Relationships

20 Shocking Celebrity Flings You Totally Forgot Happened

It's safe to say 2019 was a big year for surprising celebrity relationships. Notable reported flings included Miley Cyrus and Kaitlynn Carter, Tyler Cameron and Gigi Hadid, and Pete Davidson and Kate Beckinsale. (It's been a long year.) Those three storylines were juicy enough to keep fans thoroughly invested for months. But as dramatic as they were, they barely hold a candle to some of the most shocking celebrity flings of the past two decades. These romances didn’t last long, but they won’t soon be forgotten in pop culture lore.

Here’s a look back at some reported celebrity pairings you probably haven’t thought about in hot minute. Some of these reported couples met on the set of movies or other projects they worked on together. Some of them ended in drama, and other reported couples still remain friends to this day. The one thing these reported relationships all have in common? Everyone in them has moved on with other people, some of them are now parents, and others are thriving on their own and living their best lives. Please enjoy this trip down memory lane as you recall the most surprising relationships of the '00s and '10s. Who knows what the '20s will bring? (I do. Me and Harry Styles. Just putting it out into the universe! Repeat after me: Manifesting.)

Ian West - PA Images/PA Images/Getty Images
Relationships — 20 Shocking Celebrity Flings You Totally Forgot Happened

2002: Jenna Dewan & Justin Timberlake

Before Jenna Dewan married Channing Tatum, she was a backup dancer for Justin Timberlake. The two dated briefly after Timberlake’s breakup with Britney Spears. Dewan confirmed this in 2017 on Andy Cohen’s Watch What Happens Live, saying, “[It was] not that long. We were friends. Then we dated.”

Frank Micelotta Archive/Getty Images Entertainment/Getty Images

2005: Maria Sharapova & Adam Levine

Adam Levine and Maria Sharapova reportedly first met at Sharapova’s birthday party, and reportedly had a brief fling. Things got messy after it ended, when Russian magazine Exile published a story claiming Levine made derogatory comments about his sex life with Sharapova. Levine denied saying this and threatened legal action against the publication. Elite Daily reached out to representatives for both Levine and Sharapova for confirmation on their reported relationship, but did not hear back by the time of publication.

Theo Wargo/WireImage/Getty Images

2007: Megan Fox & Shia LaBeouf

Back when they co-starred as romantic leads on Transformers, Shia LaBeouf and Megan Fox had offscreen chemistry as well. On their relationship, Fox told Andy Cohen in 2018, “I would confirm that it was romantic. I love him. I have never been really quiet about that. I love him.”

Christian JENTZ/Gamma-Rapho/Getty Images

2007: Ashley Olsen & Lance Armstrong

Ashley Olsen reportedly dated former cyclist Lance Armstrong for a few short months, back before his infamous doping scandal. A 2014 book by Juliet Macur about Armstrong claimed that a friend “warned” him that the “May-December romance could damage his cancer work." Elite Daily reached out to representatives for both Olsen and Armstrong for confirmation on their reported relationship, but did not hear back by the time of publication.

Brian ZAK/Gamma-Rapho/Getty Images

2007: John Mayer & Jessica Simpson

John Mayer and Jessica Simpson's relationship is mostly known for the explicit comments Mayer made about Simpson in a Playboy interview in 2010, years after their breakup. He called her “sexual napalm” and likened their relationship to a drug addiction. Simpson told Oprah Winfrey that Mayer’s comments “disappointed” her.

L. Cohen/WireImage/Getty Images

2008: Drew Barrymore & Ed Westwick

Drew Barrymore and Ed Westwick shook fans in September 2008 when photos of them making out at a Saturday Night Live after party in New York City went public. According to an Us Weekly source at the time, they had reportedly hooked up at least one time before that. Elite Daily reached out to representatives for both Barrymore and Westwick for confirmation on their reported involvement, but did not hear back by the time of publication.

Patrick McMullan/Patrick McMullan/Getty Images

2008 to 2009: Lindsay Lohan & Samantha Ronson

Lindsay Lohan and Samantha Ronson dated on-and-off for about a year before they broke things off for good in 2009. Lohan told Howard Stern in January 2019 the two were “more friends than anything.”

Mark Milan/Mu Kei/GC Images/Getty Images

2009: Katy Perry & Josh Groban

Katy Perry and Josh Groban reportedly dated in 2009, and the short relationship seems to have left a lasting impression. Perry’s hit single, “The One That Got Away,” was actually written about Groban, she confirmed to James Corden in 2017.

NBC NewsWire/NBCUniversal/Getty Images

2009: Taylor Swift & Taylor Lautner

Ah, yes. Taylor Squared. These two reportedly first met on the set of the movie Valentine's Day and dated briefly in 2009. In 2016, Lautner told Scream Queens co-stars Lea Michele and John Stamos that Swift's song “Back To December" was about him.

Jean Baptiste Lacroix/WireImage/Getty Images

2010: Aubrey Plaza & Michael Cera

OK, so this was more than just a fling, but the two comedians kept their relationship seriously under wraps. In 2016, Aubrey Plaza revealed that she and Michael Cera dated for “a year and a half” when they were filming Scott Pilgrim vs. the World in 2010. She even said they "almost got married in Vegas.”

