Leonardo DiCaprio's chaotic dating history – Gisele Bundchen to teen Eden Polan

09 February 2023 , 09:57

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Leonardo DiCaprio has landed in hot water again amid rumours he is dating a young teenage model who "could literally be his daughter".

The Hollywood actor, 48, has never actually publicly dated anyone over the age of 25 and famously split from his long-term ex after her 25th birthday.

Ever since his split from Camila Morrone last summer, Leo has been linked to a string of young models, including his current rumoured flame, 19-year-old Eden Polan.

She is 29 years the Titanic star's junior and the reported romance has come under fire from fans – including popular radio presenter Megyn Kelly.

Megyn sensationally claimed Leo will never find someone "who he can fall in deep love with" - here's a look back at his previous attempts at love in his extensive relationship timeline.

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Leonardo DiCaprio's chaotic dating history – Gisele Bundchen to teen Eden Polan

Leonardo has never publicly dated anyone over 25 (Getty Images for Turner)

Normal 90s

Things looked pretty normal in the 90s for Leo who dated a fair few women, including a rumoured fling with Naomi Campbell in 95, along with a long list of models.

Aged 20 in 1994, he is thought to have had a short fling with US model Bridget Hall, who was 17-years-old at the time – giving them a three-year age gap, one of his smallest.

He dated Kristen Zang on-and-off for four years when they were both in their early 20s between 1995 and 1999, but she now lives in Oregon with her husband.

His history was fairly normal back in the 1990s (CBS via Getty Images)

She previously called him a "very sweet and thoughtful boyfriend".

Between 1997 and 1998, following the success of Titanic, he is thought to have dated Danish model Helena Christensen, model Amber Valletta and actress Bijou Phillips.

The daughter of The Mamas and The Papas singer John Phillips, Bijou, was 18-years-old at the time of their romance, Leo was aged around 24.

Gisele Bundchen

It was his first high-profile romance and Leo met the Brazilian supermodel when she was 20-years-old at the beginning of their relationship, which lasted from 2000 to 2005.

They famously attended the 2005 Oscars together and were always photographed attending sporting games, including basketball.

Leo met the supermodel Gisele when she was 20-years-old (WireImage)

Gisele was 25 when the pair went their separate ways and Leo was 31. "We were just not meant to be boyfriend and girlfriend," she said at the time.

Telling Access Hollywood: "I respect him enormously, and I wish him nothing but the best."

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Bar Refaeli

Following his split from Gisele, Israeli supermodel Bar and Leo's on-off relationship spanned nearly six years, calling things quits in 2011 when she turned 25.

Bar and Leo's relationship spanned nearly six years (Getty Images)

They split in 2011 when she turned 25 (Getty Images)

Leo was 36 when they cut ties – they first met at a party in Las Vegas in November 2005 when Bar was just 20-years-old. They ended over claims neither were "ready to settles down".

It was in-between their relationship that briefly dated Russian American model Anne Vyalitsyna while he was on a six-month break from Bar – Anne was 23-years-old.

Blake Lively

Another brief one... and Gossip Girl Blake met Leo during the 2011 Cannes Film Festival. She was 24-years-old and he was 36 at the time.

Some rumours suggest they began dating after Blake auditioned for the role of Daisy Buchanan in the 2013 film The Great Gatsby.

Blake and Leo ended up dating for five months (Getty Images)

Despite not landing the role – it eventually went to Carey Mulligan – Blake and Leo apparently ended up dating for around five months.

But things have changed and she's now married to Ryan Reynolds, they share three children and a fourth its currently on its way.

Rule of 25

Things continued south from 2011 onwards, with Leo beginning a relationship with US model Erin Heatherton – they lasted around one year, she was 23 and he was 37.

From 2013 he moved to German model and actor Toni Garrn who was 21-years-old at the time, and Leo was 39 – they dated for around 18 months. It's thought they rekindled in 2017, but that seemingly didn't last.

Leo was reportedly linked to singer Rihanna (www.splashnews.com)

They were spotted together a number of times (www.splashnews.com)

In a surprising entry, it was in 2015 that Leo was reportedly linked to singer Rihanna after they were spotted together a number of times – neither of which have ever confirmed a romance.

But if they were together, she would've been the second oldest woman he's dated. She is currently dating A$AP Rocky and they both share a son.

More flings

He dated a 25-year-old Kelly Rohrbach in 2015 for several months, but they reportedly called things off after "intense work schedule" clashes between the US model and actor.

It was in 2016 that he is thought to have briefly dated former Love Island host Laura Whitmore after they were spotted getting close at the Bafta Awards.

Leo and Laura reportedly got close at the Bafta Awards (WENN)

They were reportedly seen whispering at an after-party at the Rosewood Hotel in London, she was 31 at the time – making her the oldest woman Leo had 'romantically pursued'.

Also that year, he began dating Danish beauty Nina Agda – she was 24-years-old and he was about 42. They reportedly called it quits in May 2017.

Camila Morrone

He met a then 20-year-old Camila in December 2017, when he was 43. They were first spotted at Coachella and went on multiple lavish holidays together.

Reports even suggested that Leo was 'ready to ask Morrone to marry him'. They made their red carpet debut at the 2020 Academy Awards.

Leo was 'ready to ask Morrone to marry him' (ABC via Getty Images)

They broke up two years later, when Morrone was 25 years old in 2022.

Camila previously told the Los Angeles Times: "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."

Recent romances

It was last year that Leo was reportedly linked with supermodel Gigi Hadid, she is 27-years-old but sources said it was never "anything serious".

Despite saying the pair "like each other very much", an insider told Page Six: "Gigi doesn’t have the energy to run after DiCaprio. His routine is too much for her."

Leo was reportedly linked with supermodel Gigi (Elder Ordonez / SplashNews.com)

He was also reportedly seeing model Victoria (victoriaalamas/Instagram)

Model Victoria Lamas, aged 23, was also linked to Leo last December after they were spotted leaving a restaurant in Los Angeles – he was still 48.

Her father, actor Lorenzo Lamas, told the New York Post his daughter was "smitten" with Leo, but they were just "friends, they’re not in a serious relationship".

Eden Polan

Leo is now reportedly dating 19-year-old model Eden Polan, who is 29 years his junior. But, a source close to Leonardo claimed there is "absolutely no truth" in the rumours.

The pair had been photographed sitting next to each other at the release party for Ebony Riley's new EP in Los Angles last month.