Celebrities You Never Knew Secretly Dated

Not all Hollywood romances are a public affair. Without show-stopping red carpet appearances or catchy No. 1 hits, some relationships don't even make the pages of supermarket tabloids. That said, there are quite a few A-list couples even the biggest Tinseltown junkies don't know about. Read on to learn all about the celebrity pairings that flew under the radar.

Justin Timberlake and Jenna Dewan Tatum

After the "SexyBack" singer's high-profile relationship with pop star Britney Spears, Justin Timberlake reportedly got together with *NSYNC backup dancer Jenna Dewan Tatum. Tatum confirmed rumors of their relationship during an appearance on Bravo's Watch What Happens Live, though she noted that they weren't a couple for long. "We were like friends...that then dated," she said. "We're just really good friends now."

While Tatum didn't divulge many details about their short-lived romance, she did assert that she was not a "rebound," noting, "It's not as salacious as everyone thinks."

Nick Cannon and Kim Kardashian

Before she locked down rapper Kanye West, social media star Kim Kardashian had eyes for Nick Cannon. Fresh from his roles in Drumline (2002) and Love Don't Cost a Thing (2003), Cannon dated Kardashian from September 2006 to January 2007, according to the Daily Mail

The relationship was short-lived because Kardashian kept one major secret from her then-beau: her now-infamous sex tape. "This was my issue. We talked about this tape... And she told me there was no tape," Cannon told The Howard Stern Show in December 2012. "If she might have been honest with me I might have tried to hold her down and be like 'That was before me' because she is a great girl."

Ryan Reynolds and Melissa Joan Hart

Any Sabrina the Teenage Witch fans out there? Fans of the 1996 TV movie may remember seeing Ryan Reynolds playing the floppy-haired love interest to Melissa Joan Hart's eponymous character. However, what many didn't realize was that Reynolds was also vying for Hart's affection behind the scenes.  

While the pair didn't exactly date—Hart had a boyfriend at the time—they got awfully close. In her 2013 memoir, Melissa Explains It All: Tales from My Abnormally Normal Life, Hart says she dramatically landed "a big, fat kiss" on Reynolds after opening an expensive gift he'd given her when filming wrapped (via E! News.) Afterward, the two headed to her hotel room, where Hart said they "fooled around."

Hart supposedly decided to stick with her then-boyfriend, despite Reynolds allegedly wanting something more (via People.)

Ashton Kutcher and January Jones

While Ashton Kutcher seems meant to be with his wife and former That '70s Show (1998-2006) co-star Mila Kunis, he'd first tried his hand at love with actress January Jones. Apparently, that romance didn't play out too well. 

"The guy I was dating when I first got to L.A. was not supportive of my acting," Jones told GQ in a 2009 interview. "He was like, I don't think you're going to be good at this."

Jones said her ex's rude behavior may have been just what she needed to push herself even harder toward finding success in the entertainment industry. "Because the minute you tell me I can't do something, that's when I'm most motivated," said the Mad Men (2007-15) star.

While Jones never named Kutcher directly, GQ's writer put two and two together—and during an appearance on Watch What Happens Live, Jones gave a knowing smile when asked to confirm if Kutcher was indeed the ex-boyfriend in question.

Madonna and Tupac Shakur

While most people remember Madonna's relationships with Michael Jackson, Sean Penn, and Guy Ritchie, many fail to realize that she also dated another superstar—the late rapper Tupac Shakur. Speaking to radio host Stern in March 2015 (via the Daily Mail), Madonna confirmed that she and Shakur hooked up after meeting at the Soul Train Music Awards in March 1993. Shakur clearly had an effect on the "Like a Virgin" singer.

Explaining her infamous 1994 interview with David Letterman, during which she dropped the f-bomb and gave the comedian her underwear, Madonna said she hadn't been mad at Letterman like many believed. Instead, she was simply in a "weird mood." She said, "I was dating Tupac Shakur at the time and the thing is, he got me all riled up about life in general."

While the details of their romance remain under wraps, it was revealed in an old letter obtained by TMZ that Shakur had allegedly called things off because of their different races. "For you to be seen with a black man wouldn't in any way jeopardize your career, if anything it would make you seem that much more open and exciting," he reportedly wrote to Madonna while serving time behind bars for sexually abusing a fan. "But for me at least in my previous perception I felt due to my 'image' I would be letting down half of the people who made me what I thought I was."

