Admit it: By now, it seems like everyone in Hollywood has hooked up with one another at one point or another. Sure, there are power couples like Blake Lively and Ryan Reynolds or Mila Kunis and Ashton Kutcher, but those are more recent. However, if you go back a couple of years before then you’ll see that there used to be other people in the picture.
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In this day and age, it’s hard to forget about stuff when everything is pretty much preserved on the internet and you can always look it up. Let’s take a trip down memory lane and have a look at 29 celebrity hookups that happened once upon a time.
Colin Farrell & Britney Spears
2003 was a truly magical time of quirky outfits and funky hairstyles. In 2003, things seemed unreal. Joe Millionaire was a reality TV show that was fun to watch. In that same year, Freaky Friday came out.
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Meanwhile, on the more real side of Hollywood, Britney Spears was hooking up with known bad boy Colin Farrell. They walked up to the red carpet and made out everywhere. Bless these innocent lovers and bless that magical time.
Tupac & Madonna
This seems unbelievable, right? Like, did this actually happen? Well, believe it cause it really did. Madonna opened up that she had a brief fling with Tupac in the early 90s— just before he passed away in 1996.
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This claim was further supported in an unauthorized Madonna biography, too. If you still don’t believe the hookup happened, just know that even Tupac’s brother said his brother and Madonna actually hooked up.
Mariah Carey & Derek Jeter
If you don’t remember who Derek Jeter is, he is an American former professional baseball shortstop. Around 1997 or 1998, Mariah Carey and Derek Jeter had a brief hookup. Look at them! They look so good together.
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The pair even went to spring training. But sadly, the public eye can be cruel. It’s hard to be a couple when one is one of the world’s best singers and the other one is one of the world’s best athletes without being under public scrutiny. Sadly, it just wasn’t meant to be.
Brad Pitt & Christina Applegate
Christina Applegate and Brad Pitt began dating in 1989. Applegate was only 17 and Pitt was only 25 when the relationship began. At that time, they were still trying to figure out how to make a name for themselves in Hollywood.
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Sadly, the relationship didn’t last long. The relationship ended when Christina Applegate ditched him for someone else during the night of the 1989 VMAs. Who would’ve thought that she would actually ditch THE Brad Pitt?
Mila Kunis & Macaulay Culkin
Although Mila Kunis and Ashton Kutcher seem like the ultimate dream couple, that wasn’t always the case. She and Home Alone star Macaulay Culkin actually were in a relationship from 2002 until 2011.
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The two were actually quite serious and kept their relationship private, which is probably why not a lot of people knew about it. Sadly, Mila often found it hard while dating Macaulay because of how his fans reacted to the relationship and how little privacy they had.
Gwyneth Paltrow & Ben Affleck
Everyone probably remembers that time Gwyneth Paltrow dated famous hottie Brad Pitt, but did you know that she also had a thing with Ben Affleck? The pair were rumoured to have an on-again, off-again fling from 1997 to 2000.
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In 2015, Paltrow opened up to Howard Stern, “He was not in a good place in his life to have a girlfriend.” After the two finally broke up, Affleck dated JLo and Paltrow married Coldplay frontman, Chris Martin.
Justin Timberlake & Fergie
When you think of who Justin Timberlake’s ex-lovers were, the people that would most likely come to mind would be Britney Spears or Cameron Diaz. However, did you know that he also dated Black Eyed Peas member Fergie?
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That’s right! Justin and Fergie were casual lovers for a while. Fergie opened up to Cosmo, “Justin and I would go out together and have fun and make out. We went to Hawaii together, but we were never serious. He was Mr Right Now.”
Whitney Houston & Ray J
If you ever think we’re living in a simulation, just remember this: we live in a world where Ray J and Whitney Houston were casual lovers. Even though they had a 17-year age gap, they were seen out in public often.
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They remained on and off until Whitney’s death. A few days before Whitney’s death, the pair were seen having dinner in a Los Angeles restaurant. Ray J was crushed upon learning about Whitney’s death.
Kylie Jenner & Cody Simpson
There are couples that really surprise us. Kylie Jenner and Cody Simpson are one of them. Before Kylie dated Tyga and Cody dated supermodel Gigi Hadid, these two were rumoured to have been romantically linked.
