The Moment That Started It All

Their on-screen friendship didn’t just evolve overnight. In fact, one of the most memorable moments occurred in 2022 during a commercial break when Dana Perino teased Gutfeld for mispronouncing the word “Schadenfreude” in a debate. Instead of retreating into his usual sarcastic humor, Gutfeld responded in a way only he could: he scribbled the word phonetically on a notepad and drew himself in a dunce cap. Then, he slid the note across the table to Perino.

The result? A burst of uncontrollable laughter from Perino, who found herself wiping away tears when the cameras resumed. Gutfeld, deadpan as ever, continued with the segment, but the moment of genuine camaraderie was impossible to ignore. It wasn’t just the humor of the situation—it was the authenticity. Fans saw a side of the duo that was rare for television: an unforced, natural bond that made them more relatable and real. Clips of the moment quickly spread online, earning a special place in viewers’ hearts. But this was only the beginning.

Acts of Kindness Beyond the Spotlight

Their relationship didn’t stop at jokes during breaks. Over time, the pair’s friendship evolved into something far more personal. One of the most touching instances came when Perino lost her beloved dog, Jasper. Gutfeld, known for his sarcastic and often brash humor, revealed a much softer side when he quietly arranged for meals to be delivered to Perino’s home every night for a week. For someone like Perino, who tends to be reserved about personal matters, this gesture spoke volumes.

Later, on-air, Gutfeld brushed it off with his usual humor, quipping, “I just didn’t want you living on wine and pretzels.” But Perino, visibly touched, admitted that it was one of the kindest things anyone had ever done for her. The sincerity behind Gutfeld’s actions was undeniable, and it only deepened their bond.

Months later, when Gutfeld underwent minor surgery, Perino showed her loyalty in return. She sent him crossword puzzles, including a note that read, “Don’t cheat — Jesse will know.” Gutfeld later credited the puzzles with helping him maintain his sanity during recovery, underscoring just how much the small, thoughtful gestures between them mattered.

Mischief and Fun: Off-Camera Antics

Of course, not everything was serious. Dana Perino and Greg Gutfeld also know how to have fun. At the 2023 Fox holiday party, Perino dared Gutfeld to take the karaoke stage. What followed was a performance that no one expected: Gutfeld’s over-the-top Elvis rendition of a classic hit. Perino, standing in the front row, swooned dramatically, feeding into the crowd’s laughter. But the fun didn’t stop there. Later, Perino joined him for a duet of I Got You Babe, leading to the crowd dubbing them the “Sonny and Cher of cable news.” The moment was a lighthearted celebration of their playful chemistry, showing fans another side of their friendship—one that was full of spontaneous joy.

But even in their playful antics, there’s an underlying loyalty. For example, when Gutfeld swapped Perino’s on-air water with sparkling tonic, she shot him a live glare and muttered, “You’re dead to me, Greg,” before dissolving into laughter. In return, Perino made her mark weeks later by sneaking Post-it notes onto Gutfeld’s desk, each one carrying mock rules like, “No interrupting me today.”

It’s these moments of mischief that make their relationship feel authentic. They poke fun at each other, but always with an understanding that, when the chips are down, they’ve got each other’s backs. The dynamic is full of humor, but beneath the surface is the unspoken trust and mutual respect that defines their off-camera friendship.

The Heart of The Five: Unscripted Chemistry

What makes the relationship between Greg Gutfeld and Dana Perino so special is how it transcends the usual camaraderie of a typical newsroom. It’s not just about joking around or keeping things light—it’s about building a true friendship that fans can see through the lens of their TV screens. Their chemistry isn’t scripted, nor is it polished for the cameras. It’s raw, genuine, and all the more captivating because it is.

Fans of The Five often refer to Gutfeld and Perino as the heart of the show. Their interactions, both on and off-air, have become a central part of what makes the show feel unique. They balance each other perfectly: Gutfeld, with his biting humor and irreverence, and Perino, with her level-headed wisdom and calm demeanor. Together, they create a dynamic that feels like an inside joke shared between long-time friends.

When the show’s debates get heated or when the topics grow contentious, Gutfeld and Perino are quick to back each other up. It’s in these moments that viewers see the strength of their bond. They’re not just colleagues—they’re friends, and it’s clear they genuinely care for one another. Their friendship provides a layer of warmth to the sometimes tense discussions, reminding fans that even in the polarized world of political commentary, genuine connections can exist.

A Bond Beyond the Screen

As much as their friendship is visible on-air, it’s clear that the connection between Gutfeld and Perino extends far beyond the cameras. The quiet moments of support, the shared laughter during breaks, and the thoughtful gestures show that their relationship is built on more than just good TV. It’s about loyalty, respect, and a genuine care for each other’s well-being.

Their off-camera friendship has become a rare gem in the world of television—one that fans continue to appreciate. It’s the kind of bond that transcends the usual celebrity connections, grounded in authenticity and a shared love for humor, camaraderie, and the work they do together on The Five.

A Friendship That Fans Can’t Get Enough Of

Dana Perino and Greg Gutfeld’s friendship has become one of the most beloved aspects of The Five. Fans continue to delight in their banter, cheer for their mutual respect, and relish in the unexpected moments of humor that occur between them. Whether it’s a mischievous prank, a heartfelt gesture, or an unscripted moment of laughter, viewers can’t get enough of their dynamic.

This friendship is a reminder that, behind the polished news segments and political debates, there are real relationships at play. The friendship between Gutfeld and Perino is a testament to the power of genuine connection in an industry often known for its cutthroat competition. It’s a reminder that, even in the high-stakes world of cable news, warmth, loyalty, and laughter still have a place.