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.

Women are trained to soothe and save. We apologize when someone bumps into us. We give men the benefit of the doubt: psychoanalyzing, excavating childhood traumas, writing dissertations on why they ghosted us. Despite our best instincts, we can sometimes default to willful ignorance. We don’t just forgive them; we mother them. We swaddle adult men in excuses until they’re practically back in Pampers. And nothing activates the empathy circuit board faster than tears.

Sensitive men read as safe, evolved, feminist-approved—the antidote to frat bros and finance guys. We don’t want the alpha; we want the poet in skinny jeans, the guywho listens to Elliott Smith, the one who blames his inability to commit on that one girl who broke his heart when he was twelve. We convince ourselves that tears are proof of goodness, when really they’re just proof of plumbing.

Up until very recently, I had a zero-tolerance policy toward cheating. I used to judge women who went back to cheaters—girls from college, coworkers, all making the shocking choice to return to men who publicly and repeatedly humiliated them. There was one in particular (let’s call her Claire) whose boyfriend betrayed her with such rigor and regularity it was basically a side hustle. Random club make outs, emotional affairs, DMs multiplying like gnats. She knew, and she stayed.

“She’s doing it to herself,” I’d say, smug on my moral high ground.

“You don’t get it,” a friend told me. “Until you’ve been cheated on, you don’t understand.”

A few years ago, I met the guy I thought I’d marry. He was handsome in a JFK Jr. way—wealthy but lowkey (trust-fund, tattered-tee style)—and for once, mom and dad approved. After years of dating every beanie wearing Dimes Square drummer in the city, I finally found someone who didn’t fist-bump my parents hello. It felt like everything I’d been manifesting for myself since I was twelve, and the first few months were pure bliss. He praised my writing, my hair, my body, my style with unprompted, poetic specificity. On my birthday, he sent three dozen roses and a handwritten love letter, telling me my smile could save the world. Never a flicker of irritation—just mutual adoration. I thought fate had finally arrived. That all the men before him had been training wheels for this: this spectacular, cinematic love.

Month four, over an Omakase dinner, his phone lit up with a notification from Telegram (basically the Silk Road of messaging apps—never a good sign), and he quickly flipped it over, face down on the table, and gave me a long, plunging kiss.

Later, when he was asleep, I typed in his extremely creative password (1234—don’t ask how I knew) and opened Pandora’s inbox. What I found was not just shocking, it was heartbreaking. There were hotel meetups, wire transfers, women named “Baby V,” OnlyFans receipts, exchanges of explicit photos with strangers. It wasn’t simple cheating—it took operational expertise.

I confronted him expecting anger, denial, gaslighting. Instead, he shrank. And then the sobs came. Not mine—his. Not just a tear or two: convulsing, fetal position, choking on apologies. He cited childhood trauma, his dad’s affairs, being bullied in middle school. Then sex addiction. Then a borderline personality disorder he’d forgotten to mention. His desire to ruin something because he felt I was so good, he didn’t deserve it. His long pattern of self-destruction, how much he hated himself, how he woke up most mornings in a stew of despair.

His pain was so apparent, I convinced myself it meant something. His tears indicated remorse, and remorse meant he was not a bad person—just a damaged one.

It became frustratingly hard to label him as a narcissist or manipulator—not because the facts didn’t line up (they did)—but because his vulnerability was so obvious that doubting it felt cruel, like a slur. He didn’t raise his voice, didn’t neg me, didn’t insult my intelligence or call me “crazy” or “overbearing” (classic moves in the narcissist’s playbook). He was unerringly gentle—something that had drawn me to him in the first place. He didn’t even do the thing where he turned my justified anger about his cheating into an argument about my violating his boundaries, an “invasion of privacy.” Instead, he gave me a narrative. A trauma. Suddenly, the story was no longer “look what I did to you,” but “look what’s been done to me.”

