Skip To Content

    I 100% Forgot About These Celebrity Couples, Which Is Odd Because They're Weird Enough To Be Super Memorable

    I was today years old when I found out Tyra Banks and Drake dated.

    Who doesn't love celebrity couples? I mean, some are simply unforgettable, no matter how long ago they dated.

    Singers Britney Spears and Justin Timberlake in the audience at the 2000 MTV Music Video Awards in New York
    Dave Hogan / Getty Images

    On the other hand, some famous couples just fade into insignificance as if they never existed in the first place!

    CBS

    So prepare yourself for some serious WTF moments as we take a trip down memory lane with these 22 celeb couples we completely forgot dated.

    1. Madonna and Tupac

    Madonna and Tupac Shakur at the Interview Magazine party in 1994 in New York City
    Patrick McMullan / Getty Images

    During an interview with Howard Stern in 2015, Madonna shocked the world by revealing that she once dated Tupac Shakur. The couple were together between 1993 and '95, and in a love letter written by the rapper, he is said to have ended things with the singer because she was white.

    2. Jenna Dewan and Justin Timberlake

    Justin Timberlake and dancer Jenna Dewan performing at the 44th Annual Grammy Awards
    Frank Micelotta Archive / Getty Images

    After his split from Britney Spears in 2002, Justin moved on with Jenna, his backup dancer. The dancer dropped the bomb that they dated during an interview on Watch What Happens Live With Andy Cohen, but Jenna was adamant that she wasn't a rebound. I'm no detective, but looking at the timeline, it kinda seems like she was! Never mind, let me go back to minding my own business, chile.

    3. Macaulay Culkin and Mila Kunis

    Macaulay Culkin and Mila Kunis smiling at the launch of the "uBid for Hurricane Relief" charity auction and benefit at the Empire Ballroom
    Ethan Miller / Getty Images

    Mila and Macaulay were together between 2002 and 2011, and they met when she was 18 and he was 21. After the pair split, Mila made an appearance on Dax Shepard’s podcast, Armchair Expert, admitting that her behaviour during the breakup was "terrible". She never went into any more detail, though!

    4. Lenny Kravitz and Nicole Kidman

    Lenny Kravitz and Nicole Kidman embrace in the green room during the Hollywood Film Awards
    Charley Gallay / Getty Images

    I can't be the only one who didn't anticipate this AT ALL, but Nicole and Lenny were, in fact, in a relationship between the years 2003 and 2005. They were even engaged! The couple called it quits after a few years of dating, but there were no hard feelings, with Nicole expressing in an interview with the Edit that she had nothing but love for the musician.

    Apparently, Nicole's Big Little Lies costar Zoë Kravitz is also a big fan of hers: "I was about 13, and she would take me to see movies; she was so nice to me."

    5. Jared Leto and Cameron Diaz

    Jared Leto and Cameron Diaz are pictured sitting together
    Jeff Kravitz / FilmMagic / Getty Images

    In the early 2000s, Cameron and Jared were the talk of the tabloids even though they tried to keep their relationship under wraps. They began secretly dating in 1999 and were together for four years before calling it quits in 2003.

    6. Zachary Quinto and Jonathan Groff

    Zachary Quinto and Jonathan Groff pose backstage at the hit musical "Hamilton" on Broadway at the Richard Rogers Theater
    Bruce Glikas / FilmMagic / Getty Images

    Zachary and Jonathan began dating in 2010 and spilt in 2013 due to difficulties maintaining a long-distance relationship. They remain friends and even reunited at Jonathan's Broadway show Hamilton. Nothing but friendly exes over here!

    7. Courteney Cox and Michael Keaton

    Michael Keaton and Courteney Cox
    Steve Granitz / WireImage / Getty Images

    In 1989, Courteney met Michael after expressing to a mutual friend how much she liked his performance in the film Clean and Sober. The pair were together for six years before they called it quits in '95. A few months later, in an interview with People magazine, Courteney claimed that there was no bad blood between them, praising the actor for being "the most wonderful person I've ever met."

