Sienna Miller's Shady Dating History (And Who Is She With Now?)

Sienna Miller's dating history has been shady, to say the least. On several occasions, she was close to making the list of celebrities who had affairs that ruined their careers, and yet, she always bounced back. Part of that may be thanks to the fact that she's been transparent about her often rocky relationships, including opening up about Jude Law's cheating scandal and admitting she doesn't believe in monogamy.

Her ability to be so honest about her personal ups and downs is exactly why she didn't shy away from starring in Netflix's "Anatomy of a Scandal" in 2022. Art imitated life when Miller was cast to play the wife of a British member of parliament whose husband has an affair that lands him in the tabloids. Speaking with The New York Times that April, she admitted that shooting the show was a cathartic experience because she allowed herself to revisit past wounds and draw from them. The actor also spoke about her love life in general and was adamant that she doesn't care much about others' opinions. "You think you know me. Trust me, you don't," she proclaimed. "What do I wish people knew? I don't." Despite said wish, Miller and her beaus can't seem to stay out of the tabloids, which don't always paint her in the most flattering light. Here's everything we know about Sienna Miller's shady dating history, as well as who she's with now.

Sienna Miller and Jude Law first met on the 2003 set of "Alfie" and got engaged the following year, per Elle. However, their relationship was rocked by a tabloid-making cheating scandal in 2005. That year, Miller (and the rest of the world) discovered that Law had been cheating on her with his kids' nanny, per the Daily Beast. "I was in so much shock over it all," she told the mag. She was heartbroken, but Law was persuasive. "He is so sorry for what he did," a source told Sunday Mirror (per Digital Spy). "He is absolutely distraught and is desperate to make amends." In the end, she conceded and gave him another chance –- then did to her beau exactly what he had done to her.

Miller co-starred with one of Law's best friends, Daniel Craig, in 2004's "Layer Cake," and according to Daily Mail, they had a two-week affair. "He cannot believe that she has done this to him," a source told the outlet. "Especially as she always goes on about the importance of monogamy." The insider also alleged that Miller was out to get even with Law. "Since they got back together, she has treated him so badly, going out all the time and not telling him where she's been going," they claimed. The pair eventually split for good, but Miller maintained her time with Craig was misreported. "It was not a relationship; it was a very brief encounter," she said, per Telegraph.

The year before Gisele Bundchen agreed to a fateful blind date with Tom Brady, she was dating another A-lister, Leonardo DiCaprio. The pair got together in 1999 but called it quits in 2005, sparking major speculation about the real reason they broke up. Years later, the supermodel addressed the relationship in her 2018 book, "Lessons: My Path to a Meaningful Life," per USA Today. In it, she recalled her decision to overhaul her bad habits and focus on her mental health and mused, "Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes." Meanwhile, her father, Valdir Bundchen, told Daily Mail that hectic work schedules were to blame for the young couple drifting apart. "For people in the movies and in the fashion world, their downtime is very short," he reasoned. "Sometimes relationships pay the price."

Well, there may also have been another reason for their split: Sienna Miller. One source told Fox News, "Gisele was tired of Leo and all his screwing around," and she apparently called it quits after DiCaprio got a little too close to Miller. Indeed, they were spotted partying together on two occasions at the end of 2005. "There was a lot of flirting going on," a source told London Mirror, per Today. However, Digital Spy reported that while they did meet in 2005, they didn't start dating until 2006. "As they spent more time together, their feelings for one another blossomed," the source claimed.

When Sienna Miller and Keira Knightley met on the 2008 set of "The Edge of Love," they became fast friends. As Knightley told Vogue, per British Vogue, it all started with some after-work drinks. "I'd just broken up with a boyfriend, and she decided getting drunk and making total fools out of ourselves was the only way through," Knightley recalled, quipping, "She was totally right." The admiration was mutual. "Keira is the most beautiful woman in the world," Miller told Telegraph. "We totally bonded on the movie, and it was so amazing to find a girlfriend in the business!" Said bond proved to be long-lasting, and Miller was still gushing about her bestie in 2015, telling Jolie magazine, per British Vogue, that she's "the most beautiful woman I've ever seen."

