Celebrity Relationships That Everyone's Moved On From But Still Live Rent Free In My Head

As someone born in '97, I'll never get over the early '90s couples I missed out on!

Do you ever think about a celebrity relationship and come to that moment of "did that actually happen or was I having some kind of fever dream?" or "damn, I forgot about them; I hate that they didn't work out."

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Well, if so, here are some celebrity relationships that we as a society have decided to push from our minds but still continue to live rent free in my head:

1. Cher and Tom Cruise

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Nothing is wilder than the free, disco-loving icon that is Cher being with such an interesting man as Tom Cruise. Cher and Tom really dated back in the '80s. They met at Madonna and Sean Penn's wedding in 1985 and then later reconnected at a White House event that same year, and eventually sparked their romance.

They eventually broke up due to the difficulty of maneuvering such busy schedules. Actually, back in 2013, on an episode of Bravo's Watch What Happens Live, Cher told host Andy Cohen that Tom was one of her top five lovers. She also made sure to let us know, "He wasn't a Scientologist then! It was pretty hot and heavy for a little minute." 

2. Selena Gomez and The Weeknd (Abel Tesfaye)

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This is one of those things where you just had to be there. Between the songs, Selena's kidney transplant, and the love triangle/square, you literally couldn't even make this up. Beliebers, Selenators, hip-hop fans, and fashion fans were all enamored with this whole situation. Back in 2015, Selena and Abel reportedly met at the Victoria's Secret fashion show when she had just gotten back with Justin Bieber, and Abel was with his on-again, off-again girlfriend, Bella Hadid.

By January 2017, Selena and Abel were Instagram official, and after ten months of constant publicity and Beliebers being unable to let go of "Jelena," they "amicably" broke up in October 2017. She eventually reunited with Justin (for the last time), and Abel went on to later date one of Selena AND Bella Hadid's best friends and later continued his on-again, off-again relationship with Bella. Honestly, it was always Abel and Bella for me. 

3. Jeanette McCurdy and Andre Drummond

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Random doesn't even begin to describe how shocked I was when I found out Jeanette McCurdy was flirting on social media with NBA player Andre Drummond. It felt like one of those things we all collectively blocked out of our brains because it was SO left-field.

It all started in 2013 when Andre would make flirtatious Twitter posts about Jeanette (like making her his "Woman Crush Wednesday"). After finally noticing (and doing her research on him), Jeanette decided to indulge and eventually planned to meet up with him in LA over Labor Day. They met, sparks flew, and thus bloomed their week-long relationship.

4. Angelina Jolie and Billy Bob Thornton

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Before we had Machine Gun Kelly and Megan Fox drinking each other's blood, we had Angelina Jolie, Billy Bob Thornton, and the blood-smeared lockets. Back in 1999, Angelina and Billy (who was with actress Laura Dern at the time) met each other on the set of the movie Pushing Tin. Angelina and Billy ended up eloping the following year in Las Vegas. Back in 2000, Laura Dern told Talk magazine, "I left our home to work on a movie, and while I was away, my boyfriend got married, and I've never heard from him again."

The relationship between Billy and Angelina had an actual PRIMAL passion to it; it was wild. By 2001, they were wearing lockets smeared with the other's blood on the inside, and by 2002, they were looking to adopt their son, Maddox. Unfortunately, their marriage ended that same year, and Angelina received full custody of Maddox. However, friendship isn't dead, because in 2022, Billy's son Harry (from a marriage before Angelina) told Entertainment Tonight that Angelina still sends him a Christmas present every year. 

5. Rihanna and Hassan Jameel

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This relationship BROKE the internet. When those pictures of Rihanna and Hassan (a VERY wealthy Saudi businessman) leaked back in June 2017, it sent the internet into total shambles (especially when everyone found out how rich he was). People were trying to figure out who this gorgeous man Rihanna had popped out with was. Remember, this is also the time when everyone (including me) was still trying to figure out what exactly happened between Drake and Rihanna.

Regardless, Hassan was precisely the content we wanted for her. It seemed he really cared for her, truly made her happy, and it was giving this is a MAN, not a boy. Unfortunately, after giving us nearly three years of some of the most visually pleasing content to meet the eye, in January 2020 (the year from hell), Rihanna and Hassan broke up due to their lives being too different and it being too difficult to maintain their relationship.

6. Bill Murray and Kelis

Children of Zeus x Kelis x Bill Murray type beat pic.twitter.com/iYcxxBubE3

— Children of Zeus (@ChildrenOfZeus) May 30, 2023

@ChildrenOfZeus / Via Twitter: @ChildrenOfZeus

Yeah, I didn't know the boys that Kelis' milkshake brought to the yard meant Bill Murray. No one could have EVER prepared me for how bizarre we were going to get in 2023. Six-year-old me would have never imagined that 26-year-old me was going to see a ghostbuster and the milkshake lady in the same picture, let alone in a relationship.

