Let’s talk about the sassy boy. A species of man whose emergence marks the slow, glittery collapse of traditional masculinity and the simultaneous rise of emotionally literate male narcissism. Picture a guy who listens to FKA Twigs and Jordan Peterson. He’s flirty, ironic, and deeply online. Sassy boys are here and they’re reclaiming romance as performance art, equal parts court jester and cult leader.
But I’m getting ahead of myself.
It started on Halloween. Which, of course, is where all bad stories begin… a holiday of delusion, slutdom, and spiritual decay. I was at a party full of costumed strangers and sticky floors, sauced in an untasteful way. A lukewarm White Claw that definitely wasn’t mine in my hand. I remember flashes: someone dressed like Rick Owens if Rick Owens worked at a vape shop, me pretending to know people I’ve blocked on Instagram.
Enter: the boy. Dressed as a Peaky Blinder. Not a half-hearted attempt, either. Full vest and cap. The look said, I romanticize organized crime and probably microdose. I was intrigued.
We chat. He’s charming in the way only an overeducated boy in a silly hat can be. I don’t get his number. I don’t follow him on anything. There’s a weird purity in the moment. Like, whatever. He was cute. I’ll never see him again.
Cut to three months later.
He follows me on Instagram. Unprompted. Out of the blue.
And then, the message:
“So like… when were you planning on asking me on a date, or is that my job?”
Pause. Breathe. Process.
What is that? A power play? A joke? A threat?
This is textbook Sassy Boy Syndrome. A psychological condition marked by excessive self-awareness and a weaponized knowledge of attachment theory.
Let me be clear: a sassy boy is not a softboy (too apologetic, too soylent-coded). He is not a fuckboy (too lazy, too boring). A sassy boy is an entirely new archetype. They’re charming, but not in a traditional sense—more like they’ve studied charm as a concept and are now doing a very self-aware interpretation of it. They’re emotionally literate but only in the way a guy becomes after watching four hours of TikToks about girlhood. They say things like “feminine rage is so valid,” and then disappear for six days.
So naturally, I ignore the message. For a month. Not out of malice, just out of instinct. I mean, what does one even do with that? Eventually, I respond. We banter. He suggests we go out. I say sure. He says he’ll “get back to me with an itinerary.”
An itinerary. Not a plan. Not a time and place. An itinerary.
And a week later—because nothing in this man’s universe moves at a normal pace—he sends the big reveal:
“We should go on a picnic and see a movie.”
A picnic.
Excuse me?
You want me to picnic with you? In public? In broad daylight? You think I’m going to sit on a blanket like some Victorian farm wife while you watch me chew brie and crackers with your little corduroy pants rolled up? You think I’ve earned the right to be perceived while eating in natural light with a stranger I haven’t even seen sober?
It’s the theatricality of it that gets me. The pageantry. The delusion that this is romantic, not horrifying. A picnic is something you graduate to, not a first date. This isn’t Pride and Prejudice. This is delusion in a Carhartt beanie.
So I do what any rational woman would do: I panic. And I ghost.
Because at the end of the day, the sassy boy is exhausting. He wants to be hot, ironic, and emotionally impressive; he wants to win the vibe war. He treats dating like it’s immersive theater. He doesn’t want to know you, he wants to be seen knowing how to date you.
And frankly, I don’t have the time. I wasn’t avoiding him—I was exercising the only boundary I had left: total disassociation.
Sassy boy summer is not for the faint of heart. It’s a battlefield. A fever dream. Gender studies LARPers sent to emotionally destabilize you under the guise of “inner work.”
Stay strong out there.
spring break 