Shailene Woodley Boyfriends 2020: Who Is Shailene Dating Now?

For those of us anxiously awaiting the premiere of the new HBO show Big Little Lies (based on the book of the same name by Liane Moriarty), there are plenty of A-list actors and actresses to be excited about seeing. Included in the cast are Reese Witherspoon, Nicole Kidman and Shailene Woodley. Also exciting? Seeing which on-screen romances translate off-screen. This is often a strong possibility especially with an actress like Woodley, who seems to be the queen of dating co-stars.

It’s no secret that the 25-year-old actress has starred alongside several crush-worthy guys in her sizable list of television and movie credits, including Daren Kagasoff (Secret Life of the American Teenager), Theo James (Divergent series) and Ansel Elgort (The Fault in Our Stars). Those three are included in a list of co-stars Woodley has been linked to romantically.

How many of those stars has Woodley actually dated? Who else might she have been with? Despite her claims in previous years to not having time to even think about romantic relationships due to her hectic schedule, she has hinted at the fact that she might have hooked up with a co-star or two post production. With the arsenal of handsome guys she acts along with, it’s no surprise. Let’s take a look at the soon-to-be Big Little Lies star’s dating history.


Daren Kagasoff 2008

Shailene Woodley Daren Kagasoff Dating Secret Life of the American Teenager

Photo by Maury Phillips/Getty Images for GBK Productions

Rumors flew about Woodley possibly dating her Secret Life co-star Daren Kagasoff as soon as the show aired. On-screen, their characters had already hooked up prior to the start of the show. It seems that their chemistry spilled over off-screen.

Though neither officially admitted to dating, Kagasoff confirmed that he had a crush on Woodley, and Woodley has been quoted as saying anyone would be “dead lucky to be with him. I am dead lucky.” However, she challenged the fans to figure out if they were dating or not.

Since then, both have been linked to other actors, including other Secret Life co-stars, and both have said relationships are hard to sustain due to their busy schedules, so if the two ever were together, it can be inferred that they didn’t date for too long.


Miles Teller 2013

Shailene Woodley Miles Teller Movies Dating

Photo by Jason Kempin/Getty Images

Woodley’s first role after Secret Life wrapped was a movie called The Spectacular Now, in which she co-starred alongside Miles Teller. Woodley and Teller played each other’s love interests in the movie and rumors flew about a possible off-screen romance.

Though Teller denied these claims, saying he never dated Woodley, Woodley herself never confirmed or denied the rumors, preferring to keep the fans guessing. Whether or not they dated, the two seem to sustain a working relationship, as they starred together again when they were both cast in Divergent in 2014 and continued to work on the other movies in the series together.


Theo James 2014

Shailene Woodley Theo James Dating Movies Divergent

Photo by Mark Sagliocco/Getty Images

Speaking of Divergent, during Woodley’s time filming that movie, she was linked to dreamy English co-star Theo James. Woodley and James had very convincing chemistry as each other’s love interests and fans wanted to see if that carried over off-screen. Though these two never dated, considering James had a serious girlfriend in Ruth Kearney when they first met, fans were still hopeful for an off-screen romance to bloom.

The last movie in the series, Ascendant, comes out as a TV movie in June of this year, and rumors have been flying since the release of Allegiant in 2016 that James and Kearney, who were engaged for quite a while, may be on the outs, giving fans hope. However, nothing has been confirmed on the status of James and Kearney’s relationship, leaving the status of James and Woodley’s relationship as a question mark.


Ansel Elgort 2014

Shailene Woodley Ansel Elgort movies dating the fault in our stars

Photo by Theo Wargo/Getty Images

2014 was a busy year for Woodley. Her Divergent co-star, Ansel Elgort, who played her brother on the action-thriller, joined Woodley on her next big movie, The Fault In Our Stars. In this film, Woodley and Elgort played the epic on-screen couple of Hazel and Augustus. The Fault In Our Stars first came out as a book by popular author John Green in 2012, giving fans two years to fall in love with the characters and their relationship.

