Greg Gutfeld’s Second Baby’s Early Birthday Party Brings The Five Together — And One Special Guest Steals the Show

Greg Gutfeld, Fox News’s famously sharp-tongued late-night host and co-host of The Five, has long kept his private life away from the public eye. Known for his biting humor, sarcasm, and satirical commentary, Gutfeld rarely lets fans glimpse the man behind the wit. But this past weekend, the curtains briefly parted, revealing a side of Greg rarely seen: a devoted family man celebrating the early birthday of his second child. What started as an intimate, low-key gathering soon transformed into a heartwarming reunion of The Five cast—and featured an unexpected surprise guest who left everyone speechless.

An Intimate Affair with Fox News’ Closest-Knit Crew

The party took place at the Gutfeld family’s countryside home just north of New York City. Despite the beautiful rustic setting—with soft string lights twinkling in the trees, pastel balloons gently swaying in the breeze, and picnic tables dressed in understated but elegant decor—the event was planned to be a modest, private affair focused on family and close friends.

Elena Moussa, Greg’s wife, reportedly took charge of the preparations. A small acoustic band softly played lullaby-style jazz, setting the perfect backdrop for an afternoon meant for quiet celebration and childhood joy.

Yet, the guest list was anything but modest. The entire cast of The Five came to celebrate alongside the Gutfelds. Dana Perino was the first to arrive, carrying a custom-made baby quilt embroidered with the baby’s name—which, intriguingly, has been kept under wraps. Following her was Jesse Watters, who brought his children, turning the backyard into a playful scene filled with laughter and energy. Jeanine Pirro, known for her fierce courtroom presence, surprised guests by joking as she held a silver rattle wrapped in a ribbon: “It’s the only thing I’ve ever held that’s not a gavel.” Even Tyrus, Fox News’s larger-than-life personality, arrived with a giant plush dinosaur that quickly became the party’s unofficial mascot.

What was clear from the start was that these weren’t just coworkers making a perfunctory appearance—they were genuinely engaged, holding the baby, chatting warmly, and savoring the rare chance to celebrate outside the studio.

Greg Gutfeld: The Satire King Turns Proud Dad

Known for his quick wit and sarcastic commentary, Greg was unrecognizable to many that day—not as the sharp-tongued late-night host, but as a loving father. He wore a simple T-shirt emblazoned with “#DadLife,” his sneakers speckled with baby food stains, and a wide, genuine smile that lit up the gathering.

“He was a different Greg,” said one attendee. “The same humor, but with a warmth you don’t usually see on TV. He wasn’t performing for the cameras. He was just… happy.”

Even in this tender moment, Greg couldn’t resist a bit of humor. When the mood softened, he quipped, “You all thought I didn’t have a soul. Turns out it was hiding under diapers and teething rings.” Laughter bubbled up among the guests, blending perfectly with the afternoon’s emotional undercurrent.

The Surprise Guest Who Stole Everyone’s Heart

The celebration was already memorable, but then came the moment no one saw coming. As the group gathered around the picnic table to enjoy cake, the garden gate opened, revealing a special visitor: a local children’s entertainer dressed as Paddington Bear.

With his soft paws, blue coat, and trademark red hat, Paddington ambled through the crowd, enchanting the children and adults alike. But what made the moment extraordinary wasn’t just the appearance of the beloved literary character—it was what Paddington carried with him.

Reaching into his satchel, Paddington pulled out a neatly folded letter sealed with wax. Greg, intrigued, opened the note and slowly read its contents. Written by his eldest child with help from Elena, the letter read:

“Dear Baby Brother,
Happy almost birthday! You don’t know it yet, but you have the best dad ever. He reads silly books and makes the best bear voices. I can’t wait to share him with you.
Love, your sister.”

The sight of Greg’s usually stoic face softening, tears welling in his eyes, was a rare and touching moment. Attendees say they had never seen him so moved, on-camera or off. Overcome with emotion, he embraced Elena, who whispered, “Surprise.”

Guests erupted into applause, witnessing a genuine display of love and family that transcended any political or media persona.

“It was the sweetest moment I’ve ever seen at any party—Fox or otherwise,” one guest reflected. “That letter. That bear. Greg’s face. It was like watching a man realize how truly lucky he is.”

Paddington Bear and The Five: The Crossover No One Expected

From that moment on, Paddington Bear was the star of the party. Dana Perino was seen playfully pretending to sip tea with Paddington, while Jesse Watters balanced his toddler on one arm and the bear on the other. Greg, known for his sharp wit and quick quips, was caught in rare candid photos crouching next to Paddington, smiling softly in a way his fans rarely witness on air.

Though no official Fox News cameras recorded the event, several attendees shared photos on social media—carefully edited to protect the children’s privacy. One fan-favorite shot captured Tyrus hugging Paddington while holding a slice of birthday cake, captioned, “Cuteness over chaos. Even Greg can’t joke his way out of this moment.”

Fans React: “We Need More of This Greg!”

News of the party’s surprise went viral among fans of Gutfeld and The Five. Social media was flooded with reactions ranging from delight to admiration.

One fan tweeted, “Greg Gutfeld planning a Paddington Bear-themed baby party was not on my 2025 bingo card, but I’m HERE for it.”

Another joked, “Now THIS is the Fox News crossover episode I didn’t know I needed.”

Many fans praised the camaraderie of The Five cast, noting how the event revealed a genuine, supportive found family. One follower commented, “Say what you want about their politics, but that is a found family if I’ve ever seen one. Greg clearly loves his wife, his kids, and his crew.”

A Glimpse Behind the Scenes: Greg Gutfeld’s Growing Family

While Greg’s on-air persona is sharp, witty, and often irreverent, the early birthday party showed a different side: a man who treasures his family and embraces the simple joys of fatherhood. The event offered a rare window into his personal life—a life filled with laughter, love, and the occasional whimsical appearance by a beloved bear.

As the official birthday for Gutfeld’s youngest child approaches, fans eagerly await what surprises the family might unveil next. But for now, the early celebration stands as a reminder that beyond the late-night jokes and political commentary, Greg Gutfeld is first and foremost a devoted husband and proud father.

Final Thoughts

Greg Gutfeld’s second baby’s early birthday party was more than just a gathering—it was a heartfelt celebration of family, friendship, and joy. With the full The Five cast present and Paddington Bear making a surprise appearance, it was a day that no one who attended—or saw the photos—will soon forget.

In a media landscape often dominated by conflict and division, this intimate moment of connection reminds us all of the simple power of love, laughter, and family. And if this is the softer side of Greg Gutfeld, fans everywhere might just be hoping for a lot more moments like this in the future.