This is the 7th 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.

In every high school drama, the football star is the villain, and the mathlete or theater geek is the unsung hero. The nerd predictably gets the girl, or a girl, simply because he’s pure in a way the quarterback could never be—tender, loyal, immune to superficial social pressures. But reality, as it often does, paints a different picture. Just look at the headlines: tech moguls throwing wild, naked pool parties; guys who once coded alone in dark dorm rooms are now living like unhinged Bond villains, with a model, stripper, or cellist in every area code.

Even the ones who married their college sweethearts—the women who loved them back when their biggest flex was a perfectly debugged line of code—end up trading them in for someone shinier. The frizzy-haired girl who stuck through the ramen years? She’s divorced now. His new fiancée? The blonde cheerleader who wouldn’t have looked at him twice when he was still the “before” in a Proactiv commercial.

So if the awkward genius turned playboy feels like a plot twist, maybe it shouldn’t.

Here’s a little secret: nerds are just as susceptible to the pull of power, status, and, well, vengeance, as the cool kids. For many of these men, dating someone beautiful is payback for every girl who rejected them—or, more accurately, didn’t know they existed—in 11th grade. Maybe they didn’t have a prom date back then, but now their Instagram is a buffet of options. The ultimate flex is a pretty girl on his arm, his first baddie. But wouldn’t it be nice if he actually… liked her?

These men crave validation but resent the reminder of who they once were: the invisible kid lurking at the edges of the school dance.

A few years ago I had my first brush with an Undercover Thot. He was a software engineer, a plus-one at a friend’s birthday party, and seemed like he’d never been to a party, let alone a nightclub. At the bar, he spilled cranberry vodka all over my silk Galliano dress. His face flushed bright red—a perfect storm of shame and social ineptitude.

“Oh my God,” he stammered, scrambling for a napkin. “I’m definitely not the smoothest guy. Please, let me pay for dry cleaning—or at least take you to dinner to make up for it?”

(The dinner suggestion was too smooth, now that I think about it.)

He was awkwardly handsome: tall and slouchy, all Adam’s apple and nervous charm, curly hair falling over icy gray eyes (and, yes, thick-rimmed glasses). He looked like he still felt guilty about botching a group science project in 2012. Kind, safe, and non-threatening—a novelty at that point in my life.

In the beginning, he adored me. I was his prize, the girl he never thought he’d pull. Every day, there was a new line: “Wow, I can’t believe you’re mine,” or, “How did I get this lucky?” And then my personal favorite: “You would’ve terrified me in high school.” (So it’s my fault my former self wouldn’t have liked your former self?)

For my birthday, he brought me a Lego flower bouquet. Sweet, I guess—though real roses wouldn’t have killed him. The last guy I dated—a Bushwick tattoo artist—got me a blue raz Elf Bar, so technically, this was progress. Marginal, but progress.

Our dates were curated from a 12-year-old’s dream journal: Dave & Buster’s, the Bronx Zoo, 3D screenings of The Dark Knight. He introduced me to things I never liked and never will—assembling Gundam model kits, Settlers of Catan, anime.

I patted myself on the back for my emotional maturity. Look at me, loving someone for what’s inside! I’d finally broken the cycle: no more devastatingly handsome skaters or DJs texting “wyd” at 2 a.m., summoning me to mattress-on-the-floor walk-ups that reeked of Axe and bong water. This guy was different. A gentleman. A career man. He took me to real dinners, paid for them, and made me feel safe—safe enough that I wasn’t overly curious when he left his unlocked phone on the bed while he showered.

But no harm in checking, right?

The messages were impressive in both range and quantity. He wasn’t just chatting up one porn star on OnlyFans—he was deep in the DMs of several who were specializing in things I can’t even type without feeling the need to find a priest to confess to.  Also, Tinder? Last active three hours earlier, around the time I had gotten up to go to the bathroom during dinner. I stared at the screen, blinking, like I’d been hit by a truck that also reversed back over me.

It felt like finding a cool underground band, only to see it headlining Coachella, or spending $100 on a “true vintage” dress from Depop, only to realize it came from Forever 21’s clearance rack. My safe, socially awkward boyfriend was a supervillain in disguise. Was it possible to sue for emotional damages?

So, here’s my spicy take: conventionally hot, popular guys deserve a little more credit. Sure, they might hook up with two girls in one weekend, treat the bro code like the Ten Commandments, and spend more time meal prepping than reading—but at least they’re honest about it. There’s no false advertising. What you see is, for better or worse, exactly what you get.

The real danger is the guy you think you’re safe with. The one who initially looks at you like you’re the first sunset he’s ever seen. Because when the awe fades, you’re just a walking trigger for bad high school memories. No one hungers quite like a man who’s spent years eating metaphorical crumbs.

In my case, the downward spiral started with passive-aggressive jabs—my nail polish was chipped, the novel I was reading was stupid—and then it went full tilt. The “safe guy” can turn out to be a Trojan horse of betrayal. And when it hits, it hits. One minute you’re pinning wedding venues on Pinterest; the next, you’re clutching a bottle of Nair and Googling, “How long does it take for eyebrows to grow back?”

But this isn’t an anti-nerd manifesto. The takeaway isn’t: “Never trust a guy who owns a Lord of the Rings box set.” It’s: “Never trust a guy just because he owns a Lord of the Rings box set,” or because he’s frail-lanky, has a rodent face, reads you poetry, or possesses any other qualities women mistakenly read as “safe.” Villains don’t always wear capes; sometimes they wear Warby Parkers and ask if you want to go to a Dungeons & Dragons live show. Whether he’s a hot DJ in Chrome Hearts or an angsty tech bro in Allbirds, men will be men, and masks will slip. And when they do? Don’t act shocked. We all saw what happened with the man formerly known as SpongeBob SquarePants.

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
Once Upon a Cosplay
Confessions of a Love Bomber