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Bridget Hall

He and the former Victoria’s Secret model supposedly had a fling back in 1994, in which some consider Bridget to be his first “model girlfriend.”

However, Bridget later admitted that “nothing happened” between the two of them, and it appears there’s no hard feelings on either end.

Brittany Daniel

Although it was never confirmed, he and his Basketball Diaries co-star were rumored to have gotten together in 1994 after filming had wrapped.

Naomi Campbell

The pair are not only close “photobombing friends,” but they also hooked up in 1995, and decided to keep things platonic shortly afterward.

Kristen Zang

He and Kristen’s on and off relationship lasted from 1995 to 1999, and despite his criticized love life, she spoke highly of him in an essay she wrote for People in 2022.

“I visited Leo for long periods of time on various sets in different countries. I loved his friends and he loved mine. We were like one big happy family.”

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