Chelsea Handler Reveals Surprising Details About Dating 50 Cent

American comedian and author Chelsea Handler recently shared candid insights into her brief romance with rapper 50 Cent, also known as Curtis James Jackson. The two dated for a short period in 2011 after 50 Cent appeared as a guest on Handler’s talk show.

During an appearance on the podcast “House Guest with Scott Evans,” Handler recounted how 50 Cent made a strong impression on her. Following his guest spot, Handler returned to her office to discover “dozens and dozens of roses” waiting for her, a gesture that caught her off guard.

Unexpected Attention from a Rap Icon

Handler’s assistant informed her that 50 Cent had called multiple times, leading to a moment of confusion. “I was like, ‘Who is Curtis Cent?’” she recalled, only to have her assistant clarify that it was the rapper, affectionately known as “Fiddy.” Despite her initial hesitation to return his calls, Handler noted that 50 Cent’s approach felt different from typical romantic advances.

“He was sweet because he seemed gangster, but he wasn’t a gangster,” Handler said, reflecting on his multifaceted personality. She mentioned being intrigued by his background, particularly given that he had survived multiple gunshot wounds, which prompted her to wonder, “How did you get shot?”

A Memorable Encounter in New Orleans

The pair eventually met face-to-face in New Orleans, where Handler was performing. During their time together, Handler suggested they go for a walk. However, 50 Cent was reluctant, stating he “can’t really go for a walk outside.” Handler playfully pushed back, saying, “I think you can. Get over yourself.”

As they strolled through the streets, Handler was surprised by the recognition 50 Cent received. “Every person we saw was like, ‘50 Cent!’ I didn’t get it,” she admitted, highlighting the rapper’s celebrity status and the warm reception he garnered in the city.

Handler’s reflections on her time with 50 Cent reveal a unique glimpse into a relationship that intrigued many. The encounter illustrates not only the unexpected connections that can form in the world of entertainment but also the surprising personalities behind public personas.