Chelsea Handler, the comedian and former host of 'Chelsea Lately,' has been candid about her dating history, which includes high-profile figures like rapper 50 Cent and celebrity chef Bobby Flay. In a May 2026 podcast episode, Handler clarified her stance on relationships, asserting she is not a commitment-phobe but prefers to end things before they become too serious. Her longest romance was with Ted Harbert, lasting four years, which ended due to differing expectations and a notable incident involving a threesome that she discussed in detail. Handler referred to her two-month fling with 50 Cent as 'toxic,' despite initially calling him her 'favorite ex,' and shared how the relationship was exhausting due to the distance. Additionally, she criticized Bobby Flay for a disappointing date where he left her with the bill after room service. Handler also teased about a 'nice little affair' with another mystery actor while maintaining a level of privacy about her current romantic interests.