Earlier this year, Bill was spotted at not one but TWO music festivals that Kelis was performing at. The two were also seen close backstage AND in photographs together. Unfortunately, just two months after the reported dating, reports came that they had broken up. I still can't believe it.

7. Reese Witherspoon and Ryan Phillippe

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I just KNEW after I saw Cruel Intentions for the first time that this was it for me. Unfortunately, by the time I was old enough to watch and understand the movie, they had already divorced. Imagine my utter heartbreak. How much better of a trope could you get?! Teen movie stars fall in love, do movies together, become award-winning and legendary actors, and live happily ever after. It's like straight out of a fan fiction story. 

The pair met in 1997 at Reese's 21st birthday party, where she told him, "I think you're my birthday present," and naturally, he loved it. He actually loved it so much that they got engaged the following year! By March 1999, they were starring in Cruel Intentions together, and they were married in June. They had two children, and three years after having their second baby, they announced they were divorcing in October 2006.

8. 50 Cent and Chelsea Handler

Special shout out to my favorite ex @50cent (and the only ex-boyfriend I am still asked about in every interview) who gets an extra special shout out in my @hbomax special. Now, everyone will know that you’re one big fat teddybear. Xx pic.twitter.com/j20l7XUhgE

— Chelsea Handler (@chelseahandler) August 21, 2020

@chelseahandler / Via Twitter: @chelseahandler

The fever dreams I mentioned earlier — that's often what happens when I think back to this relationship. Back in 2010, the pair dated for two months after meeting on Chelsea's old talk show, Chelsea Lately. He bought her flowers, went to visit her in New Orleans, and they spent the weekend together. 

When the paparazzi pictures started floating around of them on a date in New Orleans, Chelsea took it upon herself to post some hilarious pictures of her laying in bed with 50 Cent and still claiming they weren't dating. Even though they only briefly and casually dated, Chelsea still speaks very fondly of him and even refers to him as "her favorite ex."  Just as recently as May of this year, they've shown support for one another.

9. Lenny Kravitz and Nicole Kidman

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Nothing makes me more upset than not being a teenager in the early '00s, because I missed stuff like THIS. It's one that you would never imagine, especially looking at who her husband was prior to dating rockstar Lenny Kravitz (Tom Cruise) and who she married after (Keith Urban). The thing that really blew my mind about this relationship is that the two were engaged to be married, and it was never even confirmed until 2017 when Nicole Kidman finally spilled the beans.

The pair reportedly met and started dating back in 2003, when Nicole was subletting his Manhattan apartment while hers was being renovated. Yes, in 2003, people didn't get confirmation about their engagement until 14 years later... iconic. However, sadly, they broke up in December 2003 after spending Thanksgiving together at his Miami home. As a Big Little Lies fan, it's now even wilder to watch Nicole on the show with her almost-stepdaughter Zoë Kravitz.

10. Brad Pitt and Robin Givens

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Heartthrob central. Back in the 1980s, Robin Givens and Brad Pitt met in an acting class together before either of them were the stars we know them as today. They eventually saw each other again when Brad was signed on for the sitcom Head of the Class, which Robin was already working on. The pair only briefly dated, and she went on to tell Hollywood Life in an exclusive that he was "such a wonderful person."

Robin eventually married boxer (and sadly, her abuser) Mike Tyson in 1988, and they divorced in 1989. Robin and Brad became closer after her separation from Mike. However, Tyson alleged in his 2013 memoir that he caught Brad and Robin in bed together before they separated. He also claimed that he pulled into her driveway on a separate occasion and caught them in the car together. On Watch What Happens Live with Andy Cohen in 2019, Robin said Tyson never caught her in bed with Brad. However, they were in the car together in her driveway after coming back from a screening.

11. Ariana Grande and Big Sean

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Although my allegiance will forever be to Big Sean and Jhené Aiko, this is just one of those things that will forever live in my brain and is consistently brought up every time I listen to old Ariana songs. The drama it carried was immense, and I'll never forget how wild social media was over it.

Naya Rivera (who Big Sean was engaged to before dating Ariana) claimed in her memoir, Sorry Not Sorry that after fighting with Sean for five days straight and him subsequently telling her he didn't want to see her, she used her key to his house to go check-in. When she got there, she said that she went downstairs and found Ariana there with him listening to music. She also said that she learned of their breakup and the end of their wedding plans in April 2014. At the same time, the rest of the world did. Big Sean was publicly with Ariana by August.