Jeff Kravitz/FilmMagic, Inc/Getty Images

2010: Chelsea Handler & 50 Cent

Chelsea Handler and 50 Cent (whose real name is Curtis Jackson) met in 2009 on Handler’s late-night show, Chelsea Lately, then dated “very casually,” according to Handler. They seem to have remained friendly, seeing as 50 posted a funny birthday tribute to his ex in 2016.

Bravo/NBCUniversal/Getty Images

2011: Blake Lively & Leonardo DeCaprio

Back in her Gossip Girl days, Blake Lively reportedly had a brief romance with Leonardo DiCaprio between May and October. They were first spotted hanging out in France and Italy, and things reportedly ended right before Lively started seeing now-husband Ryan Reynolds. Elite Daily reached out to representatives for both Lively and Reynolds for confirmation on their reported romance, but did not hear back by the time of publication.

Gregg DeGuire/FilmMagic/Getty Images

2015: Travis Scott & Rihanna

Travis Scott and Rihanna reportedly first started hanging out during New York Fashion Week in September 2015. Multiple sources reportedly confirmed their relationship to E! News, saying, “It's already very serious. He's very into her." Things reportedly fizzled out after only a month or so. Elite Daily reached out to representatives for both Rihanna and Scott for confirmation on their reported relationship, but did not hear back by the time of publication.

Jean Catuffe/Getty Images Sport/Getty Images

2015: Miley Cyrus & Stella Maxwell

Miley Cyrus was photographed kissing Stella Maxwell, a model and Victoria’s Secret angel, while she and Liam Hemsworth were in one of their “off again” phases. Some fans are convinced that Cyrus’ 2017 song “She’s Not Him” is about her brief reported romance with Maxwell. In 2015, Cyrus told Elle UK she was not dating anyone exclusively. "I'm 22, I'm going on dates, but I change my style every two weeks, let alone who I'm with," she told the magazine. Elite Daily reached out to representatives for both Cyrus and Maxwell for confirmation of their reported involvement, but did not hear back by the time of publication.

picture alliance/picture alliance/Getty Images

2015: Joe Jonas & Gigi Hadid

Joe Jonas and Gigi Hadid were friends for years before reportedly becoming romantically involved in summer 2015. "Gigi feels very comfortable with Joe and it's very easy to talk about everything that's going on in her life with him,” a source reportedly told E! News at the time. “He understands where she is at and they are not in any rush." By the end of the year, they were reportedly over. A source reportedly said, “Their schedules started affecting their relationship.”

Demis Maryannakis/Star Max/GC Images/Getty Images

2015: Jennifer Lawrence & Liam Hemsworth

Jennifer Lawrence and Liam Hemsworth starred in The Hunger Games franchise together, where they shared several steamy moments on screen. Dating rumors surfaced about them when they were spotted out to dinner in October 2015. Lawrence hinted that December that she and Hemsworth had hooked up when she told Andy Cohen, “Liam and I grew up together. Liam’s real hot. What would you have done?”

picture alliance/picture alliance/Getty Images

2015-2016: Kate Hudson & Nick Jonas

Jonas and Hudson reportedly first started seeing each other in September 2015 and were spotted out together multiple times in the months following. In January 2016, Jonas told Complex magazine, "Kate’s incredible. We had an unbelievable connection as two humans who just admire things about each other, and see see something in each other that was beautiful. Out of my best effort to respect her and her privacy, I’m not going to say if we had sex or not. But we did have a beautiful connection. Even now I have so much admiration and respect. She's amazing.”

C Flanigan/Getty Images Entertainment/Getty Images

2015 - 2016: Kendall Jenner & Harry Styles

Harry Styles and Kendall Jenner were first romantically linked in November 2013. At the time, they insisted they were just friends. In 2015, the two were photographed "getting cozy" on vacation in St. Barts. At the time, a source reportedly told Entertainment Tonight “there has been something going on with those two for a while.”

This rumored fling has garnered new attention lately, after Jenner and Styles appeared on an episode of James Corden’s Spill Your Guts Or Fill Your Guts on Dec. 10, 2019. On the segment, Jenner had to ask Styles which of the songs on his last album were about her. She prefaced the question with, "Dying to know this!"

David M. Benett/Getty Images Entertainment/Getty Images

2016: Justin Bieber & Sofia Richie

Sofia Richie and Justin Bieber documented their brief relationship publicly on social media, to the dislike of some of Bieber’s fans. “We have a special relationship,” Richie told Billboard at the time. “Justin is very easy to talk to, and that’s hard to find with people in Los Angeles.” Elite Daily reached out to representatives for both Bieber and Richie for confirmation on their reported relationship, but didn't hear back by the time of publication.

Jun Sato/GC Images/Getty Images

2018: Shawn Mendes & Hailey Baldwin

Shawn Mendes and Hailey Baldwin attended the 2018 Met Gala together, making fans think they were formally making their couple "debut." At the time, Mendes claimed they were just friends, but he has since admitted to Rolling Stone that he and Baldwin were romantically involved. "I don’t even want to put a title on it,” Mendes told the magazine in November 2018. “I think it was more of a zone of limbo."

Feeling nostalgic yet? Years later, I'm still shook over these former couples. May the world never forget just how dramatic these reported relationships were. Onward!

Noam Galai/Getty Images Entertainment/Getty Images
120