Love can sometimes be pure projection, a theoretical exercise. So I found myself, for the first time ever, abandoning any logical response to his betrayal (rage, boundaries, blocking him on everything and never speaking to him again) in favor of compassion. I assume that’s also what Claire did, if I had to guess. You find yourself transmuting the pain of betrayal into a desperate need to become the nurse, the fixer, the one who finally heals the broken boy inside the man who just slept with someone else in a Marriott in midtown at two o’clock in the afternoon. I didn’t see it for what it was (a performance, a deflection) but as a cry for help. His tears, shaking hands, panic attacks, self-loathing—it was all so believable, so convincingly human. I was paralyzed by his pain.

Enter covert narcissism: the most dangerous type of manipulation. It’s not the overtly sociopathic kind we all know well, but the kind that weaponizes pity and uses your compassion against you. The kind that doesn’t say, “You’re crazy,” but “Please try and understand me.” It’s the kind that invites you to sit in the wreckage it caused and then makes you feel guilty for wanting to leave. Because what kind of monster walks away from someone so obviously broken?

After I caught him, he spiraled into depression: no eating, no sleeping, no gym—basically a doomsday scenario. I spoon-fed him courage, nursed him back to life, and burned myself out in the process. And when he finally emerged, he told me I was “the one.” That I’d broken the cycle.

My friends were understandably baffled—perturbed by the fact that I was still in a relationship with this supervillain. I had become that girl. The girl we used to talk about in half-whispers over martinis, our performative concern masking our snark: Can you believe she’s still with him? And yet here I was, embodying the very person I used to judge. 

I told them I was “figuring it out” and promised I would break up with him eventually. But when two weeks turned into a month and I was still blissfully floating on like nothing had happened, they staged an intervention.

It wasn’t about how much I loved him—it was about my health, they insisted. He was clearly reckless in his choices. Why did I want to be with someone who looked me in the face and lied, even if by omission? Who cared why he did what he did? Didn’t I want my wedding guests to be happy for me, not pity me? I told myself they didn’t get it—they hadn’t seen him sob in my lap for hours about his father (or his mother, or his shame, or the puppy that died when he was three—the narratives blurred; the rationalizations became more elaborate). They didn’t know that I was his last tether to this cruel world.

I left the hangout feeling angry. Not just at them, but at how small and exposed I felt. I went straight to his place. And when he fell asleep, I did the thing I told myself I wouldn’t do again: I checked his phone. (The fact that he made it so easy raised another set of questions.) Lo and behold, Tinder was redownloaded, and texts with women were in his “recently deleted.” All those tears, those panic attacks, those speeches about being broken, his tearful gratitude for me saving him—just gambits to buy more time.

I see this play out constantly with my friends and their boyfriends. Just last week, a friend called me in a fit of frustration. Her seven-month situationship, who had already told her he loved her, still wouldn’t commit to being exclusive. By the end of the call, she was fired up.

“You’re right, I’m going to end it,” she said, after my much-needed tough-love pep talk. Finally, I thought. Breakthrough.

An hour later, I called back, ready for a victory lap. Instead, she answered her phone with a lilt in her voice—not the energy of a woman who’d just dumped her man-child.

“What happened?” I asked.

“He started crying,” she said, compassion as thick as honey. She launched into his sob story about the girl who “ruined love” for him freshman year. (He’s thirty-five, by the way.)

I knew exactly what had happened: he’d used tears as his get-out-of-jail-free card. And it worked. Even my brilliant, stubborn friend folded.

While women who cry are seen as needy, manipulative, unstable, and, most of all, annoying, we’re taught, by cultural tropes, books, and movies, that a crying man is a rare and profound creature, sensitive and brave. And depending on the context, that can be true. Emotional depth and vulnerability in men should be cherished.

The problem is, the moment he starts crying, we stop thinking. So hold onto your empathy, girls. And the next time someone tries to weep their way out of trouble, head straight for the exit.