Popsugar Celebrity And Entertainment Leonardo Dicaprio All the Women Leonardo DiCaprio Has Dated A Not-So-Brief History of All the Ladies Leonardo DiCaprio Has Dated 24 April, 2016 by Britt Stephens 5 Shares View On One Page Photo 5 of 18 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 5 Natasha Henstridge Leo was reported to have "had a fling" with Species star Natasha Henstridge in 1997. Previous Next Start Slideshow Leonardo DiCaprioCelebrity FactsCelebrity Couples