Sienna Miller's Relationships Through The Years

In August 2023, Sienna Miller let the world know she is expecting her second child at the age of 41. The announcement arrived in a People exclusive, which featured photos of the stunning actor hanging out on a beach and wearing a bikini that highlighted her baby bump. This will be her second child. Though she has not confirmed the father's identity, it's believed that Oli Green, a model who Miller has reportedly been seeing since August of 2022, is the baby daddy. Green, who bears more than a passing resemblance to Miller's former flame Jude Law, is the latest in a string of headline-making relationships that read like a who's who of Hollywood. 

Miller has given the tabloids plenty of fodder over the years with the famous men she's left in her wake. In fact, there was a time when the former model was known more for her romances than her roles. And while she admitted to Vogue in 2009 (via Us Weekly) that she does fall in love easily, she doesn't see herself as a serial dater. "I'm a real relationship person, contrary to public perception," she said. Still, with a couple of scandals, three failed engagements, and a famous betrayal in her background, Miller's love life has been the subject of much scrutiny. Let's take a look at the ups and downs and unconfirmed rumors that make up the talented actor's relationship history.

In 2022, Siena Miller starred in the Netflix series "Anatomy of A Scandal," the story of a politician's wife whose husband's affair became a public circus. Miller didn't have to dig too deep for inspiration. In a case of art imitating life, Miller's fiancé Jude Law was caught cheating on her in 2005 with the nanny of the three children he shares with ex-wife Sadie Frost. Up until that revelation, the golden duo who met on the set of "Alfie" in 2003 seemed to have it all, which made the scandal all the more headline-worthy. Although the actor issued a public apology for his actions, apparently, it was not enough, and Hollywood's latest "it" couple called it quits.

Miller, who was just 23 at the time, has since reflected on the impact of that very public humiliation. "There's a whole six weeks of that experience that I don't remember," she told the Daily Beast in a 2020. "I have no recollection of it." They split up in the wake of the scandal, and a few years later they tried again. The second act ended in 2011, but there was less drama that time around — and it gave Miller a sense of closure. She told news.com Australia, "When something ends in a way like that, it's important if you can, in a way, go back and revisit it and either shut that door or create a new room. So it was a very healthy, cathartic experience."

While Sienna Miller came off as the heartbroken victim in the Jude Law scandal, details emerged during a 2014 British phone hacking trial that suggested that the beautiful bad girl might not have been as innocent as she seemed. According to CNN, tabloid journalist Dan Evans hacked the voicemail of Daniel Craig in 2005 and discovered a message from Miller to her "Layer Cake" costar. In the message, Miller (who never states her name) says she is out with Law and can't speak, but declares "I love you" before hanging up. The tabloid spying led to rumors of an affair between Miller and the sixth James Bond, which Miller didn't exactly deny. 

During her testimony regarding the case, CNN reported that Miller admitted that she probably did utter those three little words, but not in the way that the tabloid led people to believe. "For a long period of time, he was one of my closest friends," she said of Craig. "That's how I ended all my calls to my friends." However, later in the testimony, she ambiguously said that while she did not have a "relationship" with Craig, she did have a "brief encounter" with him. We may never know the full story, but it is clear is that there was, at the very least, friendly communication between Miller and Craig while she was reportedly dating Law. Just how friendly appears to be top secret. 

What happens when two serial daters hook up? Sparks fly and then fizzle. That was the case with Sienna Miller and former Calvin Klein model and musician Jamie Burke, who dated for just eight short months in 2007. Burke, who once fronted the band Bloody Social, has a celebrity relationship resume that almost makes Miller look like an amateur. Before meeting the blonde bombshell at an event for the 2006 flick "Factory Girl," Burke had been linked to the likes of Kate Moss and Lindsay Lohan, to name a few. The pair with the enviable hair seemed to hit it off quickly, with Miller often seen visiting her new beau in New York. Things appeared to be getting serious when they were spied sharing a Mexican getaway, complete with topless beach strolls and oceanside serenades. As the Daily Mail reported at the time, after the trip, Miller went to dinner with Burke and her parents.

Despite the family meet and greet, the couple didn't last much longer. According to team Miller, the split was her idea and due primarily to the fact that they were separated by an ocean. She told the Evening Standard, "I am at the point of my life where if I am going to be in a relationship, I don't want to be on the phone for an hour a night." Some people in the Burke camp had other speculations as to why the pair split — namely, that he was unhappy with rumors about Miller possibly connecting with Diddy.

Sienna Miller was a very busy girl in 2007. After calling things off with Jamie Burke, she wasted no time in moving on to her "The Edge of Love" costar, Matthew Rhys, whom she met through mutual friend and costar Keira Knightley. Although "The Americans" star described Miller in the Daily Mail as "fun loving" and a "free spirit," the pair didn't last long. "But, unfortunately, classic things came between us, like distance," he told the outlet. "We spent so much time apart." 

Now, here's where things get interesting... and confusing. Miller moved on from Matthew Rhys to "Notting Hill" star Rhys Ifans in August of 2007, less than a month later. The unlikely pair dated until May 2008 — right around when Miller was promoting "The Edge of Love" with the other Rhys. Per Marie Claire, sources claimed to The Sun that Rhys Ifans was apparently jealous of Miller and Matthew Rhys, and his behavior finally drove Miller to end things via a phone call. (Guess that's better than getting a Post-it note — just ask Carrie Bradshaw). On top of getting dumped, Rhys Ifans also had to figure out his housing situation, as he'd sold his place to move in with Miller.

Though the split was a bit messy, Miller seemed to have no regrets. Per the Daily Mail, she told a reporter, "I really thought I was very ready to settle down, but then I realized I wanted to be selfish for just a little bit longer."