However, their relationship hit a temporary snag when Knightley and Jamie Dornan broke up in 2005 after two years together, per People. As Dornan told Belfast Telegraph, he couldn't handle Knightley's fame. "You can feel a bit second-rate, and that's what started to happen," he admitted. Well, that didn't bother Miller, who reportedly went on some dates with Dornan in 2006. Her BFF didn't exactly approve. "She was horrified when she heard Sienna has enjoyed a series of dates with Jamie," a source told Daily Star (via The Sun). "She likes Sienna and doesn't want to see her make the same mistakes." According to the source, Miller clapped back, "I'm a big girl, and I'll make my own mistakes."

Sienna Miller's shady dating behavior continued in 2007 as she was accused of getting in between Sean "Diddy" Combs and his longtime girlfriend, Kim Porter. In December 2006, Diddy and Porter, who already had an 8-year-old son named Christian, welcomed twin daughters, per The Hollywood Reporter. The rapper was reportedly overjoyed as his rep proclaimed, "Diddy received an early Christmas gift." Well, that didn't stop him from partying the night away with Sienna Miller the following month during the Sundance Film Festival. On January 23, Digital Spy reported the pair got cozy in Utah, and just days later, on January 29, TMZ caught them partying in New York. What's more, Diddy was spotted dropping her off at her hotel afterward.

Rumors that Miller and Diddy were dating began to swirl and weren't helped when, in July 2007, Miller arrived in New York to promote a film at the same exact time that Diddy confirmed his split from Porter, per Evening Standard. What's more, just five days earlier, they were allegedly spotted kissing at a London club, per Daily Mail, as well as having a romantic dinner. Despite all the salacious rumors, Miller dismissed them as just that: rumors. "I am in love with someone but not Puff Daddy," she said, per Irish Examiner. "He's just a good friend; anyway, he has a beautiful girlfriend." Despite her denials, outlets like Daily Mail couldn't help wondering if Miller was the real reason behind Diddy's split, given the timing of their encounters.

In 2008, Sienna Miller began dating fellow actor Rhys Ifans, per Daily Mail, and she appeared to be completely smitten. "When his name is mentioned, it makes me smile like a fool because I instantly think of him, and it makes me happy," she told Elle UK (via People) in May 2008. "I totally love Rhys." Well, that sentiment seemed to have completely disappeared by the following month. Jump to June 2008, and Miller not only broke up with Rhys but reportedly did so by phone, per The Sun (via Marie Claire UK). An insider told the outlet Miller caught her beau reading her texts for clues of infidelity, and eventually, she drew a line. "She couldn't cope with his suspicious and jealous behavior," the source claimed. However, Ifans may not have been totally off the mark in his suspicions. Turns out, Miller simply didn't want commitment. "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," she confessed, per Daily Mail.

Being selfish meant leaving Ifans heartbroken and reportedly homeless because, according to MailOnline, he had sold his place to move in with Miller. Ifans' high-profile friends, including Kate Moss, were reportedly unimpressed with Miller's inconsiderate actions. "Although she comes across as all sweetness and light, they think her actions show what a horrible person she is underneath," a source slammed, per Evening Standard.

Sienna Miller experienced the pain of being cheated on first-hand with Jude Law, and yet, she's since had more than one affair of her own. Just a few weeks after she broke up with Rhys Ifans, it was revealed that she had simultaneously been seeing fellow actor Balthazar Getty, per People. As if that wasn't enough, he was actually married at the time and had welcomed his fourth child with wife Rosetta just 10 months earlier. 

