This is the fifth installment of 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.

At the opening of a 22-year-old’s show at a Chelsea gallery—a sculptor with all the intensity of someone who’d just discovered Rodin—I spotted my dream guy across the room.

 “Who’s that?” I whispered to the girl beside me, my eyes fixed on his disheveled curls and plum-colored Loro Piana blazer.

 “Yeah, good luck,” she scoffed. “That’s ____—a European royal (keeping it vague to protect the innocent). “He just moved here. But don’t even try.. He’s practically untouchable.”

After a few glasses of rosé, I mustered up the courage to introduce myself. Turns out, he wasn’t the snob I imagined. He was charming, handsome, polite—the whole trifecta. After a long conversation, I’d snagged his number but no date. In the Uber home, I decided to shoot my shot.

So nice meeting you. We should grab a drink sometime.

He responded within seconds: I’d like that. Next week work? I’ll book a spot for us 🙂

I immediately called Chloe, raving about my soon-to-be titled boyfriend. I needed her guidance—Chloe, Jedi Master of effortless allure, queen of making men obsess. While I’m all sharp edges and chaos, she’s polished perfection. Bagging Prince Charming was one thing; keeping him would require some serious strategy.

“We’re going to have to play this very carefully,” Chloe advised. (She, too, wanted an invite to the palace.) “This guy’s used to being fawned over. You have to be different. You need to be… chill.”

Chill? The closest I’d come to that was putting ice in my martini. But for Prince Charming, I was willing to give “chill” my best shot.

 For our first date, I swapped my usual vintage corset for a turtleneck. (Chloe swore by the “Sweater Theory”—on first dates, dress down.) Whether it was my modest fit or my undeniable charm, it worked—he asked me out again. Not long after, we were officially a thing.

I became the embodiment of the Chill Girl—cool on the surface, Olympic-level discipline beneath. I ditched the animal print and miniskirts and reinvented myself as Kate Middleton’s edgier cousin. Think sleek trench coats, vintage Prada dresses, high ponytails, and that “I’m not trying” kind of makeup that takes an hour to perfect. When he lost his phone in an Uber, I handled the entire rescue operation in under 20 minutes. When he complained about being hungry, I made him food (Doordashed and reheated, but he had no clue). When he canceled plans last minute, I was sweetly understanding. I mirrored his personality while secretly studying fork placement. I was the girl who laughed at his jokes, even the dumb ones, watched his favorite movies (Fight Club), and somehow convinced myself I was into his questionable music choices (tropical house).

By week three, he was all in. “You’re so low-maintenance,” he said with a dreamy smile, which was like calling a lion a house cat. “It’s just so easy with you. You’re amazing.”  By week four, after a boozy dinner at Bar Pitti, he turned to me, eyes wide, and said, “I’m not interested in seeing other people.” “Me neither,” I replied, possibly too quickly.

Mission accomplished. I was halfway to royalty, picking out outfits for an (imaginary) Alpine ski trip. Just one little problem: I was exhausted. Cosplaying “Chill Girl” was a full-time job. I was on 24/7, nodding and smiling nonstop, keeping my quirks under wraps, and deep-breathing through mood swings. As someone who can have a rage blackout while looking for a missing shoe, it was harder for me than most.

Then, on week five, came my royal slip-up. At Odeon, a middle-aged guy stormed over to our table. “Not cool to smoke inside,” he snapped, glaring at my vape. “You’re setting a terrible example for my teenage daughter.” I should have shrugged it off, but after that much vodka, no one was safe.

“Not cool to be such a Karen,” I shot back. “And with a father like you, your daughter’s going to be onto far worse things than vaping by the time she’s my age.”

 Prince Charming looked appalled.

“That was… so not like you,” he said with a shaky little laugh.

Actually, I wanted to reply, it’s exactly like me. But I bit my tongue, flashed a breezy smile, and somehow skated on. Close call. I knew from that moment on I needed to be extra careful, so I doubled down on my Chill Girl routine.

But then came the red flags, in bulk: “funny” memes he just had to send to his ex, spontaneous “work trips” with vague details, my concerns waved off with continental indifference. My friends were baffled by my sudden transformation. The “new me” seemed suspiciously like a doormat. But I knew if I so much as hinted at making life less than blissfully easy for Prince Charming, I’d be history.

“Then maybe that’s not a relationship,” my friends pointed out. Fair, but was I really going to bow out without ever seeing the palace?

When he ditched me for another one of his “work trips,” only for Instagram to reveal a beach party with Dom Pérignon and Euro models, I finally decided it was time to confront him.

“You lied,” I snapped.

He looked at me like I’d staged a palace coup. A few weeks later, the resentment I’d swallowed spilled over at a party, where, lo and behold, his ex was perched over his lap, laughing like she was auditioning for the role of Loyal Concubine #1.

“We’ve been best friends since birth,” he groaned when I confronted him. “You’re acting crazy. I can’t date someone so jealous.”

Right, and I couldn’t date someone who’s “best friends” with his ex. Or with any girl, for that matter.

One morning while making coffee, he casually mentioned he was moving back home. “Not sure long distance makes sense for me right now,” he said with unerring politeness. “Do you want sugar?”

Is Xanax an option?

Sure, we didn’t even hit the three-month mark, but he’ll forever be my “royal ex”—the one I’ll name-drop to my kids someday. Because if you’re going to break your own heart, at least do it with someone who makes for a fantastic story. And while I didn’t walk away with a tiara, I did get a hard-earned life lesson: Cosplaying works—until it doesn’t. Eventually, you have to ask yourself: is it worth becoming someone else for a man who wouldn’t lift a finger for the real you? Because playing perfect doesn’t make him love you more—it just makes you lose yourself.

So, Prince Charming, if you’re reading this, consider this my formal apology for the whole charade. But if you’re ever short a date for the ball, don’t worry—I’ll come and be on my absolute fakest behavior.

Catch up on Dating, Unhinged:

The Noah Effect: Are Nice Guys Finally Trending?
How (Not) To Get Your Ex Back
The Crazy-Hot Matrix, Explained
To Ghost or Not to Ghost