    8. Michael Sheen and Rachel McAdams

    Rachel McAdams and Michael Sheen at the "Sleeping Beauty" premiere during the 64th Annual Cannes Film Festival
    Andreas Rentz / Getty Images

    These two met on the set of Midnight In Paris and would later debut their romance at the 2011 Cannes Film Festival. Reportedly, they later split because Rachel wanted to settle down and start a family, but Michael had already been married and had a child, so he wanted to focus more on his career.

    9. Nick Cannon and Kim Kardashian

    Nick Cannon and Kim Kardashian posing for a picture together
    Johnny Nunez / WireImage / Getty Images

    Before Kim shot to fame, she dated Nick between 2006 and 2007, but when her infamous sex tape was leaked, her relationship with Nick ended. In a 2012 Howard Stern Interview, Nick revealed that they broke up because Kim lied to him about the existence of the tape. Nick added that it might've worked out if she didn't "break his heart".

    10. Sarah Jessica Parker and Robert Downey Jr.

    Actress Sarah Jessica Parker and actor Robert Downey, Jr. attend the 1988 Presidential Campaign
    Ron Galella Ltd. / Getty Images

    Yes, you heard that right. After meeting on the set of the film Firstborn in 1984, Sarah and Robert began a relationship that lasted eight years but would slowly crumble due to Robert's spiralling addiction to drugs. Reflecting on their relationship on the WTF podcast interview, Sarah expressed that she fell out of love with Robert and only stayed because she "didn't want him to die".

    11. Ryan Gosling and Sandra Bullock

    Sandra Bullock poses with Ryan Gosling as they arrive at the Palais des festivals
    Francois Guillot /AFP / Getty Images

    I guess many people think of Rachel McAdams when they imagine Ryan's dating history, but let's TBT his days with Sandy! The two met on the set of Murder by Numbers and dated for about a year. Ryan later told Us magazine that Hollywood was to blame for their breakup, calling show business "the bad guy". Regardless, he still praised the actor for being one of his best girlfriends ever.

    12. Jessica Biel and Chris Evans

    Jessica Biel and Chris Evans pose together
    Gregg Deguire / WireImage / Getty Images

    Can we get into this couple for a moment, please?! Jessica and Chris started dating in 2001 and would go on to costar in the movies Cellular and London before eventually splitting in 2006 after five years together.

    13. Nathan Sykes and Ariana Grande

    Ariana Grande performs with Nathan Sykes of the Wanted on "Live With Kelly and Michael"
    David Steele / Disney General Entertainment Content / Getty Images

    Ariana and Nathan first met when they collaborated on the song "Almost Is Never Enough", and I meannnnnn, THE CHEMISTRY! The couple dated for five months and ended their relationship in December 2013 due to issues related to being in a long-distance situation. Nevertheless, they remained friends and even recorded another song together, entitled "Over and Over Again", for Nathan's debut solo album.

    14. Taylor Swift and Joe Jonas

    Taylor Swift and Joe Jonas at the 2008 MTV Video Music Awards
    Jeff Kravitz / FilmMagic / Getty Images

    Even though Taylor and Joe only dated for three months back in 2008, they managed to split up in a pretty bitter way. The Grammy winner put Joe on blast on The Ellen DeGeneres Show, saying he dumped her via a 27-second phone call. In a later interview with Us magazine, Taylor said they spilt because actor Camilla Belle sabotaged their relationship. The two have moved on, though, and are now friends. They even managed to see the funny side of things!

    15. Tyra Banks and Drake

    Tyra Banks and Drake attend the Flawsome Ball
    Paul Bruinooge / Patrick McMullan / Getty Images

    Tyra had one date with Drake back in 2012, during which they went to Disneyland in disguise. Drake revealed on The Ellen DeGeneres Show that he didn't know if it was a date per se and that the pair are still friends; Tyra even appeared in Drake's 2016 video for "Child's Play" as his love interest!

