50 Cent, whose real name is Curtis Jackson, left the "Chelsea Lately" host a flirtatious voicemail after appearing on her show, and even reportedly sent her flowers.
The rapper, also 35, has a 13-year-old son, Marquise, from a previous relationship.
Photos of 50 and Chelsea chatting at New Orleans' Blue Nile jazz bar were posted on TMZ on Monday (October 4).
In addition to spending face time with Handler, the rapper also took the stage and did a little freestyle for the crowd.
“He was just so romantic and kind and very old-fashioned, and I wish I knew then how to treat a man like that.” READ Speaking Truth To ‘Power’: 50 Cent & Co.
Define Their Character Flaws And 48 Laws In the nearly 14 years since their break-up, Fox and Fifty have exchanged friendly fire on social media many times.
Throughout the early 2000s Ciara released a slew of hits and had built a reputation for being an energetic entertainer.