Red Flags In Shailene Woodley's Dating History

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Actress Shailene Woodley has fronted the young adult franchise "Divergent," picked up a Golden Globe nod for her performance in comedy drama "The Descendants," where she established a strong bond with George Clooney, and held her own with Nicole Kidman, Laura Dern, and Reese Witherspoon in watercooler mystery "Big Little Lies." And let's not forget her work on Broadway, as an environmental activist, and co-founder of the youth development program All it Takes. But lately, the actor has become more renowned for her love life than her considerable career achievements.

Interestingly, Woodley didn't give the tabloids much ammunition for the first decade of her career, even once taking a long break from acting. But she's made up for that in recent years thanks to a string of high-profile relationships with everyone from vaccine-denying NFL quarterbacks to heartthrobs from Netflix's fluffiest rom-com. Of course, anyone who's kept up with the trials and tribulations of the star's love life is unlikely to be surprised that they all ended. Here's a look at the red flags that suggested each and every new romance was ultimately doomed.

Shailene Woodley has played numerous characters in unorthodox relationships on screen. Take "Endings, Beginnings," for example, where she portrayed a 30-something who starts seriously dating two men at the same time. And in "Robots," she pulled double duty as a rich suburbanite and an android programmed to date multiple humans for money. As it turns out, the actor has plenty of experience off-screen, too.

In a candid chat with The New York Times, Woodley revealed she's been in both monogamous and open relationships, and that she doesn't believe that traditional rules apply in the 21st century. "I think we're in a day and age where there should be no rules except for the ones designed by two people in a partnership — or three people, whatever floats your boat! But there has to be a level of responsibility in any relationship dynamic, and that responsibility is simply honesty and communication and trust."

Woodley, whose past lovers included rugby union star Ben Volavola and rock star Nahko, also discussed being in an open relationship during a similarly revealing interview with Bustle: "I had a lover that taught me a lot about my own body and my own emotional connection to sex. That's when I feel like I healed my relationship with sexuality — when this beautiful man came into my life and helped me walk through that journey." Could this liberal attitude have played a part in any of her high-profile break-ups?

The sometimes-shady Shailene Woodley looked to have found 'the one' when she started dating Ben Volavola, a rugby union star who plays for the Fiji national side. The pair first got together in 2017 while the former was shooting the disaster movie "Adrift" and the latter was competing in the Pacific Nations Cup. And three years on, the sound of wedding bells appeared to be on the horizon.

But in 2020, the couple decided to call it quits. Well, at least one party did anyway. In a revealing chat with Bustle, Woodley revealed that even though she'd still regularly lie on the ground and unleash the waterworks, it was she who instigated the break-up. So what happened?

"I was in a relationship with someone and we were very much on the road to marriage and children," Woodley said. However, after experiencing an epiphany on the set of the love triangle drama "Endings, Beginnings," the actor acknowledged that she wasn't quite ready for domestic bliss. "I realized I was still at an age where I wasn't able to fully commit. I couldn't be available to him in the way that I wanted to be. I didn't fully love myself."

In 2017, Shailene Woodley was cast in the award-winning drama "Big Little Lies" as Jane Chapman, a single mom whose young son had been fathered by a domestic abuser. Sadly, as she told The New York Times three years later, the star, was able to draw from a similar experience herself.

Woodley explained that the strong sense of identity she had in her late teenage years took a major hit when she began seeing an unnamed individual who displayed abusive behavior. "That combined with, honestly, the commercial success I had in this industry began to wear on my strength. My 20s felt a little bit like being in a washing machine, where you're being thrown all over the place." Could this traumatic experience have impacted on her future relationships, too?

While discussing her role in the award-winning drama with IndieWire, Woodley argued that societal expectations are to blame for such abuse. "There's not a lot of empathy for what it must be like to be young boy in a world that [either] demands violence because that's what makes you strong and brave, or, if you are not operating from that place, you're weak. You're given a certain label [no matter what], and I think that's where a lot of violence stems from."

Shailene Woodley's attitude to singledom appears to constantly shapeshift. In 2014, the year she landed her most high-profile role in the "Divergent" series, the actor told Marie Claire that she was more than happy flying solo. "I just haven't met anyone where I was like, 'Wow, I could definitely see myself spending a season of my life with you.'"

