Leonardo DiCaprio and the Many Ladies in His Life
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Leonardo DiCaprio has been mostly out of the spotlight since his lavish Summer spent traveling around the globe, but now he's back to making headlines for his over-the-top ways. Leo, who may have recently split from his model love Toni Garrn, reportedly left a Miami club with 20 girls while he was partying during the city's annual Art Basel event. He just turned 40 and has a seriously impressive résumé, and it's also obvious that he has had more than his fair share of girlfriends, admirers, and female friends. Take a look back at all of Leo's lovely lady friends — from ex-girlfriends Gisele Bündchen and Blake Lively to best pal Kate Winslet.
Leo rode a bike through Spain with his latest girlfriend, Toni Garnn, in August 2013.
At the March 2005 Academy Awards, Leo walked the red carpet with then-girlfriend Gisele Bündchen on his arm.
Leo and his Victoria's Secret Angel girlfriend Erin Heatherton rode bikes in NYC together in June 2012.
Leo and Blake Lively got cozy on Steven Spielberg's yacht in Cannes in May 2011.
He shared a kiss with a costar while filming a party scene on a boat for The Wolf of Wall Street in LA back in February 2013.
Leo reunited with Kate Winslet in December 2008, stepping out on the red carpet at the LA premiere for their film Revolutionary Road.
Leo chatted with Kate Hudson at a charity dinner in Malibu in June 2011.
Leo and then-girlfriend model Kristen Zang held hands on the red carpet at the Romeo + Juliet premiere in November 1996.
Charlize Theron and Leo linked up to present an award at the GLAAD Media Awards in April 2013.
Cameron Diaz and Leo attended a Tag Heuer event in November 2012.
In November 2011, Leo posed with Naomi Watts at the afterparty for their film J. Edgar.
Leo filmed scenes for The Great Gatsby with Carey Mulligan in December 2011.
In November 2012, Leo locked lips with his Wolf of Wall Street costar Joanna Lumley while filming in NYC.
Leo mingled with friend Courteney Cox at an event in Malibu back in June 2011.
He was the center of a stunning sandwich at the Giorgio Armani Privé runway show in 2007 — front row next to Penélope Cruz and Beyoncé.
Leo and his rumored flame, Romanian-born model Madalina Ghenea, were spotted on a hotel balcony in Australia in October 2011.
At the 2005 premiere of The Aviator in Rome, Leo posed in pinstripes with a gold-clad Cate Blanchett.
Leo and Bar Refaeli hit the beach during a vacation in Mexico in January 2009.
A young Leo and Gwyneth Paltrow posed together at a cinema event in February 1994.
He won the best actor Golden Globe award in 2005 for his role in The Aviator and smiled for photos backstage with best actress winner Hilary Swank.
Leo stood with a gaggle of retro-chic flight attendants at the January 2003 UK premiere of Catch Me If You Can.
He and his Aviator costar Gwen Stefani were all smiles at the movie's premiere in December 2004.
Leo and Claire Danes embraced on the red carpet at the Los Angeles premiere of Romeo + Juliet in October 1996.
After splitting from Bar Refaeli in August 2009, Leo found the company of a gorgeous blonde in Ibiza.
Leo laughed with Michelle Williams at a press conference for Shutter Island in February 2010.
Leo shared a seemingly flirtatious moment with Emmy Rossum at the Vanity Fair Oscars afterparty in 2007.
He walked the red carpet at the December 2004 premiere of The Aviator with his gorgeous costar Kate Beckinsale.
He and his Blood Diamond costar Jennifer Connelly smiled together on the red carpet at the movie's premiere in December 2006.
Leo and costar Vera Farmiga attended the red carpet premiere of The Departed in October 2006.
Leo caught the attention of a lucky lady in a Saint-Tropez nightclub in August 2009.
Leo attended the July 2010 premiere of Inception with costars Ellen Page and Marion Cotillard.
He posed with Meryl Streep at the BAFTA Tea Party in January 2012.