Usher recently tied the knot with his longtime love, Jenn Goicoechea, in a surprise wedding following his electrifying performance at the 2024 Super Bowl. However, in a recent interview, the 45-year-old Grammy-winning artist opened up about another significant moment from his romantic past—a surprising proposal to none other than Chili, the talented TLC performer.
In an exclusive conversation with People, Usher shared the unexpected revelation, shedding light on a chapter from his dating history that left a lasting impact on him. Usher and Chili’s romantic journey took a brief but intense turn, ultimately leading to a proposal that did not go as planned.
Reflecting on his emotions during that time, Usher revealed, “I wanted to marry her. I proposed, and she told me no. I went through a great deal of pain after that, not trusting women or wanting to open up.” This unexpected twist in their relationship, which happened in the early 2000s, brought about a significant shift in Usher’s perspective on love and relationships.
Chili, who had been Usher’s childhood crush, was someone he deeply cared about. However, despite his heartfelt proposal, their relationship faced challenges, and the two eventually parted ways in 2004. Usher confessed that he struggled with the aftermath of the rejection, acknowledging the impact it had on his ability to trust and be vulnerable in future relationships.
Opening up about the dynamics of their connection, Usher explained, “I was a young man, and she had very specific rules that didn’t work for me. We were missing each other. I really did want to have a different type of relationship where she was there with me, and she couldn’t be. She didn’t believe that I was actually in love with her as much as I was.” The complexities of their relationship were rooted in differences that ultimately became insurmountable.
Despite the romantic turbulence, Usher emphasized that there is no lingering animosity between them. “We’ve since become cool with each other, celebrate each other, and it’s always light when we see each other,” he shared. Time has healed the wounds, and both artists have found a way to appreciate and support each other in their respective journeys.
As Usher takes on this new chapter of his life with Jenn Goicoechea, the unexpected proposal to Chili serves as a poignant reminder of the twists and turns in matters of the heart. Love, it seems, has its unique way of shaping our stories, and Usher’s revelation has added another layer of intrigue to his storied romantic history.
