fact that you don’t mind being faded out and take a long time to feel sure about dating someone sounds to me like you might fit more into the avoidant category when it comes to sex and dating. And this means that you might struggle to anticipate and respond to the needs of partners who are more anxious—just like they might struggle to understand yours.

And as queer relationship writer Nora Samaran points out, we unfortunately live in a culture that tends to valorize and masculinize avoidant attachment (think of the “playa” stereotype) while denigrating and feminizing anxiety (think of the “crazy ex-girlfriend” stereotype). 

So how do we solve this problem? Well, partly we don’t. A key aspect of dating is accepting that we will fuck up, get hurt and hurt others, because, paradoxically, this allows us to be more aware of ourselves and hopefully avoid harming our partners in really serious ways. A common example of this is when we avoid breaking up with someone in order to “not hurt their feelings”—a behaviour that might seem compassionate on the surface, but is obviously much more hurtful and detrimental to everyone in the longer term.

A strategy that can help, however, is practicing three basic skills and setting the expectation that our partners or potential partners do the same as soon as we start to feel something potentially romantic happening:

  1. Asking explicitly (and appropriately) for what you want, e.g. “Is it okay that I’m flirting with you?”
  2. Clearly declining what you don’t want, e.g. “I’m really enjoying this date, but I am not looking for anything other than fun sexy times.”
  3. Being honest about when you aren’t sure if you want something or not, e.g. “I’m really loving this vibe and I’m super into you, but I’m not sure if I want things to go any further, and it’ll take me awhile to figure that out.”

These three foundational skills can go a long, long ways toward helping us date and flirt in ethical ways—particularly when we are queer, which means that the line between friendship and flirting can be thin, to say the least.

It’s the simplicity of the above that makes them so difficult; there isn’t really a clever trick to get around the vulnerability of asking for what you want (which carries the fear of rejection), the guilt of declining what you don’t want (which carries the shame of being disappointing) or the awkwardness of declaring that you are still figuring out what you want (which carries the anxiety of needing to have more difficult conversations in the future).

Yet as we practice these skills, they become easier and easier, and so, too, do our romantic lives—which means that I think you ought to be able to continue dating, exploring sexuality and making queer friends fairly successfully so long as you also start to work in explicit communication about what you can and can’t offer.

I think it’s worth mentioning as well that your straight female friends’ experiences may not always provide the best reflections on your own, lesbian experience. Heterosexuality projects certain constraints, dangers and expectations onto the respective roles of women and men—for example, that a woman should wait for a man to make the first move, or to call/text after the first date. The supposed responsibility of a man to lead and guide the relationship comes from the historical precedent that a man should take care of a woman and uphold her virtue—and sometimes, we queers can unconsciously bring these already imperfect values into our own dating adventures in ways that don’t really map onto our lives.

By this, I mean: Why shouldn’t you sleep with someone early on in the relationship? Why should it be seen as hurtful or irresponsible to see more than one person at a time, provided that there is honesty and care extended to everyone involved? Queer life and culture offer us some wonderful alternatives to the straight, monogamous world of conventional heterosexuality, including the opportunity to fuck and date multiple people at once; the key is to be ethical about it. Fortunately, there are many books and articles on the topic of ethical non-monogamy that can help guide you.

Remember: What tends to make people feel that they are being respected, rather than exploited, is honesty. What tends to make people feel safe, rather than disposable, is care and predictability (not in the sense of being boring, but in the sense of staying true to your word). If you are able to offer these things to folks you are seeing, however briefly, then I suspect you will start to feel much more capable of managing the relationships in your life in a way that feels good to you.

So you’re not an alien, AILF. Or rather, perhaps we are all aliens—strange, beautiful, wonderful creatures hoping to find connection on this confusing, weird-ass planet, struggling to understand and be understood. It’s always going to be challenging, always more difficult than we thought it would be. But it’s always going to be worth it: worth the confusion, worth the struggle. You’re always going to be worth it.

In our latest “Ask Kai: Quick Tips for the Apocalypse,” the video series offering relationship advice for those in a hurry, Kai Cheng Thom looks at how to deal with a flirty—but supposedly straight—friend.

Kai Cheng Thom is no longer a registered or practicing mental health professional. The opinions expressed in this column are not intended or implied to be a substitute for professional medical advice, diagnosis or treatment. All content in this column, including, but not limited to, all text, graphics, videos and images, is for general information purposes only. This column, its author, Xtra (including its parent and affiliated companies, as well as their directors, officers, employees, successors and assigns) and any guest authors are not responsible for the accuracy of the information contained in this column or the outcome of following any information provided directly or indirectly from it.


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