This is Dating, Unhinged, an exclusive series for PLAYBOY from writer, model and viral content creator Isabel Timerman — better known to her loyal followers as IsabelUnhinged. She started posting videos in 2022, using social media as an outlet after a messy breakup. With her candid, painfully relatable posts, she quickly amassed a devoted following and millions of views. Now crowned the “Empress of Delululand,” she leads the delulu movement, encouraging women to embrace their fantasies with humor and positivity. Her satirical yet honest approach to dating has made her a powerful voice for those seeking empowerment through unfiltered authenticity.

My love language used to be sarcasm. I mocked myself before others had the chance to, which, in the context of modern dating, felt less like a flaw than a strategy. Around men I liked, I often downplayed my successes, shrank my dreams and made myself smaller. On first dates, when asked about my hobbies and passions, I’d say: “Drinking. Vaping. Rotting in bed.” Some laughed. Others bolted.

For years, I sincerely believed that “roasting equals flirting.” If I made myself the punchline, my date could join in, and we’d volley insults back and forth. Banter ramped up the chemistry and meant we “got” each other; the ultimate icebreaker. I’d come across as chill, vaguely chaotic and utterly unthreatening. A girl who didn’t take herself too seriously.

The irony was: I did like myself. I was proud of my work, my style, my writing. I knew I was interesting. But around men, I’d turn into a lovable mess. A spectacle, but a charming one. A disaster, but a hot one. Maybe, subconsciously, I was begging to be rescued. If I could prove just how broken I was, someone would swoop in and save me. Or maybe I’d just internalized the fear that confident women turn men off, creating a character that was a bit too comfortable to play.

The dates went well, if they laughed. If they didn’t, I worried I was too much. Too loud. Too honest. Too… me. Still, I convinced myself that being funny was my invisible shield. I’ll put myself down, so they can’t. 

But they can, and they will.

A few years ago, I started dating a guy who was on the brink of stardom. A lo-fi musician with a hit song that blew up on TikTok and quickly climbed the charts. He didn’t become famous so much as metabolized by fame, giddy with it, humming with a new kind of attention I knew would never, ever include me.

I wasn’t on magazine covers or walking red carpets in fedoras, but I had accomplishments of my own. Fans, readers, a manager who believed in me. Girls on the street told me I’d changed their lives (or at least made them feel slightly less alone while spiraling because a guy viewed their stories while actively ignoring their texts). But instead of showing up in that relationship with pride, I turned it into stand-up. I joked about being unproductive, about hating everything I wrote, about my string of evil, deadbeat ex-boyfriends. I made myself sound unserious, lazy, and lost.

“You get Prada, I get Claire’s,” I said, referencing the teen jewelry store and the designer backpack he got comped in the same breath. And we’d laugh so hard our abs would hurt.

What I didn’t know then was that this was the beginning of a dangerous pattern. With him, I started writing myself out of my own story. I became the sidekick, the comic relief. My career became a punchline. My ambition dissolved into irony. I stopped trying to impress him and started performing inadequacy instead, because it felt so much safer to be nothing. He never told me I was nothing. He didn’t have to. I did the work for him. I told myself I admired his confidence, which, looking back, was far more fragile than mine, held up by props and attitude.

Soon, self-deprecation became self-defeat. And he was more than happy to pile on, using my own words against me. “You’re so lazy,” he’d say when I complained about my career. “Why don’t you just become a supermodel or something?” A jibe wrapped in a joke.

It became increasingly clear: I wasn’t famous enough for him. Not glamorous enough. Not legible enough in the hollow world he so desperately wanted to exist in.

One night, while lying in bed, he said: “I don’t want to tell people we’re dating because I don’t know how to explain what you do.”

And I, who considered myself a writer, creative, a sometimes model, a niche viral internet sensation, had absolutely no idea how to defend myself. I’d handed him the script I’d written. What could I say now? “Wait, I was just kidding!”

A few months in, I finally worked up the courage to confront him. I told him his so-called jokes, about my laziness, my “little TikTok thing,”  and my lack of fame, weren’t all that funny. They were starting to hurt. I told him it felt like he didn’t take me seriously and downplayed everything I’d accomplished. In full regalia, leather jacket and designer shades, he looked at me with annoyance bordering on contempt and said something that stopped me cold: “You say those things about yourself.”

He was one hundred percent right.

“That’s why I never go there,” my best friend Ava responded when I recounted the incident. “When you put yourself down, you’re giving people permission to join in.”

Ava never trash talks herself in front of the men she dates, not even as a joke. Not because she takes herself too seriously, but because she knows it lowers her value in their eyes. It feels like power, at first. Humor always does. But there’s a fine line between humility and humiliation, between “haha I’m such a mess!” and “wait, do you actually think I’m pathetic?”

Eventually, I realized the damage was done. I’d self-deprecated my way into a dynamic I couldn’t get out of. Yes, he was more successful. Yes, his career was further along. But maybe, just maybe, if I’d simply been my slightly delusional authentic self, things would’ve gone differently. Not well, I fear, but differently.

The truth is, power matters in even the best relationships, and you can’t take respect for granted. No one wants to date the girl who hates herself out loud, even in jest. And I didn’t like that girl either.

I’ll never stop loving banter, and I still can take and make a joke. Just not at my own expense. (Unless it’s for TikTok, of course).