With such a buzz following Hazel and Augustus, it only grew stronger after the movie came out, and it should come as no surprise that rumors of the actors taking their on-screen romance off-screen emerged, with Woodley being linked to James earlier the same year. However, Woodley herself dispelled these rumors, stating that their relationship mirrored that of the one they played in Divergent: brother and sister.


Shiloh Fernandez 2013 – 2014

Shailene Woodley Shiloh Fernandez movie dating sundance

Photo by Ben Gabbe/Getty Images

Woodley starred in one more movie in 2014, a dramatic mystery called White Bird in a Blizzard. Despite already being rumored to be dating both Theo James and Ansel Elgort thanks to the other movies she worked on that same year, speculation about Woodley dating her movie co-star Shiloh Fernandez arose.

When confronted about these claims, Woodley laughed them off, stating how funny it was that people automatically assumed they were dating just because they took photos together. However, the first rumors of Woodley and Fernandez’s possible relationship emerged in 2013, a year prior to the movie’s release, when the two were caught kissing at the Sundance Film Festival.


Ellen Page 2014

Shailene Woodley Ellen Page friends dating pansexual lesbian coming out

Photo by Scott Olson/Getty Images

Although this relationship has never been confirmed, Ellen Page and Shailene Woodley, who have been longtime friends, were rumored to have been in a romantic relationship. Woodley hinted at being pansexual just a few months after Page came out as lesbian, and though it’s speculated this relationship is made up, the rumors were never dispelled either.

Instead of shooting them down, Woodley let the rumors die out on their own when Page was spotted with a different girl on the set of her 2015 movie Freeheld.


Nahko Bear 2014-2016

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don't eat yellow snow. ❄️

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Yet another unconfirmed relationship rumor starts; however, this one has a little more basis than the claims of Woodley dating Theo James or Ellen Page. Since Divergent first came out in 2014, Woodley has been linked to Nahko Bear, frontman of the folk band Nahko and Medicine For The People.

Like Page, Bear is not one of Woodley’s co-stars but seemed to have a large impact on her life. Bear’s band has put out music that Woodley claimed changed her life. In addition, she was in the band’s video for their song “Black as Night,” in which several people are filmed holding up a sign reading “I believe in the good things coming,” which are lyrics from the song.

Woodley, who has always been rather socially conscious, got arrested participating in a protest of one her latest causes, protecting the Dakota Access Pipeline. Bear was rumored to be there with her. The protesters were standing up with the Native Americans in the area. It is speculated that Woodley’s presence there and continued presence there even after she got arrested was due to her relationship with Bear, who is part Apache.

In addition, Woodley has been described as a “hippie” who “eats clay” and wants to date someone who can go along with her hippie, easygoing way of life. Bear fits the bill perfectly.

Bear has been Woodley’s last romantic link, with rumors lasting for two years. This leads to speculation that it is a real relationship. This link has not been severed yet nor has either person dispelled the rumors. However, neither has confirmed a relationship either, meaning Woodley will be linked to other stars, most likely her co-stars in Big Little Lies, and fans are excited to see who she will be with next and whether or not her next rumored romantic partner will ring true.


Ben Volavola 2017

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#BenVolavola #Crusaders

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Rumor has it that Shailene has got herself a new man. According to E! Online, Shailene is dating Austrailian international rugby player Ben Volavola, 26. The two haven’t confirmed or denied anything but Shailene has been posting cryptic Instagram’s with a man and she’s in Austrailia.

https://www.instagram.com/p/BaLITsTlIUL/?taken-by=shailenewoodley

Ben just signed to Austrailia rugby team, Melbourne Rebels. Looks like Shailene has found love while down under.


2018

Shailene Woodley had made her relationship official with a kiss on Instagram with rugby player Ben Volavola.

2019

Shailene Woodley and her rugby player boyfriend Ben Volavola made their relationship Instagram official in January.

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