12. Lea Michele and Matthew Morrison

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The childhood Gleek in me is screaaminngg. I don't know if I've always known about this or if my brain needed to block it out of my memory for my own safety, but this is one that definitely gets me. Especially because any of my OG Gleeks will remember those first few seasons of the show when fans were ADAMANT that Matthew and Lea were in some sort of secret relationship.

Back before the Glee days, Lea and Matthew were both working on Broadway, and she revealed these details in her book Brunette Ambition: "I had worked on Broadway with Jenna Ushkowitz and Matthew Morrison before. Matt had been a friend of mine for years, and in fact, we'd actually dated back in the day for a Broadway beat." Oh, Ryan Murphy, the messy genius that you are.

13. Mariah Carey and Derek Jeter

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Yet another reason why I just know I was born in the wrong generation. Words can't even describe how elite it must have been to see a power couple like this. Two people who are some of the greatest at their crafts, and the universe brought them together. We just don't get stuff like this anymore, kids! Just from how fondly Mariah remembers this relationship, it makes me wish it really would have gone on forever! The pair dated from 1997 to 1998.

Mariah credits Derek and their relationship together as being the catalyst for her realizing she could no longer stay in her abusive relationship with music executive Tommy Mottola. She also mentions in her memoir, The Meaning of Mariah, that spending time with Derek's very healthy interracial family helped her come to terms with a lot of feelings she had about being biracial and coming from a "dysfunctional" family. 

14. Flavor Flav and Brigitte Nielsen

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You'll find NO complaints from me on this one. As someone who grew up with a millennial older sister, I can luckily recall myself glued to the screen to watch all of the mess on Y2K reality TV shows. Brigitte and Flav met on the set of the reality show The Surreal Life in 2004. From there, the pair immediately received a spin-off reality show that followed their relationship, titled Strange Love, in 2005.

Although they only dated for a year, the two of them, their relationship, and their shows indirectly gave us the greatness that is Flavor of Love, Rock of Love, I Love New York, etc. Just as recently as 2018, after Brigitte announced she was welcoming a child at 54, Flav went out of his way to send her endless love and support. "This pregnancy at over 50, it's amazing! It shows everybody in the world that everything and anything is possible. I was proud. I was siked to see her belly that big."

15. Azealia Banks and Jesse Bradford

@jessebradford / Via instagram.com

This pair only reportedly dated for a few months back in 2015, but that still doesn't stop it from popping up in my mind every once in awhile. Jesse Bradford (yes, cute little Cliff from Bring It On) dated the ever-controversial and outspoken rapper Azealia Banks. 

It all started when reports came out that the pair were seen together at Coachella in 2015, followed by being spotted at an afterparty that absolutely included them leaving together, and then came the series of overly couple-like Instagram posts from both Jesse and Azealia. It was a total whirlwind and pretty hush, as it was unclear why the pair stopped seeing each other.

16. Courteney Cox and David Arquette

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I really wanted them to make it. I know it's been over a decade and I have to move on, but it doesn't make it hurt any less. They barely even make movie-power couples like this anymore, especially HORROR MOVIE POWER COUPLES LIKE THIS. I feel like everyone's moved on, but I'm still here with Gale and Dewey.

David and Courteney met at a pre-party prior to filming the first Scream movie. David even said that for him, it was love at first sight. The pair fell in love during the filming of the first movie in the mid-90s, and they showed up hand in hand at the movie premiere in 1996. They got married in 1999 and welcomed their first child in 2004, all while giving us one of the best relationships on and off screen. By 2010, David was quoted saying that "relationships take a lot of work." After two years of trying to make it work, a separation, couples therapy, and still appearing in a huge franchise as lovers, the pair decided to file for divorce in 2012.

17. Dolph Lundgren and Grace Jones

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I mean, just look at them. How do you even follow up with any words after seeing this? Whoever created these two AND THEN MADE THEM DATE was completely out of hand. About a year and a half before the pair met in the early '80s, Dolph had a master's in chemical engineering and had just won a scholarship to the Massachusetts Institute of Technology in Boston.

He gave all that up when he met Grace in Australia while working as her bodyguard and realized MIT wasn't the path he wanted to take. Soon after, she was taking him to the infamous Studio 54 in New York City with Andy Warhol. Next thing he knew, he was trying out for a role in the James Bond movie, A View to a Kill (because Grace was already cast). However, he eventually ended up auditioning and getting the role of Ivan in Rocky IV. The pair dated for several years and provided us with paparazzi shots that were worthy of being in art collections.

Have a celebrity relationship that everyone's moved on from but you'll never forget? Let me know in the comments!