I Forgot About These Celebrity Couples, Which Is Odd Because They Weird Enough To Be Memorable

During an interview with Howard Stern in 2015, Madonna shocked the world by revealing that she once dated rapper Tupac. 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.

After his split with Britney Spears in 2002, Justin moved on with his backup dancer Jenna Dewan. 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.

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

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 co-star 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”.

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.

Zachary and Johnathan began dating in 2010 and later spilt in 2013 due to the difficulties they were having maintaining a long-distance relationship. They still remain friends, and even reunited at Jonathan’s Broadway show, Hamilton. Nothing but friendly exes over here!

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.”

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, meanwhile Michael had already been married and had a child, so he wanted to focus more on his career.

Before Kim shot to fame, she dated Nick Cannon 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”.

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”.

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 break-up, calling show-business “the bad guy.” Regardless, he still praised the actor for being one of his best girlfriends ever.

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

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 around being in a long distance situation. Nevertheless, they still remained friends, and even recorded another song together entitled “Over and Over Again” for Nathan’s debut solo album.

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 via a 27 second phone call. In a later interview with US magazine, Taylor said they spilt because actress Camilla Belle sabotaged their relationship. The two are now friends though, and have moved on and even managed to see the funny side of things!

Tyra had one date with Drake back in 2012, for which they went to Disneyland in disguise. Drake revealed on The Ellen 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!

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 even dated each other. Josh would later joke on The Today Show that Vanessa “broke his heart”.

Janet and Matthew met at the Grammy’s 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?

These two briefly dated whilst 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 the Sexist Man Alive last year, which I think is just awesome behaviour!

This is… An interesting pairing, but yes, it happened! In 1985, Cher and Tom met at Madonna and Sean Penn’s wedding in Malibu, 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!

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.

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.