However, Woodley later entered into several long-term romances, firstly dating Medicine for the People frontman Nahko Bear and then Fijian Australian rugby star Ben Volavola before claiming that she now wanted to spend some quality time alone. "I was trying to use relationships to distract me from getting to know myself," she told Bustle shortly after splitting with the latter. "I can't run from myself. I can try, but my house is not that big."

But was this a case of doth protest too much? Later that very same year, Woodley began stepping out with another sportsman, a relationship that would propel her onto the front pages of gossip magazines more frequently than ever before!

"We're societally conditioned to assume that one person can be our end-all, be-all," Shailene Woodley told The New York Times while promoting "Endings, Beginnings" in 2020. "This is a concept I've been thinking about often right now, because I'm very much single, and I've chosen to be single for a while."

Of course, as we all now know, before the end of that same year, Woodley was very much not a proud single woman. In fact, she'd started dating the man she very nearly walked down the aisle with, NFL quarterback Aaron Rodgers. And she was also keen to let everyone know about it, too.

Woodley described him as "super sexy, super attractive" in an Instagram story promoting his hosting stint on "Jeopardy!" During a chat with The Hollywood Reporter, she hailed him as a "wonderful, incredible human being." And while being interviewed on vacation in Disney World, she told her new beau (via the Daily Mail), "Oh! You're so cute, baby!" Playing it cool obviously isn't the "Ferrari" star's style.

Of course, the rumor mill surrounding Shailene Woodley and Aaron Rodgers' relationship went into overdrive when the unlikely couple confirmed they were an item in early 2021. How on earth did they meet? What could they possibly have in common? And perhaps most pressing of all, did they do the dirty on the quarterback's ex-girlfriend?

Both the online world and those who knew the couple were left wondering when exactly the couple got together. In April 2020, Woodley had insisted to The New York Times that she was young, free, and single. Three months later, Rodgers announced his split from one-time professional racing driver Danica Patrick. And at some point, during the pandemic, soon after, the unlikely pairing decided to move in together.

Patrick herself never commented on the allegations, but that didn't stop tongues from wagging. And she put the cat among the pigeons with a cryptic Instagram post she uploaded when Woodley and Rodgers eventually split, captioning an oceanside photo (via Showbiz Cheat Sheet), "The funny thing is ... we know. We always know deep down what's good for us and what's bad. If you wonder, just ask. The answers are usually short and sweet. They may not always be what you want, but they're what you need."

Sure, we know that Hollywood stars move a lot faster than us mere civilians. Even so, Shailene Woodley and Aaron Rodgers still surprised everyone when they revealed they'd moved in together just months after they first became an item.

"I was by myself with my dog and didn't see anyone for three months," Woodley told Shape magazine about her home situation during the pandemic, perhaps explaining why the "Dumb Money" actor was so quick to start sharing wardrobe space with the Green Bay Packers icon. "It forced me to be still and quiet," she added.

It was unlikely to be still and quiet much when Woodley started shacking up with Rodgers, a footballer renowned for speaking his mind. But the Golden Globe nominee told the same magazine that their unlikely union was always written in the stars. "I have the perspective that I would have met Aaron in any context, any space in time, because I feel we were meant to be together."

Having moved in together shortly after they started dating, it was perhaps little surprise when Aaron Rodgers revealed the news that he and Shailene Woodley were engaged just months later. Well, semi-revealed. Although the footballer gave a shout-out to his new fiancée while accepting an award at the NFL Honors staged virtually in 2021, he didn't disclose exactly who this fiancée was.

However, considering Rodgers and Woodley had been the talk of Tinseltown throughout the pandemic, it didn't take a genius to work out their identity. And the latter confirmed once and for all (via People) when she appeared on "The Tonight Show Starring Jimmy Fallon": "Yes, we are engaged. But for us, it's not new news, you know, so it's kind of funny. Everyone right now is freaking out over it and we're like, 'Yeah, we've been engaged for a while.'"

