Naomi Campbell (1995)
A tale as old as Hollywood time, the longtime friends reportedly hooked up way back when, but chose to keep things platonic.
Instead, they went on vacations with their respective significant others, attended and supported one another’s charitable events and, of course, photobombed 50 Cent.
Maybe there’s hope for Leo after all.
Kristen Zang (1996-1997)
Imagine accompanying a young Leonardo DiCaprio to the premiere of “Romeo + Juliet”. Sounds cool, right?
The Daily News reported that Kristen dumped a 23-year-old Leo soon after because of his “immaturity” and group of guy friends, saying he needed to “grow up.”
So basically, nothing’s changed.
Helena Christensen (1997)
After his “Titanic” fame, Leo turned his sights on partying with models; the first woman to lead the trend was Helena Christensen, who reportedly hooked up with DiCaprio before her five-year relationship with “The Walking Dead” star Norman Reedus.
Amber Valletta (1998)
Rumour has it that Leo spotted Amber in a magazine and had “his people call her people.”
A fact we’d never take off our CV.
Gisele Bündchen (1999 – 2005)
Meet the only other women (aside from his mom, Irmelin, and constant BFF-we-wish-it-was-more Kate Winslet) to accompany Leonardo DiCaprio on a red carpet (post “Titanic” fame): Gisele Bundchen.
The model also reportedly “called it quits” on their six-year on-again-off-again relationship, telling Vanity Fair in 2009 that there were no hard feelings after their split.
“We were very young, and we grew up together in a lot of ways,” Gisele said. “We were just not meant to be boyfriend and girlfriend, but I respect him enormously and I wish him nothing but the best,” clearly foreshadowing what Leo’s love life would be for the next decade (hopefully not more).
Bundchen found her forever love in NFL star Tom Brady, marrying in 2009.
Bar Refaeli (2005 – 2011, with a short “break” in 2009)
After Gisele, Leo continued his streak of foreign-born Victoria’s Secret models by dating the beautiful Israeli, Bar Refaeli.
Though one of Leo’s longest relationships, Bar has said that she was “very grateful” for the time the pair spent apart in 2009. Leo, however, clearly thought that meant the two were on a “BREAK” (think Ross on “Friends”), reportedly hooking up with model Anne Vyalitsyna after meeting her in Ibiza.
Like the other ladies in the Leo’s Lost Love club, Bar has moved on, marrying Israeli businessman Adi Ezra in 2015 and giving birth to a girl, Liv, in 2016.
Blake Lively (May 2011 – Oct 2011)
Yes, that’s right, the future Mrs. Ryan Reynolds might never have been if her relationship with Leo hadn’t fizzled out.
The couple started rumours when photos of them canoodling at Cannes (on a yacht, of course) went public and fulfilled all our summer love dreams through 2011. From Italy to partying at The Darby in NYC and holding hands in LA, Blake even spent her birthday in Australia while Leo was filming “The Great Gatsby”.
Thankfully (we really couldn’t imagine Blake with anyone but Ryan) the pair called it quits and Blake quickly moved on to “Green Lantern” star and “pal” Ryan Reynolds.
Erin Heatherton (December 2011 – November 2012)
Leo officially moved on after being spotted touring the grounds of Sydney’s historic Vaucluse House.
The woman with him? Erin Heatherton. The relationship? Similar to the others.
Finding herself in the typical places that a relationship with Leonardo DiCaprio takes you (read: the beaches of [insert beautiful tropical place here]), Heatherton was also spotted keeping it low-key with Leo in New York.
This time it was Leo’s reported schedule for “The Wolf of Wall Street” that kept their love from blossoming, with Heatherton later telling the Daily Mail Australia her friend Leo is “a wonderful person.”
Toni Garrn (May 2013-December 2014)
Another year, another Victoria’s Secret model girlfriend for Leo.
DiCaprio and Garrn “went steady” after they met in Monaco in 2013. They were spotted on multiple getaways in their year-and-a-half-long relationship, including Cannes, Spain, Mexico, Bora Bora and the French Alps.
The pair split following reports that DiCaprio left a Miami nightclub with 20 women. We know Leo likes his ladies, but even that seems a little overzealous from the actor.
Kelly Rohrbach (April 2015 – January 2016)
Before she was an official Baywatch babe, Kelly Rohrbach was already saving lives, one dad bod at a time.
From biking around NYC and partying in the Hamptons and St. Tropez to courtside seats for the US Open, it seemed like this might be the relationship to end Leo’s epic bachelor streak, but alas, even an engagement rumour wasn’t enough to keep these two lovebirds together.
The pair split in early 2016, coincidentally just before awards season, when Leo FINALLY picked up his Oscar for his work in “The Revenant.”
Rihanna (April 2016)
So yes, these two have had a flirty past. The pair sparked rumours in 2015 when they both rang in the new year in St. Barts, reportedly “packed on the PDA” at her February birthday and partied the early part of the year away at various Hollywood events.
But it wasn’t until the Neon Carnival at Coachella in 2016 that people really took notice of how perfect the two might actually be for one another.
Unfortunately for Leo, this was right around the time RiRi and Drake were reportedly heating things up.
Nina Agdal (May 2016 – 2017)
Leo’s latest relationship was with the 25-year-old Sports Illustrated model.
Though their relationship was rumoured to have begun in 2014, it wasn’t confirmed until they were spotted together in May 2016 at New York’s Up & Down.
From there the two enjoyed lots of globetrotting (including a celebratory trip to French Polynesia with Leo’s mom Irmelin), beach PDA, and plenty of partying with his guy gang.
Kate Winslet (THE ONE WE WISH WAS REAL)
Don’t you all just wish these two would forgo the ultimate “support each other through awards season” friendship and just get married already?!
They’ve been friends for over 18 years, absolutely adore one another, and take the best red carpet, BTS after-party shots. Also, Leo’s already walked her down the aisle (during her wedding to rocker Ned Rocknroll), so why not walk her back up it?
Camila Morrone (December 2017 - Present)
After reportedly meeting in Cannes, Leo officially began dating 20-year-old American-Argentinian model Camila Morrone, the stepdaughter of Al Pacino, in December 2017. The actor and model have since been spotted on holiday in Aspen, shopping in Los Angeles, having lunch in New York City and even visiting Ko Phi Phi Le, the island in Thailand where the Oscar winner filmed "The Beach" in 1999.
While many of Leo's past lady loves have stayed silent about their relationships with the star, Camila, now 22, has responded about the couple's age gap, telling commentators on her Instagram to "learn to live with a little less hatred."
And with their relationship appearing to get serious, there are rumours that the famous Hollywood bachelor may finally be ready to settle down.