Chelsea Handler is making headlines once again, thanks to the buzz surrounding Netflix’s The Roast of Kevin Hart, which premiered on May 10, 2026. This resurgence in popularity has reignited discussions about her past romance with rapper 50 Cent, reminding fans of her colorful dating history and the intriguing relationships that have shaped her personal life.
Handler, a familiar face in television since 2001, has appeared in various shows, including The Good Wife, My Wife and Kids, and Will & Grace. However, her romantic escapades have often drawn as much attention as her professional achievements. Let’s take a closer look at Chelsea’s journey through love and heartbreak.
Her first high-profile relationship was with Ted Harbert, the former chairman of NBC, which began in 2006. At the time, Harbert was president of E! Entertainment, the network that aired Handler’s hit show, Chelsea Lately. Unfortunately, their romance ended in 2010, and Handler later revealed that their work connection contributed to their split. In a 2012 interview with Marie Claire, she recounted how returning home to discuss work was exhausting. Fast forward to 2023, Handler opened up about her past, mentioning an alleged threesome during their relationship, but quickly clarified on The Tonight Show Starring Jimmy Fallon that this was not the reason for their breakup.
Handler’s brief fling with 50 Cent in 2011 also raised eyebrows. The two were linked romantically for about two months, with Handler admitting to Us Weekly that she struggled to navigate their relationship. During a 2013 chat with Oprah Winfrey, she affectionately referred to him as a “sweetheart” but noted the relationship was never serious. Handler humorously recalled her hesitation to date someone with a name like “50 Cent.”
Following her time with the rapper, Handler entered a relationship with businessman Andre Balazs, but it was a tumultuous experience. In 2012, she described their romance as draining, citing the challenges of long-distance dating and the toll it took on her career. Their relationship ended the same year, leaving Handler to reflect on the emotional impact it had on her.
In 2021, Handler found love again with comedian Jo Koy, with whom she had shared a long-standing friendship. Their relationship blossomed, and Handler frequently showcased their connection on social media. However, by 2022, the couple parted ways. During an appearance on Brooke Shields’ podcast, Handler explained that they struggled to align on several important issues, leading her to feel like she was compromising her own identity.
Now, Handler is reportedly in a new relationship, but she’s chosen to keep her partner out of the public eye. In a March 2026 interview with the Las Vegas Review-Journal, she recounted their first meeting at The Cosmopolitan hotel in Las Vegas, where a playful encounter at a blackjack table sparked their connection. Handler humorously shared that she borrowed $1,000 from him, which she promptly returned after a winning streak.
Her new beau has already joined her on adventures, including a vacation in Antarctica and a birthday celebration in Finland. As Handler navigates this new chapter, fans are left wondering who this mystery man is and what the future holds for the beloved comedian.
What do you think of Chelsea Handler’s romantic journey and her decision to keep her current relationship private? Share your thoughts!