"He's first off just a wonderful incredible human being," Woodley, who had a strange living situation when she was a teenager, continued before admitting that she never once saw herself shacking up with a professional sportsman. "Like I never thought as a little girl, I was like, 'Yeah when I grow up I'm gonna marry someone who throws balls!' But he's really just so good at it. And I'm impressed."

The general public wasn't alone in believing that Shailene Woodley and Aaron Rodgers may be putting their feet on the gas pedal a little too quickly. Apparently, those within their inner circle also expressed concerns about the unlikely couple's rapid sense of commitment.

"It was a surprise that they got so close so quickly," an anonymous insider told People about the pair who moved in together just months after dating and got engaged following a similar amount of time. "I mean, it really felt like one day he was with Danica Patrick, and then suddenly he was with Shailene. It happened super fast." The source also revealed that friends believed their relationship was a simple rebound case until Rodgers got down on one knee.

"Everyone thought it was a casual thing because that's what he was telling everyone, even when it was clearly not a casual thing," the same individual remarked, suggesting that Rodgers was initially keeping his cards close to his chest. "Now we realize that it was clearly a lot more serious than they told anyone. All this goes to show that this must be a very special relationship for him and for her. So everyone wishes them happiness."

Shailene Woodley initially took to Instagram like a duck to water, posting regularly on the photo-sharing platform in a bid to engage her American followers to vote in the Donald Trump versus Hillary Clinton presidential election of 2016, as well as raising awareness of the Standing Rock protests against the Dakota Access Pipeline. But regular users may have noticed that while dating Aaron Rodgers, she went suspiciously quiet.

"It honestly never really hit me that millions of people around the world were actually watching these things and paid attention to them," Woodley told Net-A-Porter about her sudden withdrawal from social media. "It was the first time that I'd had a quote-unquote 'famous' relationship, and I watched [the] scrutiny, opinions, the desire for people to know my life and his life and our life — it just felt violating in a way that, before, it was fun."

Woodley, who subsequently deleted Instagram from her phone, went on to add, "I'm a very private person, and so I found that any time I posted anything, I instantly felt like I was sharing too much of who I am with people I didn't necessarily trust."

One of the reasons many people raised their eyebrows at the news that Shailene Woodley and Aaron Rodgers had become romantically involved was their differing political perspectives. The former had previously pledged her support for Bernie Sanders in two consecutive presidential elections, strongly advocated for various environmental issues, and in 2016 was arrested for protesting against the controversial underground Dakota Access Pipeline. The latter, on the other hand, was very much on the other side of the spectrum, as evident by his more recent championing of Robert F. Kennedy Jr., promotion of anti-vaccine rhetoric, and echoing of numerous conspiracy theories.

So how did the couple avoid constant fights at the dinner table? Well, according to an anonymous People insider, they simply avoided the subject altogether. "They are not talking about their politics, and they never really have. They disagreed on a lot of things. Early on, they decided to agree to disagree about things and not debate them."

"She is not someone whose mind you can change, so Aaron hasn't even tried," the insider claimed about Woodley's beliefs. However, some might now say that's not true. Indeed, the "Killer Heat" star came under fire in 2024 for describing Melania Trump's response to her husband's assassination attempt as "This is so beautiful." An unrepentant Woodley later told Bustle, "Hundreds of articles because I posted about a woman saying she's grateful her husband is alive? Really?"

After splitting from Aaron Rodgers in 2022 and appearing to blame him in the process, things on the relationship front appeared to go quiet for Shailene Woodley. But three years later, "The Last Letter from Your Lover" star became a tabloid fixture again when she started dating "Emily in Paris" hunk Lucas Bravo.

"Yeah, I'm really happy," Bravo told People when asked about his new relationship at the Broadway premiere of "Good Night, and Good Luck." But sadly, the happiness didn't last. Having continually journeyed from France to the United States and vice versa, the couple went their separate ways after just seven months. So what brought this latest chapter of Woodley's love life to an end?

Well, several days later, an insider claimed to People that there hadn't been any animosity. "There is no drama, or hard feelings," the source claimed. "They just have different priorities." However, Woodley sparked rumors that her split from Bravo hadn't been as amicable as first thought when she deleted every photo of the pair together from her Instagram account.