Chelsea Handler Reflects on Her Short but Sweet Romance With 50 Cent

Walter Sena
By
Chelsea Handler Reflects on Her Short but Sweet Romance With 50 Cent
Chelsea Handler
Chelsea Handler is getting candid about her brief romance with rapper and entertainment mogul 50 Cent. In a new episode of House Guest with Scott Evans, the comedian opened up about their early 2010s relationship, sharing never-before-heard details about how it started, what he was really like behind closed doors and why the pairing sparked unexpected backlash.

Chelsea Handler revealed that their connection began after 50 Cent appeared as a guest on her former late-night talk show, Chelsea Lately. Just days after the interview, she walked into her office to find it filled with dozens and dozens of roses. Her assistant announced that Curtis Cent had called multiple times, leading Chelsea Handler to ask, “Who’s Curtis?” before learning it was 50 Cent, whom her assistant amusingly referred to as Fiddy.

According to Handler, the rapper’s demeanor surprised her from the very beginning. “He was sweet ’cause he seemed gangsta, but he wasn’t a gangsta,” she said. “The fact that he was shot so many times, you’re like, ‘How did you get shot? That doesn’t even make sense.’”


Chelsea Handler recalled that she was scheduled to perform in New Orleans around the time they started talking and casually mentioned the trip to 50 Cent. To her shock, he accepted her invitation to join her. “He comes to the hotel, he checks in and my assistant goes, ‘Okay, now you’re really going to deal with him,’” she joked. “I was like, ‘Oh sht, what did I get myself into?’”she said.

Despite 50 Cent’s assurance that taking a walk together might draw too much attention, given his massive fan base, Chelsea Handler pushed for it. She remembered people instantly recognizing him, calling him a major deal.

Even with the fame surrounding him, she described the rapper as thoughtful, affectionate and unexpectedly wholesome.

While their relationship didn’t last long, Chelsea Handler said it certainly made waves. She recalled facing significant public criticism, much of which she believes was rooted in racism. “I don’t allow myself to get upset about things like that, But at that point in my career, the backlash was just kind of racist.” Chelsea Handler said. 

Still, she looks back on the experience with fondness, describing 50 Cent as one of the sweetest people she has ever dated.


Source: HotNewHipHop

Comments

MORE FROM
music

More From 3Music News

Coco Blasian Discusses Her Interracial Identity
music | entertainment | fashion & lifestyle | culture | BY Christabel Newman | April 1st, 2026

Coco Blasian Discusses Her Interracial Identity

Born and raised in Japan, Coco moved to Ghana at the age of six, spending part of her early childhood there before returning to Japan. She describes her life as one lived across two worlds, where she is often seen as a foreigner in both cultures...

Vanessa Gyan Urges Women To Choose Happiness, Independence And Self-Worth
entertainment | fashion & lifestyle | culture | BY Christabel Newman | April 1st, 2026

Vanessa Gyan Urges Women To Choose Happiness, Independence And Self-Worth

“We pour so much into other people,” she said. “But you have to pour into yourself first.” For Vanessa, self-care can be as simple as taking time out, looking good and feeling good…

What Really Causes A Runny Tummy, Dr Christian Aminarh Breaks It Down
entertainment | fashion & lifestyle | culture | BY Christabel Newman | March 31st, 2026

What Really Causes A Runny Tummy, Dr Christian Aminarh Breaks It Down

normal bowel habits differ from person to person: some people go once daily, others go once every two to three days but both can be completely normal depending on diet and metabolism...

Mariam K.A. Buahin On Mentorship, Impact And Authentic Leadership
music | entertainment | fashion & lifestyle | culture | BY Christabel Newman | March 31st, 2026

Mariam K.A. Buahin On Mentorship, Impact And Authentic Leadership

At the 6th edition of the 3Media Women’s Brunch, marketing and corporate leader Mariam Kaleem Agyeman-Buahin delivered a deeply reflective and inspiring message on mentorship, impact and the power of sharing one’s journey...

GFA Parts Ways With Otto Addo Ahead Of Crucial World Cup Phase
entertainment | sports | BY Christabel Newman | March 31st, 2026

GFA Parts Ways With Otto Addo Ahead Of Crucial World Cup Phase

The Ghana Football Association has officially announced its decision to part ways with Black Stars head coach Otto Addo, bringing an abrupt end to his tenure with the national team...

Selina Beb Chose Passion Over Profession
entertainment | fashion & lifestyle | culture | BY Christabel Newman | March 31st, 2026

Selina Beb Chose Passion Over Profession

Selina Beb proudly shared that her designs have been featured on major international platforms including BBC, CNN and VOA.

Efia Shemona On Identity And The Miss Ghana UK Journey
entertainment | fashion & lifestyle | culture | BY Christabel Newman | March 31st, 2026

Efia Shemona On Identity And The Miss Ghana UK Journey

“You’ve been smiling for hours,” she shared. “Even when your name isn’t called, you still have to hold that poise.” It’s a test not just of beauty, but of discipline, emotional intelligence and resilience

Baruwa Makes Waves with Viral Single Too Sweet Ashaiman-Lebanon
music | entertainment | fashion & lifestyle | culture | BY Aimee Cherry Quartey | March 30th, 2026

Baruwa Makes Waves with Viral Single Too Sweet Ashaiman-Lebanon

Ashaiman-based rising artiste Baruwa is gaining serious traction in the Ghanaian music scene with his buzzing single Too Sweet (Ashaiman-Lebanon), featuring Baamuji

Juliet Asantewaa Asante On Embracing Every Phase Of Womanhood
music | entertainment | fashion & lifestyle | sports | BY Christabel Newman | March 30th, 2026

Juliet Asantewaa Asante On Embracing Every Phase Of Womanhood

In a relatable moment, she shared her own experience of reinvention, revealing that she is currently raising her adopted daughter, who is still in school...

Kokui Selormey Hanson Calls For Urgent Shift In Women’s Wellness Conversations
music | entertainment | fashion & lifestyle | culture | BY Christabel Newman | March 30th, 2026

Kokui Selormey Hanson Calls For Urgent Shift In Women’s Wellness Conversations

“A lot of women are suffering in silence,” she stated, emphasizing that the current medical landscape is not always equipped with the empathy required to fully support women through their health journeys...

3Media Networks Gathers Powerful Women Under One Roof
music | entertainment | fashion & lifestyle | BY Christabel Newman | March 30th, 2026

3Media Networks Gathers Powerful Women Under One Roof

Held in commemoration of International Women’s Day, the event once again brought together women from diverse industries across Ghana and beyond for a powerful day of storytelling, empowerment and connection...

Moliy Wins Big at the IHEARTRADIO MUSIC AWARDS
entertainment | fashion & lifestyle | culture | BY Christabel Newman | March 27th, 2026

Moliy Wins Big at the IHEARTRADIO MUSIC AWARDS

This win at the iHeartRadio Music Awards further cements Moliy’s position as one of the continent’s most exciting exports...

More Similar Videos

Showboy Shares His Journey From Prison To Becoming Ghana's Biggest Trapper
music,entertainment | Lerny Lomotey | October 27th, 2025

Showboy Shares His Journey From Prison To Becoming Ghana's Biggest Trapper