It’s not the kind of question you expect to see outside a nineteenth-century novel, or a slightly unhinged period drama. Yet there it was, a tiny message in the chat.

For a moment, I assumed it was a joke. The kind of joke people make when trying to say something awkward without really saying it. Unless it wasn’t a joke. And, as the conversation unfolded, what initially sounded like a relic from another century started to feel strangely modern. Beneath the theatrical wording was something deeply familiar to anyone navigating love in their late twenties or early thirties. A carefully designed arrangement meant to avoid one thing above all else. A decision, not a breakup. And more than anything, not a relationship. Just a comfortable grey zone where nobody has to commit to anything irreversible.

If there is one skill many Zillennials have quietly perfected, it is the art of not deciding. We grew up in the golden age of options. Streaming platforms replaced television schedules, dating apps replaced chance encounters, and careers became something you could pivot from every two years with a mildly inspirational LinkedIn post. Choice was supposed to be liberation. Instead, it quietly became paralysing. Love, unfortunately, did not escape the trend. Modern relationships often resemble browser tabs left open too long. There is the person you are seeing, the person you used to see but might see again “when things calm down,” the person you occasionally text after midnight, and the person in that ambiguous category known as potential. Nothing is fully closed. Nothing is entirely open either.

Previous generations approached relationships with a kind of brutal clarity. You were together, or you were not. You married, or you didn’t. The rules were rigid and often unfair, but at least they were comprehensible. Our generation inherited something better, and far more complicated. Freedom. Freedom to choose partners, freedom to leave, and freedom to redefine what relationships even mean. But freedom comes with a small, inconvenient requirement, someone eventually has to choose. And that is where things start to get messy. If you grow up believing there is always a better option somewhere, a better job, better city, better match one swipe away, every decision begins to feel slightly premature. What if the right person arrives next year? What if you commit too early? What if this relationship works… but not perfectly?

In response, we have developed an impressive catalogue of relational middle grounds. Situationships, undefined things, emotional arrangements governed by rules so subtle that nobody can fully explain them, yet everyone understands instinctively. You are not exactly together. But you are also not exactly free. Sometimes people simply can’t decide in front of all those possibilities. Therefore, on one hand, they see someone and are “more or less” together. And on the other hand, they see other people too.

The “Do you want to be my mistress?” message was, in its strange way, a more honest version of this logic. At least I knew I was the only unofficial one. It was not villainy. It was the proposal of someone trying to engineer intimacy while postponing commitment indefinitely. A relationship with built-in emergency exits. The irony is that Zillennials are, by most accounts, highly self-aware. We discuss attachment styles like amateur psychologists. We read essays about emotional labour. We listen to podcasts explaining why we behave exactly the way we do. 

Understanding the problem, however, has not made us better at solving it. Because the real difficulty with love has never been understanding it. The real difficulty is accepting a small, uncomfortable truth. Every meaningful relationship eventually requires one thing. A decision. And decisions have a tragic side effect. They eliminate all the other possibilities. For a generation raised on the promise that everything should remain open, that can feel like a small catastrophe. So, we negotiate softer arrangements. We design flexible connections. We construct relationships that allow us to stay emotionally close while technically remaining available for something else.

Mistresses, situationships, ambiguous almost-relationships, they are all variations of the same modern invention. They are what happens when a generation raised on infinite options collides with the ancient and inconvenient reality of love. Because, despite all the apps, theories, and carefully negotiated grey zones, relationships still require one surprisingly old-fashioned gesture. Someone, at some point, has to choose. Preferably in a way slightly more romantic than asking, “Do you want to be my mistress?”

And let’s remember, karma is real. You don’t want to be the unofficial one. For your sake. For the official one’s sake. And for integrity in general. If you want to be with someone, go full on. But don’t linger in between, sending texts at 1 a.m. every few weeks to remind them you “think a lot about them.”

With Love, Chaos, and Jazz. Always