Chelsea Handler, the outspoken comedian and former host of Chelsea Lately, has always been known for her bold personality and unfiltered honesty. In her upcoming book, I’ll Have What She’s Having, Handler shares a surprising and candid story about her brief but intriguing encounter with former New York Governor Andrew Cuomo. In a recent interview with Page Six, Handler revealed that she once had a crush on Cuomo and even planned to take their flirtation to the next level—only to be “ghosted” by him before things could get serious. She jokingly referred to the situation as “dodging a bullet,” suggesting that she feels lucky to have avoided what could have been a complicated or regrettable situation. Handler, who is no stranger to speaking her mind, reflected on how this experience was just one of many instances in her life where she’s managed to sidestep potential trouble, a pattern her sister has even pointed out to her.
The story begins during the COVID-19 pandemic, when Cuomo was gaining widespread attention for his daily updates on the virus. Handler, like many others, found herself drawn to his leadership and presence during that time. She even developed a crush on him, which she didn’t hesitate to express publicly. In 2020, during an appearance on The View via Zoom, Handler made a cheeky comment about wanting to be “penetrated by the governor,” a bold declaration that sparked both laughter and raised eyebrows from the audience. Surprisingly, her words caught Cuomo’s attention, and just three days later, she received a call from an unknown number. It was Cuomo himself, leaving a lengthy message that seemed to open the door to further communication.
Handler was thrilled at the time, even excitedly telling a friend, “I’m going to f–k the governor!” She began planning a trip to New York, presumably with the intention of taking their flirtation to the next level. However, things took an unexpected turn when Cuomo suddenly stopped responding to her texts as soon as she arrived on the East Coast. Despite her initial disappointment, Handler didn’t let the ghosting bring her down. Instead, she continued to embrace her playful and carefree personality, even sending Cuomo risqué photos of herself—such as swimming topless while wearing a face mask and smoking a joint topless. It was her way of keeping the energy light and humorous, even as it became clear that things weren’t going to progress romantically.
In hindsight, Handler reflects on the situation with a mix of humor and self-awareness. She writes in her book that if she hadn’t been so forward about her intentions, she might have ended up in a much more compromising position with Cuomo. Instead, she suggests that he seemed to prefer pursuing women who weren’t directly expressing interest in him—a behavior that took on a darker connotation when Cuomo later faced accusations of inappropriate conduct and sexual misconduct from nearly a dozen women. Handler’s story, while lighthearted on the surface, also touches on the broader context of power dynamics and the complexities of human behavior, especially in the wake of the #MeToo movement.
Handler’s ability to laugh at the situation and move on with ease is a testament to her resilience and sense of humor. She has never shied away from sharing her personal experiences, whether they’re embarrassing, humorous, or deeply vulnerable. In I’ll Have What She’s Having, she continues this tradition, offering readers a glimpse into her life that is both entertaining and thought-provoking. As she prepares for the release of her new stand-up comedy special on Netflix, Handler remains unapologetically herself, proving once again that she can find humor and growth in even the most unexpected moments.
In the end, Handler’s story about her brief encounter with Andrew Cuomo serves as a reminder of her fearlessness and ability to navigate life’s ups and downs with humor and grace. While she may have “dodged a bullet” in this particular instance, her willingness to share the experience highlights her commitment to transparency and self-reflection. Whether she’s talking about politics, sex, or life’s absurdities, Handler continues to be a voice of raw honesty and unapologetic humor, inspiring her fans to embrace their own imperfections and find laughter in the chaos. Her story is a powerful reminder that life is full of unexpected twists and turns—and sometimes, what seems like a missed opportunity can actually be a blessing in disguise.