    16. Vanessa Hudgens and Josh Hutcherson

    Vanessa Hudgens and Josh Hutcherson smiling at the world premiere of "Journey 2: The Mysterious Island" at Village Cinemas Jam Factory
    Graham Denholm / Getty Images

    Vanessa and Josh met on the set of Journey 2: The Mysterious Island and enjoyed a short-lived romance without anyone knowing at the time! It wasn't until they broke up that it was revealed the pair had even dated. Josh would later joke on the Today show that Vanessa "broke his heart".

    17. Janet Jackson and Matthew McConaughey

    Janet Jackson and Matthew McConaughey at the 44th Annual Grammy Awards at the Staples Center in Los Angeles
    Frank Micelotta Archive / Getty Images

    Janet and Matthew met at the Grammys in 2002, and though there were rumours back then that they were dating, neither of them ever confirmed it. However, in a 2006 interview with Upscale magazine, Janet would admit that they briefly went out, but "just for a minute". Matthew also confirmed this in 2019 on Watch What Happens Live, confessing that they had gone on one dinner date together and "that was sorta it". I guess that's the way love goes, right?

    18. Paul Rudd and Jennifer Aniston

    Jennifer Aniston and Paul Rudd attend the premiere of "The Object Of My Affection" at GCC Avco Theater in Westwood
    Michael Ochs Archives / Getty Images

    These two briefly dated while filming The Object of My Affection back in 1998. Even though it was a short-lived affair, they have remained good ~friends~ and even reunited to play a married couple in the 2012 movie Wanderlust. Also, Jen posted a super-sweet Instagram story dedicated to the star, who was named People magazine's Sexist Man Alive last year, which I think is just awesome behaviour!

    Here's the post for you here:

    A picture taken from Jennifer Aniston's Instagram story showing a screenshot of Paul Rudd and saying she's always known he's the sexiest man alive
    Jennifer Aniston / Via Instagram

    19. Cher and Tom Cruise

    Tom Cruise and Cher in the 1980s
    Rex Shutterstock / Getty Images

    This is...an interesting pairing, but yes, it happened! In 1985, Cher and Tom met at Madonna and Sean Penn's wedding in Malibu, California, but they wouldn't connect properly until they met at the White House years later. It's not clear why they broke up, but what we do know is the pair enjoyed a short romance. In 2013, Cher would appear on Watch What Happens Live With Andy Cohen and rank Tom as one of her top five lovers!

    20. Miley Cyrus and Nick Jonas

    Miley Cyrus and Nick Jonas of Jonas Brothers perform at New Cowboys Stadium
    Rob Hoffman / Getty Images

    I guess this is a Disney love story? A phrase like that would be fitting, since Nick and Miley fell for each other when they were just 13 years old. They dated for a year, splitting up in December 2007. Even though the pair have never addressed why they broke up, Miley's song "7 Things" is rumoured to be about Nick. In fact, in 2021 Miley celebrated the anniversary of the hit song by tagging him in a social media post, proving that despite their deep heartbreak, they're all gravy.

    Here's a clip from the Jonas Brothers documentary Chasing Happiness:

    21. Sinitta and Brad Pitt

    Brad Pitt kissing Sinitta on the cheek while she smiles happily
    Alpha Press / Getty Images

    I gotta be honest — this is easily one of the most bizarre Hollywood relationships I've heard of! Brad and Sinitta started dating back in the '80s, and in an interview with OK magazine, the singer explained that they broke up in 1988 due to long distance. Sinitta certainly did her best to make it work, and who can blame her? She allegedly spent a fortune calling Brad and sending him 40-page faxes, but her efforts weren't reciprocated, and the relationship fizzled out. 

    Are there any other random forgotten celeb couples we missed? Let us know in the comments below!