5 Shocking Details Chelsea Handler Just Revealed About Dating 50 Cent: The Untold Story Of An Unlikely Couple

The unlikely, brief, and yet perpetually fascinating romance between stand-up comedian Chelsea Handler and hip-hop mogul 50 Cent (Curtis Jackson) remains one of the most talked-about celebrity pairings of the early 2010s. Despite dating for only a short period, their connection has generated endless public curiosity. As of late December 2025, the story is back in the spotlight, not because they’ve reunited, but because Handler has offered a series of candid, hilarious, and surprisingly sweet recollections about the rapper, shedding new light on their dynamic, the public's reaction, and the current status of their enduring friendship.

These recent interviews, years after their split, confirm that the bond between the outspoken late-night host and the powerful G-Unit founder was far deeper and more genuine than many initially believed. From the rapper's unexpected charm to the unfortunate "racist" backlash the couple faced, Handler’s fresh perspective provides a definitive, updated look at why their relationship was so unique and why they remain on friendly terms today.

A Tale of Two Icons: The Chelsea Handler & 50 Cent Biography

Before delving into the details of their unexpected romance, it is essential to understand the distinct worlds from which these two cultural powerhouses emerged. They are figures who, despite their different industries, share a common thread of fierce independence and an unapologetic public persona.

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Chelsea Handler: The Unfiltered Comedic Force

• Full Name: Chelsea Joy Handler
• Born: February 25, 1975, in Livingston, New Jersey
• Career Highlights: Stand-up comedian, actress, writer, television host, and producer.
• Major Works: Host of the E! late-night talk show Chelsea Lately (2007–2014); host of the Netflix talk show Chelsea (2016–2017); author of several best-selling books including My Horizontal Life and Are You There, Vodka? It’s Me, Chelsea.
• Public Persona: Known for her provocative, unfiltered, and often self-deprecating humor, and her candid approach to relationships and politics.

50 Cent: The G-Unit Mogul and Media Titan

• Full Name: Curtis James Jackson III
• Born: July 6, 1975, in South Jamaica, Queens, New York
• Career Highlights: Rapper, actor, producer, and entrepreneur.
• Major Works: Multi-platinum debut album Get Rich or Die Tryin’ (2003); founder of the record label G-Unit Records; executive producer of the successful Starz television crime drama series Power and its various spin-offs.
• Public Persona: Famous for his streetwise background, rags-to-riches story, sharp business acumen, and notorious social media trolling.

The Unlikely Romance: How a Rapper Convinced a Comedian

The story of Chelsea Handler and 50 Cent’s relationship began not in a dimly lit club or a private party, but on a brightly lit television set. Their initial connection was a testament to the fact that opposites often attract, especially when both parties are confident and successful in their own right.

The Meeting on Chelsea Lately

The pair first met when 50 Cent appeared as a guest on Handler’s popular E! network talk show, Chelsea Lately. The chemistry was immediately noticeable to viewers, a playful and unexpected banter between the sarcastic host and the charismatic rapper. Handler has since recounted that 50 Cent was incredibly persistent, essentially "convincing" her to go out with him.

The Brief, Headline-Grabbing Relationship

Their romance officially took off around 2010 and lasted briefly into 2011. The pairing of a white, outspoken female comedian with a Black, mega-successful hip-hop artist was an instant media sensation, dominating tabloids and social media discussions. They were frequently seen together, and Handler, true to form, often joked about the relationship on her show, which only fueled the public's fascination.

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Handler revealed that the breakup itself was somewhat "juvenile," stemming from an incident where one of 50 Cent’s former girlfriends appeared on her show. Despite the short duration and odd ending, the relationship clearly left a lasting, positive impression on Handler.

Sweetness, Sobriety, and 'Racist' Backlash: Handler's Fresh Revelations

In recent appearances on various platforms, including the Call Her Daddy podcast and Scott Evans' House Guest podcast, Chelsea Handler has offered a surprisingly warm and detailed look back at her time with Curtis Jackson, contrasting sharply with her usual sharp-tongued humor.

The "Sweet Guy" and Favorite Ex

Contrary to the tough, street-smart image 50 Cent cultivated in his music and business ventures, Handler consistently describes him as one of the "sweetest people" she has ever dated. She has repeatedly called him her "favorite ex-boyfriend," emphasizing that he was "fun to be around" and that her friends loved hanging out with him. This description of the G-Unit mogul as a genuinely kind and charming individual is a key entity that adds depth to the narrative of their relationship.

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The Shocking Joke About Sobriety

Perhaps the most talked-about recent revelation is Handler’s candid, yet clearly joking, comment about 50 Cent’s lifestyle. Handler, who has been open about enjoying alcohol, stated that her "biggest disappointment" in dating him was that he is sober. “He doesn’t do drugs, which was the biggest disappointment,” she quipped, highlighting the contrast in their personal habits but also the lighthearted nature of their connection. This self-deprecating humor further cemented the public understanding of their bizarre but affectionate dynamic.

Addressing the Public Reaction and 'Racist' Comments

A more serious entity Handler addressed was the intense public scrutiny and the nature of the backlash they faced as an interracial couple. She recalled the commentary surrounding their romance as being "just kind of racist". This acknowledgement highlights a darker side of the media coverage at the time, where the focus was often on the perceived racial incongruity of the pairing rather than the genuine connection between the two individuals. Handler’s willingness to address the "racist backlash" head-on adds a layer of social commentary to the story.

The Current Status: Friendly DMs and Mutual Respect

Years after their highly-publicized split, the relationship between Chelsea Handler and 50 Cent is defined by mutual respect, playful banter, and a lasting friendship. There is no indication they have reconciled romantically, especially given Handler's recent high-profile relationship with comedian Jo Koy, but their friendly interactions continue to make headlines.

50 Cent’s Recent Reactions

50 Cent, known for his quick wit and social media engagement, has not shied away from reacting to Handler's recent comments. When Handler made an NSFW mention of him in a stand-up routine, the rapper reacted publicly, showing that the playful energy between them is still very much alive. He has also commented on Handler's recent interviews, including one where she discussed buying him a "Chocolate Bentley" for Christmas, proving he pays attention to her public mentions of him.

The Lasting Legacy of a Bizarre Pairing

The story of Chelsea Handler and Curtis Jackson is a powerful example of how two individuals from vastly different professional worlds—Hollywood comedy and hardcore hip-hop—can find a genuine connection. Their brief relationship, which began after his appearance on her late-night talk show, continues to be a source of amusement and curiosity because it defied expectations. They proved that beyond the celebrity personas of the stand-up comedian and the G-Unit founder, there was a simple, sweet connection that has evolved into an enduring, if unconventional, friendship.

The candidness of Handler's recent reflections, calling him her favorite ex and detailing his surprising "sweet" nature, has solidified the narrative. Their story is less about a failed romance and more about a successful, lasting friendship built on mutual respect and an ability to laugh at the absurdity of their own celebrity.