Popsugar Celebrity Celebrity Facts Who Has Leonardo DiCaprio Dated? Leonardo DiCaprio's Dating History, From Naomi Campbell and Gigi Hadid to His Latest Fling 20 October 2023 by Britt Stephens View On One Page Photo 18 of 22 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 18 Natasha Henstridge The actor was reported to have "had a fling" with "Species" star Natasha Henstridge in 1997. Previous Next Start Slideshow Celebrity FactsLeonardo DiCaprioCelebrity Couples