![]() Many of their fans had super heart eyes for Usher and Chilli's relationship. ![]() ![]() Usher and Chilli first met in 1993 when Usher first signed his deal at the age of 14, and Chilli was 21 at the time, as Zimbioreported. Those ages sound unsettling at first, but the former R&B duo wouldn't begin dating until 2001, eight years later. Fortunately, we have the "U Remind Me" video to thank for being the reason these two ended up together - however, this was not the first time they met. With the TLC singer hanging on Usher's shoulder, the couple were Hollywood's "it" couple of the early 2000s. ![]() Step aside, Justin Timberlake and Britney Spears! The former popstar couple and their matching ensembles had nothing on singers Usher and Rozonda "Chilli" Thomas' relationship.
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