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The pair sparked dating rumours in 2011 when they were photographed on a bunch of dates, but it wasn’t until years later that it was confirmed. Cody admitted that he had trouble adjusting to the paparazzi surrounding them.
Halle Berry & Danny Wood
Think of it like this: The year is 1990. The century was coming to an end soon, and New Kids On The Block was everyone’s favourite boy band. The gorgeous hottie Halle Berry was getting romantic with NKOTB’s Danny Wood.
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Sadly, the couple didn’t last, but Danny likes to remind us that he once was hooking up with one of the hottest chicks in Hollywood. During Watch What Happens Live with Andy Cohen, when asked who his most famous hookup was, he said, “Everyone kinda knows this, but I dated Halle Berry back in the day.”
Kim Kardashian West & Nick Lachey
You might think you’re in the loop with all the people the Kardashian/Jenner sisters have dated but think again. Before Kim Kardashian was actually famous, she was dating 98 Degrees member Nick Lachey.
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Unfortunately, it was nothing but a short-lived romance. Lachey doesn’t think of her as an ex, saying the calling her an ex would be “a little bit of a liberal use of the term.” He also claims Kim used him to get famous.
Megan Fox & David Gallagher
I’m sorry but how did we miss Megan Fox’s steamy whirlwind romance with 7th Heaven star David Gallagher?! The two dated from 2003 to 2004, when she was just at the beginning of her acting career.
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Later that year, they called it quits. Fox then had an on-and-off relationship with Brian Austin Green and didn’t become permanent until they got married in June of 2010. Then, the couple split and, now, Fox is dating Machine Gun Kelly.
Kate Hudson & Alex Rodriguez
Remember when American professional baseball player Alex Rodriguez called it quits with his wife Cynthia Scurtis in 2008? First, rumours circulated that he was getting cosy with Madonna (who claimed they were just friends).
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Then, the next thing we know, he and Kate Hudson started dating circa 2009. She even attended his baseball games together with Goldie Hawn and Kurt Russell. The pair ended their romantic relationship around December 2009.
Cameron Diaz & Alex Rodriguez
After Kate Hudson and Alex Rodriguez ended things, he began dating Cameron Diaz. You may have forgotten all about it because nobody really saw it coming. But it did. It really did. She even fed him popcorn in public.
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Alex Rodriguez has an impressive history of dating beautiful blondes. In 2011, Alex reportedly broke up with Cameron. This happened just one month after the actress finally spoke up about their relationship in public.
Emma Stone & Kieran Culkin
This was also a pairing we honestly found quite hard to believe, but it actually happened. We find it unbelievable, not because they seem like different people, but simply because we just never saw this coming.
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In case you don’t know who he is, Kieran Culkin is Macaulay Culkin’s younger brother. In 2009, the two were briefly in a relationship. They kept their relationship really private, but sadly, some relationships just don’t work.
Ryan Reynolds & Scarlett Johansson
Although we are completely in love with Ryan Reynolds and Blake Lively’s relationship, Reynolds was actually married to Scarlett Johansson first. They were married for 3 years before they split up in 2011.
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Scarlet says, “I mean, the first time I got married I was 23 years old. I didn’t really have an understanding of marriage.” Luckily, it seems like both people are happy with their partners now. Ryan is married to Blake, while Scarlet is married to SNL star Colin Jost.
Hilary Duff & Frankie Muniz
We thank Agent Cody Banks for giving us this cute couple. Hilary and her movie co-star Frankie Muniz started dating in 2002. They were a couple for about 2 years before they ended things in 2004.
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Thankfully, there are no hard feelings. In 2016, Frankie tweeted a pic of Hilary and him on a motorcycle with the caption, “This car took me on my first date, picking up @HilaryDuff. I’m assuming it looked something like this photo! Yes!!”
Jennifer Love Hewitt & John Mayer
Let’s be honest here: We could do an entire story just talking about all the girls John Mayer has dated, but we’re not going to do that. It’s 2021 and people are free to date whoever they want as long as it’s consensual.
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However, there are some women John Mayer dated that you probably don’t remember. One of these women is Jennifer Love Hewitt. In 2002, the pair were a couple. The song Your Body Is A Wonderland is even dedicated to her.
Hilary Duff and Aaron Carter
This is another relationship where we like looking back on with some fondness. Hilary Duff and Aaron Carter met on the set of Lizzie McGuire after he guest-starred for an episode on the show. He was actually still 13 when they started dating.
