Back in 1994, rumor had it that Leo and model Bridget Hall were an item, although the two denied it. According to a 1998 article by The London Sun, DiCaprio and Hall were intimate before the actor “dumped her like a hot potato,” and although the site said Hall called her time with DiCaprio “disappointing,” the model told New York Magazine, “Nothing happened.”

That same year, DiCaprio reportedly dated his co-star from “The Basketball Diaries,” Brittany Daniel. Daniel’s relationship with DiCaprio didn’t last long and the actress went on to star in films like “White Chicks” and TV shows like “Sweet Valley High.” However, Daniel took a break from acting in 2011, when she was diagnosed with non-Hodgkin’s lymphoma.

Back in 1995, DiCaprio was just beginning his trend of dating supermodels, starting with ‘90s icon Naomi Campbell. Although the relationship between the two didn’t last long, it ended up blossoming into a lifelong friendship. In 2015, the two were photographed at Jason Statham’s home, and in 2022, the two were spotted in attendance at a wedding.

DiCaprio and actor Kristen Zang began dating in 1995, and their relationship lasted for four years. Even now, Zang remains loyal to DiCaprio, defending him against the "ageist" label, and saying “Leo was a very sweet and thoughtful boyfriend […] after my 25th birthday (ha, I know what you’re thinking) it was over for good […] [because] I had outgrown that version of myself.”

In the late ‘90s, Leo set his sights on supermodel Amber Valletta, and after his people got in touch with her people, the two started dating. Although their relationship didn’t stand the test of time, Valletta didn’t stop believing in love, and she shared that love remains a top priority, saying, “Love is essentially all we really are — we are created from it.”