The Rhys saga took another weird turn when Matthew Rhys discovered that the small screen wasn't the only thing he shared with his "Brothers and Sisters" costar Balthazar Getty. After meeting the very married Getty through Rhys, Getty and Miller began an illicit affair that nearly broke up his marriage in 2008. As People reported at the time, the two were photographed canoodling on a hotel balcony and on a yacht — and she wasn't always totally clothed in said images. The photos caused some pretty big waves in the lives of both the actor and the oil industry heir. The latter separated from his wife, Rosetta Millington.

Branded a "homewrecker," Miller reportedly ended the affair rather swiftly. As she said in a 2009 interview with Vogue (via Marie Claire), "I got to the point where I was doing things that I didn't necessarily think I was capable of as a person." As for Getty, he returned to his wife and kids. In a 2010 interview with Harper's Bazaar, he called the affair "a challenging time" and praised his wife for her willingness to give him another shot. "Rosetta is understanding enough and spiritual enough to let us try," he said. "In a way it — I don't know ... I feel like we're better than we've ever been."

As previously noted, Sienna Miller briefly returned to former flame Jude Law following the Balthazar Getty scandal, but it wasn't long before she moved on with actor Tom Sturridge. The couple began seeing each other in 2011, became engaged and welcomed daughter Marlowe in 2012, and shot a smoking hot ad campaign for Burberry's 2013/2014 collection. Sexy, stylish, and seemingly madly in love, they really appeared to have it all. That is, until they didn't. The pair called time of death on the romance in 2015, but not the friendship, which is still going strong all these years later. 

In one of the most be one of the most amicable celebrity splits to make headlines, Miller and Sturridge are often spotted hanging out together with, and sometimes without, the significant others in their lives. Miller and current beau Oli Green were recently seen being friendly with Sturridge and his girlfriend Alexa Chung at Wimbledon 2023. In a 2017 Harper's Bazaar interview, the "American Woman" star admitted that she and Sturridge "still love each other," noting that they are happy to travel together. When it comes to their daughter, the exes have co-parenting down to an unconventional science, with the three of them often spending the night together at Miller's New York apartment. "It's great for our daughter that she has two parents who love each other and are friends," she said. "He's definitely my best friend in the entire world.'

Sienna Miller and her two-time costar Bradley Cooper struck up a real-life friendship — and as far as we can tell, their relationship has remained platonic over the years. However, rumors have swirled about Miller and someone named Brad — but it wasn't Cooper. It was Cooper's buddy Brad Pitt. Miller played Nina, the wife of Jack Fawcett in 2017's "The Lost City of Z," a movie produced by Pitt's company, Plan B Entertainment. Pitt was originally slated to play Fawcett but had to withdraw due to a scheduling conflict. So while the genetically blessed blonds didn't play husband and wife on the big screen, rumor has it they connected behind the scenes. Tabloids claimed that some serious flirting was going on at a 2017 post-premiere private dinner, but Miller denied that she and Pitt were involved, telling a reporter from Page Six, "I'm not going to even dignify it with a response. It's predictable and silly,"

Silly or not, the rumor didn't entirely die. Later that same year, The Sun reported that they were spotted getting cozy while at the Glastonbury Festival with friends, including Cooper. Apparently, the pair was very touchy-feely and reportedly went back to a private trailer together in the wee hours of the morning. Despite the reported canoodling, the two were never officially linked as an item, and Miller began a relationship with fiancé number three, Lucas Zwirner, shortly thereafter; Pitt continues to keep his private life, well, private. 

Deemed the "Ultimate Manhattan Couple" by Vogue in 2020 for their understated city style, Sienna Miller and former fiancé Lucas Zwirner looked like a match made in heaven. The two met in 2018 and dated for close to a year before he supposedly put a ring on it in January 2020. Like her other two ill-fated engagements, this one did not end in a walk down the aisle for Miller. Instead, it ended in a breakup just nine months after the reported engagement. Although the details of what drove them apart were not revealed, Miller told DuJour, "I was never somebody who dreamt of getting married." And those three broken engagements? "It's better than three divorces, I think."

True to Miller's style, the plot thickens. Not long after the breakup, Zwirner was spotted out and about with Maya Hawke. What does that have to do with Miller? Maya, the daughter of Ethan Hawke and Uma Thurman, was previously linked to Tom Sturridge, Miller's former fiancé and father of her daughter. To add to the tangled nature of the tale, Miller and Zwirner made one of their first public appearances in 2018 at Sturridge's birthday party.  We know, we know, it's hard to keep up. Although sources in both the Zwirner and Hawke camps denied anything other than friendship between the two, it does seem that Miller's dating world is a small one.

Model/actor Oli Green may be 15 years her junior, but that doesn't seem to be keeping Sienna Miller's new man from stepping into the role of dad. Miller, who told Elle that she had some of her eggs frozen when she turned the big 4-0, announced in August 2023 that she is pregnant. She did not say whether or not she used one of those eggs, nor did she specifically name Green as the father. However, Miller has been seeing the actor/model since 2022, so we think it's safe to say he is part of the equation in some way. And, as mentioned before, the pair were hanging with Miller's ex Tom Sturridge at Wimbledon in 2023, so it seems as though they are all one big, happy family. 

Green comes into the relationship without any children of his own, but Miller, who has a child from a previous relationship, should be able to give him plenty of pointers. Of all the roles she has played in her career, it is the role of mom that she cherishes most. She told People in 2019, "When you are raising a child you see aspects of your character in that person, reflected back, and it's the most loving, intense relationship that I have."

Miller hasn't said a ton about Green, but she has offered hints about their connection. She told British Vogue in 2022, "there's a misogyny that is ingrained in men of my age and older that I don't see in [the] generation below."