Sienna Miller Celebrates Age Gap, Welcomes Second Child

Sienna and Orlando were first linked in 2001, but were later pictured cosying up at a polo match in the summer of 2005.

'They spent ages cuddling, kissing and gazing at each other. There was real chemistry,' a witness said at the time.

Jude Law - 2004 and 2009

Having dated one another for a while, Sienna and fellow actor Jude became engaged in 2004.

But a year later they split up, when it came out that Jude had had an affair with his children's nanny.

Jude - now a father-of-five - famously issued a public apology after the scandal emerged, and Sienna has said recently: 'We don't see each other that much. I care about him enormously.'

They attempted a reconciliation in 2009, but this didn't last. The news came that they had split for good in 2011.

Daniel Craig - 2005

Sienna admitted in 2014 that she and James Bond star Daniel enjoyed a 'brief affair' in 2005 having met during the filming of 2004's Layer Cake.

It's assumed this took place after the revelations that Jude had cheated on her in 2004.

Leonardo DiCaprio - 2005

Sienna was said to be the reason Gisele Bundchen dumped Leo.

It's said he was seen looking very close with Sienna in a club in LA one night, leading to the split.

Jamie Dornan - 2006

Sienna reportedly enjoyed several dates with the would-be Fifty Shades Of Grey hunk, much to the chagrin of her friend, and his ex, Keira Knightley.

A source at the time said: 'Keira went through hell with Jamie, because he couldn't deal with her fame. She was horrified when she heard Sienna has enjoyed a series of dates with Jamie. She likes Sienna and doesn't want to see her make the same mistakes.'

Sienna's response was apparently: 'I'm a big girl and I'll make my own mistakes.'

Josh Hartnett - 2007 and 2009

Josh and Sienna were allegedly caught flirting at Hollywood hang out Chateau Marmont in January 2007.

It was denied - but onlookers claimed the hunky actor had his hand on her thigh at one point. 

They were also seen together in 2009 various times, it has been reported.

P Diddy - 2007

The rapper was pictured entering Sienna's New York hotel at 9AM with her after a night of partying in 2007.

They were then seen together frequently, at clubs and on yachts.

The American musician split from the mother of three of his children shortly after the birth of their twins - and Sienna has often been blamed for this.

Jamie Burke - 2007

2007 proved a busy year for Sienna who was apparently so serious about musician Jamie that she introduced him to her parents in New York that year.

He counted the likes of Kate Moss, Lindsay Lohan and Courtney Love as his past conquests - but the dalliance with Sienna was over fairly swiftly. 

Matthew Rhys - 2007

Welsh actor Matthew fell for Sienna while filming Dylan Thomas biopic The Edge Of Love. But this did not last.

'Sienna is so fun loving, a real free spirit, which comes from not really caring what other people think,' he told the Daily Mail afterwards. 'Unfortunately, classic things came between us, like distance. We spent so much time apart.'

Matthew then went on to star in TV's Brothers & Sisters, as the brother of Sienna's next lover.

Balthazar Getty - 2008

American actor Balthazar - son of John Paul Getty III who was famously kidnapped and held at ransom as the grandson of the once-richest man in the world - famously left his wife and their four children for Sienna after having an affair with her. 

Despite the high-profile scandal, Sienna flaunted the affair, famously pictured topless on a boat with Balthazar while his devastated wife went into hiding.

Sienna admitted later than she 'looked like not a nice person' and blamed it on being in her 20s.

Balthazar's public drama affected his job on TV show Brothers & Sisters at the time, and he had to reduce is time on the show. He eventually went back to his wife.

Rhys Ifans - 2008 

Thought to have been introduced via her Primrose Hill gal pals Kate Moss and [Jude's ex-wife] Sadie Frost, Sienna started dating Notting Hill actor Rhys who were reportedly first spotted together getting amorous on a plane.

She was 26 at the time and when she split from Rhys - claiming she 'wanted to be selfish for just a little bit longer' - it reportedly devastated him. He was said to be left homeless after they set up house together.

Tom Sturridge - 2011 - 2015

Sienna had a daughter, Marlowe, with actor Tom a year after they got together.

Despite their eventual split, she told Harper's Bazaar in 2017: 'He is my best friend in the entire world. 'I think in a break-up somebody has to be a little bit cruel in order for it to be traditional, but it’s not been acrimonious in a way where you would choose to not be around that person.

'We don’t live together, as has been reported recently, but we do half the time. Everybody will stay over or we’ll all go on holiday and that’s because we genuinely want to be around each other.

'It’s great for our daughter that she has two parents who love each other and are friends. He’s definitely my best friend in the entire world.'

The pair were engaged in 2012. Their eventual split have never been truly known.

Brad Pitt - 2017

Having split from his wife Angelia Jolie, rumours began circling Brad and Sienna in 2017 when they were snapped in April 2017 at an LA restaurant together, after the premiere of their project The Lost City Of Z.

She slammed rumours that they were romantically linked, branding it 'predictable and silly'.

That summer, however, they enjoyed a 3AM rendezvous during the Saturday morning of Glastonbury 2017.

It's said they spent time together at the festival’s exclusive Rabbit Hole area before disappearing to a VIP Winnebago. Onlookers claimed they 'couldn't keep their hands of each other'.

Lucas Zwirner - 2019 

The actress went public with her relationship with art gallery owner Lucas in Janaury 2019, after being introduced through mutual friends.

In January 2020, she was spotted with what looked like an engagement ring, while out and about in New York.

There is a 10-year age gap between the pair.