The couple's questionable behavior was exposed in July 2008 when Miller was spotted vacationing in Italy with Balthazar and the infidelity was proven by photos of a topless Miller kissing him on the Amalfi Coast. The Gettys separated soon after, per Us Weekly, but when Balthazar and Miller broke up in May 2009, he and Rosetta reconciled. Speaking with Harper's Bazaar, per People, in 2010, Rosetta explained why she decided to forgive her husband. "I chose not to act from ego because I just felt like it would be too crushing for my children," she shared.

As for Miller, she eventually appeared to regret the affair, at least sort of. "I do think sometimes people get morally superior without understanding situations," she told British GQ, per Us Weekly, in August 2009. "And the situation I got into was not ideal, but it happened, and if I could go back and be more responsible, I would." So what would she have done differently? "Well, I probably would be less naive about ignoring the fact that people care," she mused.

Sienna Miller simply can't seem to stop making headlines with her love life. Back in 2015, Miller filmed "The Lost City of Z," which was produced by Brad Pitt's production company, Plan B. Despite Pitt being married to Angelina Jolie at the time, there were rumors that the pair had been flirting on-set, per Page Six. Miller, who split from fiance Tom Sturridge in July 2015 (the pair welcomed daughter Marlowe in 2012), was adamant that there was nothing going on. Saying that Pitt didn't attend the shoot, she assured, per Us Weekly, "He's the producer of the film, and I've met him twice."

However, that wouldn't be the last time the couple was linked. In April 2017, while promoting the film, Miller and Pitt were reportedly spotted flirting at a Los Angeles restaurant, per Page Six. Miller quickly brushed off the gossip. "I'm not going to even dignify it with a response," she told Page Six. "It's predictable and silly." Even so, news of a possible romance between the two heated up when they were reportedly seen holding hands at the Glastonbury music festival in June 2017, per The Sun. "Brad and Sienna couldn't keep their hands off each other, touching and stroking each other at every opportunity," a source claimed. "They seemed really intimate." At the same time, another insider told Us Weekly, "There's nothing going on there."

Sienna Miller had already called off engagements with Jude Law and Tom Sturridge when, in 2020, she stopped another wedding-to-be in its tracks. Following her split from Sturridge in 2015, Miller told Elle UK she had been single for nine months and that it was a new experience for her. "It was about the first time in my life I'd ever been single," she admitted. "It was fine." She eventually started dating again and says she didn't click with anyone until she met Lucas Zwirner, the son of gallery owner David Zwirner. "He's not an actor! He's not famous!" she gushed. After a year together, Miller and Zwirner got engaged in February 2020, per Us Weekly. According to one insider, Zwirner had a great relationship with Miller's daughter, Marlowe, and the couple was absolutely in love. However, that August, Miller suddenly called it quits, per Page Six.

In 2022, the actor addressed her string of failed engagements with DuJour magazine, admitting, per Daily Mail, "I was never somebody who dreamt of getting married." She then made a surprising joke at her own expense. "I've been engaged a few times, but I've never been married," she said, quipping, "It's better than three divorces, I think."

On January 30, 2022, Sienna Miller was spotted kissing Cara Delevingne at a New York City bar. However, according to a source who spoke with Page Six, it wasn't just the two BFFs who shared a smooch that night. "It was like fluid friends," the insider claimed. "Sienna made out with this tall guy, and then she made out with Cara." Turns out that guy may have been actor Oli Green with whom Miller appeared to share a date just days later on February 3, 2022, per Page Six. Indeed, they've since made their relationship official and have repeatedly been spotted having a great time together, being cute at NBA games, and enjoying Paris Fashion Week. Many folks have honed in on the fact that Green is 15 years younger than his new girlfriend, but as Miller told Vogue UK, that's a good thing. "There's a misogyny that is ingrained in men of my age and older that I don't see in [the] generation below," she mused.

We may not know if Miller's union with Green will end in marriage but what we can be certain of is that, whatever the outcome, she won't ever be apologetic. When The Sunday Times Style asked about her dating history, Miller slammed, "What is the point of listing someone's sexual history? It is totally gendered," she proclaimed, demanding they "apply the same rules interviewing actresses as they do to actors."