#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.

By Isabel Jones
Nov 08, 2018 @ 2:45 pm

Who: Oscar-winning actor Leonardo DiCaprio, 43, and Brazilian model Gisele Bündchen, 38.

How they met: It’s rumored that DiCaprio saw Bündchen walk at a runway show around 1999 and sought her out, which sounds about right. (As evidenced by Leo’s long and somewhat predictable dating history, the Titanic star has no problem meeting models.)

When they peaked: Lucky Gisele, who not only has the good fortune of being tall, beautiful, and worth a literal fortune, also made history as the only woman (who did not carry Leo in her womb) to accompany the ladies’ man to the Oscars, a title she carries to this day.

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Why we loved them: Leo’s relationship with Gisele marks an important moment in his relationship history — she was, basically, the last age-appropriate woman he ever dated.

After Gisele, he moved onto a slew of barely legal models that included 20-year-old Bar Refaeli (when he was 31), 23-year-old Anne Vyalitsyna (when he was 35), 23-year-old Madalina Ghenea (when he was 37), 23-year-old Erin Heatherton (when he was 38), 21-year-old Toni Garrn (when he was 39), 25-year-old Kelly Rohrback (when he was 41), 24-year-old Nina Agdal (when he was 42), and his current paramour, 21-year-old Camila Morrone (Leo turns 44 on Sunday). All that considered, the actor says he had “better success meeting girls before Titanic,” so go figure …

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The breakup:

The pair split briefly in 2002, reportedly because Gisele was “a bit bored” with her personal king of the world. "They haven't had a big argument or anything like that," a source told The Telegraph. "It's just that Gisele was getting a bit bored and wanted to move on."

They reunited shortly after, though — maybe Leo got less boring? — until calling it quits for good in 2005. Gisele moved to L.A. for Leo, “the first love of my life,” but decided to return to New York in 2004. Two of her horses and three of her dogs stayed behind with the actor — one of which was with DiCaprio post-split, until at least 2009.

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It was during Gisele’s relationship with Leo, around 2003, that she began to suffer from panic attacks and suicidal thoughts. "I had been smoking cigarettes, drinking a bottle of wine and three mocha Frappucinos every day, and I gave up everything in one day," the model told People. "I thought, if this stuff is in any way the cause of this pain in my life, it's gotta go." Another lifestyle choice that didn’t make the cut? Leo.

Feeling “alone” in her new life’s journey, the pair amicably split. “Everyone who crosses our path is a teacher, they come into our lives to show us something about ourselves,” she explained. “And I think that’s what he was. What is good versus bad? I honor him for what he was.”

Years prior, Gisele called her ex “a really wonderful person,” and explained that she respected him and his environmental work. “We know what we had; we were very young, and we grew together in a lot of ways. We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best,” she said.

RELATED: Nicole Kidman Reveals Why She and Lenny Kravitz Called Off Their Engagement

Where they are now:

Four years after splitting from Leo, Gisele wed NFL quarterback Tom Brady. They welcomed their son, Benjamin, that same year, and their daughter, Vivian, three years later in 2012.

Bündchen was the world’s highest paid model from 2002 until 2017, when she was eclipsed by Kendall Jenner. Like DiCaprio, she’s also an avid philanthropist and activist. Gisele’s been a UN goodwill ambassador since 2009 and joined the Rainforest Alliance board of directors in 2014.

As mentioned above, DiCaprio’s led quite the prolific dating life since splitting from Bündchen in 2005.

Professionally, Leo’s also thrived. The actor won his long-awaited first Oscar in 2016 with his performance in The Revenant. DiCaprio has several big name productions ahead of him, including a role in Quentin Tarantino’s Manson murders film Once Upon a Time in Hollywood, police drama The Black Hand, Martin Scorsese’s adaptation of Killers of the Flower Moon, and a Scorsese biopic about Theodore Roosevelt.

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First look. #OnceUponATimeInHollywood

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