Honestly, if you were scrolling through Twitter in 2010 and saw a grainy photo of 50 Cent and Chelsea Handler getting cozy at a bar in New Orleans, you probably thought it was a fever dream or a very strange prank. It was the ultimate "odd couple" moment of the decade.
He was the guy who survived nine shots and built a rap empire on a "get rich or die tryin'" mantra. She was the sharp-tongued queen of late-night E! television who made a career out of mocking celebrities. It didn't make sense. And yet, for a few chaotic months, 50 cent dating chelsea handler was the only thing anyone in Hollywood wanted to talk about.
They were everywhere. One minute they’re at a dinner in Malibu, the next they’re posting selfies from a bed. But like most high-octane celebrity flings, the wheels came off fast.
The Lamborghini and the Chocolate Bentley
People always ask how it even started. It wasn't some grand red carpet meeting. Curtis Jackson (that's Fiddy’s real name, obviously) was a guest on Chelsea Lately. He was charming. He flirted. She flirted back. Then, the flowers started arriving.
Chelsea recently spilled some new tea on the Call Her Daddy podcast in early 2025, and it turns out 50 was quite the romantic. He flooded her office with dozens of roses. Her assistant kept telling her, "Curtis Cent called again." Chelsea’s response? "Who the hell is Curtis?"
Once they actually started hanging out, the wealth gap—or rather, the display of wealth—got weirdly competitive. Chelsea recalls 50 showing up to her house in a different supercar every night. One day it was a Lamborghini, the next a yellow Ferrari.
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"I realized he was borrowing all these cars from different dealerships," Handler joked. "I didn't know you could do that as a celebrity."
Naturally, in typical Chelsea fashion, she didn't want to be outdone. She went out and bought a "chocolate Bentley" just to prove a point. She ended up stuck with that car for two years after they broke up, driving around feeling like, in her words, a "dumb b----" trying to look like a rapper.
Why it Ended: The Infamous Three-Way Call
You’d think a relationship between two moguls would end over something huge, like a business deal gone wrong. Nope. It ended because of a "juvenile" phone call involving another famous singer.
While they were dating, 50 Cent’s ex-girlfriend—rumored to be Ciara—was scheduled to appear on Chelsea’s talk show. 50, trying to be... helpful? protective? messy?... decided to call Chelsea to "warn" her. He told her the ex still had feelings for him and wanted him back.
Chelsea wasn't having it. She was at work, trying to run a show, and her boyfriend was calling to talk about high school-level drama.
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- 50 tried to set up a three-way call to "prove" what was happening.
- Chelsea told him he was acting like an "eighth grader."
- She called him a "street person" (a comment she later admitted was pretty offensive).
- She hung up and literally never spoke to him again for years.
It was a sharp, cold ending to a romance that had Jennifer Aniston and Reese Witherspoon texting Chelsea every day for updates. Her famous friends were obsessed with it. They thought it was the funniest thing that had ever happened to her.
The Sobriety Disappointment
One of the funniest misconceptions about 50 Cent is the "party" lifestyle. Because of the music videos, everyone assumes he’s constantly pouring out bottles of expensive vodka.
Chelsea recently revealed on the House Guest podcast that the "biggest disappointment" of dating him was his sobriety. He doesn't do drugs. He barely drinks. For a woman who has built a brand on being the life of the party with a drink in her hand, finding out the "gangster" rapper was the responsible one was a bit of a buzzkill.
He was, as she puts it, "a big fat teddy bear." He was sweet, he was polite, and he was the "complete antithesis" of his public image.
Where They Stand in 2026
Despite the messy breakup, these two have developed a weirdly sweet "exes" friendship over the last decade. They needle each other on Instagram constantly. When 50 Cent briefly suggested he might support Donald Trump in 2020, Chelsea publicly reminded him that he was "a Black person" and offered to pay his taxes if he changed his mind.
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He loved it. He responded with "Look at my ex-girlfriend, she’s crazy."
As of early 2026, Chelsea says they still DM. She’s even joked in her recent comedy special, The Feeling, that 50 is the only ex-boyfriend people still ask her about in every single interview. There’s a certain respect there. They both know how to play the fame game, and they both know how to keep people talking.
What We Can Learn from the Chaos
If you're looking for a takeaway from the saga of 50 cent dating chelsea handler, it's probably this:
- Opposites attract, but values keep you together. They had great chemistry, but his "juvenile" approach to relationship drama didn't mesh with her "boss" mentality at work.
- Don't buy a Bentley as a joke. You'll be paying the insurance on it long after the guy is gone.
- Keep things cordial. Being able to laugh about a two-month fling fifteen years later is a much better look than holding a grudge.
If you want to see the sparks for yourself, go back and watch the 2010 interview on Chelsea Lately. The body language says everything the publicists tried to hide for months.
Actionable Insight: If you're going through a breakup or dealing with an ex, take a page out of the Handler-Jackson playbook. Address the drama directly, apologize for the "heated" comments if you need to, and eventually, try to get to a place where you can joke about the "chocolate Bentley" moments of your own life. Turning a failed romance into a decade of mutual respect (and good PR) is the ultimate power move.