Leonardo DiCaprio’s dating life has been a hot topic for years, with several Victoria’s Secret Angels in his dating history.

Leonardo DiCaprio was once found “paging through a Victoria’s Secret catalog” on the set of the 2006 movie, according to Blood Diamond director, Edward Zwick, and the joke was made that the actor was “shopping” for his next romantic partner. It’s no secret DiCaprio has dated some of the world’s most beautiful women and has been romantically linked to a series of Victoria’s Secret models, including Gisele Bundchen, Gigi Hadid, Bar Refaeli, Eva Herzigova and Helena Christensen,

The filmmaker wrote about DiCaprio’s behavior in his memoir entitled Hits, Flops, and Other Illusions: My Fortysomething Years in Hollywood.

In addition to DiCaprio, Edward Zwick has worked with some of the biggest stars on the planet, including with Tom Cruise in The Last Samurai and helped Denzel Washington win an Academy Award for Glory.

In the following, we take a look at what happened on the set of Blood Diamond that became a joke about Leonardo DiCaprio’s dating life. We also take a look at a couple of Leonardo Dicaprio’s high-profile model relationships.

How Leonardo DiCaprio’s Dating Choices Became A Joke On The Set Of Blood Diamond
Edward Zwick revealed secrets from behind the scenes of the Sierra Leone movie, Blood Diamond, in his recent memoir. He praised the “terrific” Leonard DiCaprio and his two co-stars, Jennifer Connelly and Djimon Hounsou. The political thriller grossed $171 million worldwide and received five Oscar nominations, including Best Actor for DiCaprio and Best Supporting Actor for Hounsou.

The Legends Of The Fall director added that he remembers “only one instance of even the mildest misbehaviour” between the Oscar-nominated trio of actors, adding: “It’s more a testament to their camaraderie than anything else.”

“It seems Leo was currently between gorgeous girlfriends,” Zwick wrote in his book, in a segment that has now gone viral. “One morning I walked into the makeup trailer as I often did to discuss the day’s work with him. I found him in the chair waiting for his turn and noticed he was paging through a Victoria’s Secret catalogue.”

“‘What are you doing?’ I asked. Connelly was in the chair beside him,” Zwick wrote. “Without even looking over, she said, ‘Shopping’.”

Gisele Bündchen Was One Of Leonardo DiCaprio’s Victoria’s Secret Angel Girlfriends

Before supermodel Gisele Bündchen married Tom Brady, she dated Leonard DiCaprio. The former couple dated on and off for six years, from 1999 to 2005. Gisele is one of DiCaprio’s longest and most high profile relationships.

The Brazilian model explained that their breakup came as a result of trying to better herself after struggling with anxiety, panic attacks and suicidal thoughts.“I didn’t feel like I could share my panic attacks with anyone,” she explained to PORTER magazine. “So I’d suppress it, and the more I suppressed it, the bigger it became.”

Gisele also explained in the interview that she considered jumping off a balcony, which led to her surrounding herself with loved ones and trying to have healthier habits. This tough period of her life helped her realize the Inception actor was not right or her, despite her love for him. “Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes.”

Two years following her split from The Wolf Of Wall Street star, Gisele Bündchen started dating football player Tom Brady and married in 2009. They sadly divorced in 2022. The couple share two children, Vivian and Benjamin Brady.

Despite the breakup, Bündchen remained in contact with both DiCaprio and his mother, with the actor even looking after her dog occasionally.

“We know what we had. We were just not meant to be boyfriend and girlfriend, but I respect him enormously.”

Camila Morrone Opened Up About Age Gap With Leonardo DiCaprio

Another high-profile model Leonardo DiCaprio has dated was Camila Morrone. Their relationship hit the headlines, and the almost 25-year age gap caused controversy.

The Daisy Jones and the Six actress wasn’t afraid to speak candidly about it during an interview with The Los Angeles Times. They were first linked in 2017 after the Once Upon A Time In Hollywood actor broke up with model Nina Agdal.

“There’s so many relationships in Hollywood⁠—and in the history of the world⁠—where people have large age gaps. I just think anyone should be able to date who they want to date,” she said, but admits that “I probably would be curious about it too.”

They also became a meme during their relationship after the paparazzi caught DiCaprio taking photos of Corrone on the beach. “I saw the meme,” she explained. “Poor thing, he’s being called an Instagram boyfriend. He’s an environmentalist and a movie star, and it doesn’t mean a thing!”

The pair kept a mostly low profile together, although they did go to the US Open together. The couple broke up in 2022 after five years together. Although neither spoke about it in public, sources told outlets that it was due to Morrone’s rising profile as an actress.

“Leo and Camila have had a few breaks in the past few months. It’s a matter of deciding whether they are in it for the long haul or just going to let it die,” a source told In Touch Weekly. “With all of Leo’s girlfriends, once she became focused on work and had her own priorities, he got distant. Rather than have dramatic breakups, they took time apart.”

A source told E! News said that the celebrity couple had both been “traveling a lot” and “distance played a factor” in their five-year relationship ending. The fact the model turned 25 a few months prior only added to the joke that DiCaprio dumps women when they turn 25.

Speaking to The Cut in a 2023 interview, Camila Morrone revealed that her recent break up had taught her some important life lessons. While she didn’t specify her split with DiCaprio, she explained, “I’ve never learned so much as being 25 years old.”

The former model and Marmalade actress added, “I am just starting to feel like a woman. But I also feel little in a lot of senses.”