1997: Amber Valletta

Amber Valletta was another one of Leo’s supermodel crushes. The story goes that Leo spotted her in a magazine, asked someone to track her down, and they briefly dated. Neither of them confirmed the romance publicly, but the story has lived on as a classic Leo move.

1997: Helena Christensen

That same year, Leo was also linked to Danish model Helena Christensen. Like Amber, their supposed relationship was more rumor than fact, fueled by the limited tabloid culture of the late ’90s. With little evidence to back it up, this one goes down in history as more speculation than romance.

1998: Eva Herzigová

These two met at the premiere of The Man in the Iron Mask and apparently the connection was almost instant. Eva publicly spoke about DiCaproio,  said Leo was a kind man, full of energy, and no to subtly hinted at a memorable first night together. It didn’t last long, but Eva’s rare public comments made this fling more than just a whisper.