Kidada Jones: A Brush with Stardom
In the late 1990s, Leo's presence in photos alongside Kidada Jones, daughter of Quincy Jones, sparked intrigue. While no confirmation of a romance exists, there's a chance that Leo and Kidada shared a brief fling just before Leo's relationship with Gisele Bundchen began.
For Kidada, dating Leo was a footnote in her romantic history, having been previously engaged to rapper Tupac Shakur.