Maitland Ward has claimed that she hooked up with a mainstream actress after she slide into her DMs.
But based on the mostly short-lived romances of actors, it seems that maintaining a relationship in Hollywood is somewhat difficult. In fact, there are a number of low-profile duos that managed to fly under the radar…
Jared Leto and Cameron Diaz…
Before Leto gained fame in movies such as Suicide Squad and Dallas Buyers Club, he was best known for his work on My So-Called Life and for fronting the band Thirty Seconds to Mars.
He and Diaz dated from 1999 to 2003.
Who we all know from such classics as The Mask, Charlie’s Angels, and My Best Friend’s Wedding.
Justin Timberlake and Cameron Diaz…
Shortly after her breakup with Leto, Diaz met Timberlake at the Nickelodeon Kids’ Choice Awards in 2003.
They began dating soon after, and ended their relationship in January of 2007.
Any recollection of these 2?
Josh Groban and January Jones…
Jones is best known for playing Betty Francis/Draper on the hit show Mad Men.
She dated singer-songwriter Groban from 2003 to 2006.
The relationship ended when Jones stated the 2 were “taking a break.”
Husdon and professional baseball player Rodriguez dated for 4 months.
They ended up splitting in December of 2009.
The pair dated in the early 2000s and even became engaged in 2003, but eventually ended things because Kidman reportedly “wasn’t ready.”
Kidman would go on to star in HBO’s hit miniseries Big Little Lies with Kravitz’s daughter, Zoë, in 2017.
Moby and Natalie Portman…
The Oscar-winning actress dated the musician for a few months in 2001. Moby described the pairing as nothing more than “a brief affair.”
Kim Kardashian and Nick Cannon…
Before she was a household name, Kim Kardashian dated the America’s Got Talent host from September 2006 to January 2007.
Cannon allegedly ended the relationship over Kim’s infamous s*x tape with singer Ray J.
That’s gotta hurt! Although honestly, we bet he’s regretting that now…
Kim Kardashian and Nick Lachey…
Speaking of Kim K, she also briefly dated Jessica Simpson’s ex in 2006. However, Lachey has made statements hinting that she may have just used him for fame.
The duo began dating in the mid-’80s, but ended their courtship after seven years together in 1991.
Downey Jr. later told Howard Stern that the breakup was due to his struggles with addiction.
Matthew McConaughey and Sandra Bullock…
The pair dated after working together on the 1996 film A Time to Kill.
They split up in 1998, but McConaughey only had nice things to say about his ex.
“She’s not a little girl. She’s a woman. She could run a country,” he told Playboy.
The 2 met on the set of Murder by Numbers, which was released in 2002, and split up in 2003.
Maybe it was the sixteen-year age difference?
The actor and the Grammy-winning singer dated from 1999 until 2001.
Crow would then go on to date Lance Armstrong in 2003.
Winona Ryder and Matt Damon…
The Good Will Hunting star dated Ryder for 2 years, and the 2 even shared a house in Beverly Hills.
Ashton Kutcher and January Jones…
Here’s another surprising couple featuring the Mad Men star.
Jones and Kutcher 2 dated from 1998 to 2001, and after the split, Jones claimed that he was a less than a stellar boyfriend.
“He was not supportive of my acting,” she said to GQ in 2009.
“He said, ‘I don’t think you’re going to be good at this.'”
She did add, though, that she should probably thank him, “Because the minute you tell me I can’t do something, that’s when I’m most motivated.”
Cara Delevingne and Michelle Rodriguez…
The Fast & Furious actress and model dated for a few months back in 2014.
Rodriguez described herself as a “lone wolf” in an interview with Interview Magazine…
And she went on to say that her independent personality often leads to breakups.
Jake Gyllenhaal and Kirsten Dunst…
The 2 actors first got together in 2002, purchased a home together, and adopted a dog named Atticus.
They split up after 2 years in 2004. Â
But that weird picture of him watching her eat a salad will live forever!
Kate Bosworth and Orlando Bloom…
After dating for 2 years, the couple ended things in 2006.
Bosworth is now married to director Michael Polish.
While Bloom has been dating Katy Perry since 2016 – and the pair recently became parents!
Wilmer Valderrama and Mandy Moore…
The star of That ’70s Show first began dating Moore in 2001, and their year-long romance ended in 2002.
Years later, Valderrama made crude comments about their s*x life while on the Howard Stern Show.
Not cool, man!
Wilmer Valderrama and Lindsay Lohan…
Speaking of Valderrama, he also dated Lohan in the early 2000s.
They kept their relationship a secret until Lohan’s eighteenth birthday.
And publicly came out as a couple in 2004 only to break up later that same year.
Jessica Biel and Chris Evans…
The Captain America star and The Sinner actress were together on and off for 5 years.
They first got together as Biel was finishing her last season of 7th Heaven.
While it’s not confirmed why they ended things, their last photo taken together was in April of 2006.
Brad Pitt and Gwyneth Paltrow…
After playing husband and wife in the psychological thriller Se7en, the 2 started dating in 1995.
They eventually became engaged.
But they broke their engagement shortly afterward, and Paltrow told Howard Stern, “I wasn’t ready and he was too good for me.”
Ryan Reynolds and Alanis Morrisette…
The Canadian singer and actor met in 2001 and dated for 5 years.
While they ended up getting engaged, they called things off in 2006.
Reynolds is now one part of the internet’s favorite couple, alongside actress Blake Lively!
Clooney and Liu had a very brief, relatively unknown fling, in 2000.
While it didn’t last long, they were each other’s new year’s kiss for the new Millenium.
Jake Gyllenhaal and Reese Witherspoon…
Witherspoon started dating Gyllenhaal shortly after her split from ex-husband Ryan Phillippe in 2007.
They first met on the set of their film Rendition, and were together until 2009.
This relationship totally passed us by!
Cher and Tom Cruise…
Yep. This happened. The 2 had a brief fling in the ’80s, and Cher was even quoted once as saying that Cruise was one of her “top five favorite lovers.” Go, Tom!
Maitland Ward and ?
The actress is best known for her role as Rachel McGuire on Boy Meets World, but since then has become a verified adult movie sensation.
But in her new tell-all book, she claims she had a fling with “a mainstream actress people would probably know.”
“I had an attraction to her when I saw it, so it was surprising. I was pleasantly surprised that time,” Ward teased.
“With her, I was excited because I did actually meet up with her and there’s a whole story with that, so that was more of an organic kind of thing I guess.
“It didn’t end well, but still, that was different!” she said.
Now the whole internet has just one question… Who?