Drew Barrymore and Christian Bale

Before he donned a black cape as Batman in the 2005 film Batman Begins, Christian Bale was once just a teenage boy looking for love...or, at least, looking to go on some fun dates. Given his child star status, he didn't just head to a local fast food joint with a girl from school—he went out with Hollywood royalty Drew Barrymore. Unfortunately for Bale, who was 13 years old at the time, the date didn't exactly leave the two feeling weak in the knees.

"We went to see some bloody awful horror film, and that was the end of it," Bale recounted in a 2012 interview with GQ. "She never called again."

Barrymore's excuse for bolting? Apparently, she just wasn't super "boy-crazy" at the time. "I had a lot of fish to fry," she told host Andy Cohen on Watch What Happens Live. "Like, I had big problems in my world for many years... Boys was like very secondary."

Barrymore entered rehab for alcohol and cocaine abuse at just 13 years old, so it makes complete sense that the E.T. (1982) star would pass on puppy-dog love with Bale.

Natalie Portman and Moby

Back in the day, this DJ romanced none other than Black Swan (2010) star Natalie Portman. While not much is known about this odd pairing, Moby (real name Richard Melville Hall) opened up to Spin about his relationship with the actress, admitting that while it may have bolstered his status, it also inspired some hate from Star Wars fans–Portman played Padmé in Episodes I, II, and III.

"I guess in some people's eyes, [nerds] might be mildly sexy—and, as a nerd, I'm certainly happy to enjoy some of the effects of that—but as far as the very brief affair I had with Natalie, it's made me the target of a lot of nerd wrath," he told the magazine. "You can't date Luke Skywalker's mom and not have them hate your guts."

Kristen Bell and Matthew Morrison

It's difficult to imagine Kristen Bell with anyone but her hilarious husband, actor Dax Shepard. But, back in her university days, the Veronica Mars (2004-07) star once dated another actor, Matthew Morrison of Glee (2009-15). Given that Bell is a fan of the hit musical comedy, it seems that the two left things on good terms.

"I actually went to college with Matty Morrison," she told Us Weekly in September 2010. "We actually dated very briefly, so I'll have to say maybe Matt Morrison is my favorite part of Glee for various reasons."

It's nice to know that not all celeb affairs end badly!

Tom Cruise and Cher

Despite being 16 years the singer's junior, action star Tom Cruise once reportedly enjoyed a love affair with Cher in the early 1980s, when his acting career was just starting to take off. While no one would have pegged these two as lovebirds, Cher once said that she felt deeply for Cruise. 

During an interview with Oprah Winfrey in 2008, Cher said (via the Daily Mail), "It could have been a great big romance because I was crazy for him."

A few years later, Cher gave fans a little more insight into her surprising fling. During an appearance on Watch What Happens Live, she told Cohen that Cruise ranked within her "top five" list of best lovers.

Hilary Duff and Shia LaBeouf

Both Hilary Duff and Shia LaBeouf were popular Disney Channel stars back in the day, so while they appear nothing alike today, it's not impossible to imagine these two together. However, the Lizzie McGuire (2001-04) star and the Even Stevens (2000-03) actor just never clicked.

Discussing his past relationships in a 2011 interview with Details (via Us Weekly), LaBeouf revealed that his date with the "So Yesterday" singer did not go well. In fact, LaBeouf said it was "probably the worst date either of us have ever had." Yikes.

Ashley Olsen and Lance Armstrong

After leaving behind her days as an actress in popular straight-to-video movies, Ashley Olsen skirted the spotlight and played her personal cards close to her chest. It's no wonder few realize she dated disgraced cyclist Lance Armstrong. Their relationship wasn't even revealed until the release of the Tour de France champ's 2014 tell-all, Cycle of Lies.

In the book, author Juliet Macur writes (via Radar Online) about Armstrong's romance with Olsen, revealing that the head of Armstrong's nonprofit, the Livestrong Foundation, had "warned the thirty-six-year-old father of three that his May-December romance could damage his cancer work."

In response, Armstrong allegedly said, "She's twenty-one... F**k you."

Strong words. It sounds like Armstrong really fell for the Full House star... if only for a few months.