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Then, things just started going sideways. Carter admits he got “a little bored” and just started getting to know Lindsay Lohan. He got back together with Hilary, but sadly, he ended up cheating on her with her best friend. Yikes.
Penelope Cruz & Tom Cruise
I’m going to spare you some dad puns on their family names and instead remind you that the two met on the set of Vanilla Sky and fell in love. They were together from 2001 until 2004 and parted ways in January of that year.
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Cruise’s publicist assured people that the split was “amicable,” and Cruz’s rep also said, “They remain good friends and still talk often,” noting, “There is no other person involved.” They also said, “The relationship just ran its course and they decided not to be girlfriend and boyfriend anymore.”
Ryan Reynolds & Melissa Joan Hart
Okay, you may be complaining that you’re seeing another Ryan Reynold slide, but just hear us out. Let’s go back to the days of Sabrina the Teenage Witch when Ryan reportedly hooked up with Melissa Joan Hart.
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Ryan was still 17 at that time and Melissa 19. Melissa reveals in her 2016 memoir that Blake actually knows about their brief romance. In fact, she actually reached out to Melissa to “help her with a birthday present for Ryan.” What could it have been?
Mandy Moore & Wilmer Valderrama
Before Wilmer Valderrama became more known as Demi Lovato’s ex, Lindsay Lohan’s ex, or Minka Kelly’s ex, he was first Mandy Moore’s ex. The pair had a relationship back in 2001 and broke up in 2002.
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Sadly, it seems like things were kinda messy for the couple. Wilmer told Howard Stern that he took Mandy’s virginity while they were together, but Mandy called him out for lying. In an interview with Elle, she said his comment was “utterly tacky, not even true, and it hurt my feelings because I like him.”
Hayden Panettiere & Jesse McCartney
Rumours sparked that Jesse McCartney, then 21, and Hayden Panettiere, then 19, were dating when they were spotted making out rather steamily. Rumours also circulated that Hayden and then-boyfriend Milo Ventimiglia, then 31, had broken up.
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Reports say Hayden was seen “sitting on Jesse’s lap while he kissed her neck. Then, she got up and did some crazy sexy dance in his lap.” Then, the two “went outside to smoke and he wrapped his arms around her from behind and was kissing her neck again.”
Minka Kelly & Donald Faison
Honestly, we’re not sure how this happened. Was Donald Faison sweet, charming, and funny? How and where did they meet? We’re dying to know! Anyway, this happened in 2005, following Donald’s divorce from his ex-wife Lisa Askey.
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The couple lasted just short of two years before they called it quits. After that, Minka dated musician, John Mayer. Donald, on the other hand, is now married to CaCee Cobb, who is Jessica Simpson’s BFF.
Will Smith & Tyra Banks
Like most beginnings of a Hollywood romance, the two met on the set of The Fresh Prince of Bel-Air where Tyra made her acting debut. The couple were together for a year before they ended their brief romance.
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At that time, Will was only 24 and Tyra was around 19. After the relationship ended, they went their separate ways but have remained friends since. As for their romantic lives, well you know what happens after.
Zoë Kravitz & Ben Foster
Zoë just keeps on setting the bar high and making us drool. Cast as the new Catwoman in the upcoming Batman film, she’s officially everyone’s dream girlfriend. But did you know that she was once the real-life girlfriend of Ben Foster?
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He was 27 and she was still 19 when they became romantically involved. He was one of her first public relationships. The pair didn’t last for an entire year, though, but they do look cute together, don’t you think?
Ashton Kutcher & January Jones
Before Ashton Kutcher dated Mila Kunis or Demi Moore, he was in love with January Jones. They dated for three years—from 1998 to 2001. Although they were in love for a while, it seems like the relationship didn’t really end on good terms.
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January revealed to GQ in 2009, “[He] was not supportive of my acting. He was like, ‘I don’t think you’re going to be good at this.'” She added: “So— f— you!” We don’t know what actually happened behind closed door, but, alas, life just happens.
Vanessa Hudgens & Josh Hutcherson
Although Vanessa is most known for being Zac Efron’s ex girlfriend, she also had a brief fling with Hunger Games Josh Hutcherson. The two met on the set of Journey 2: The Mysterious Island where they both played leading roles.
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The couple briefly dated, although we never really know for how long. When they did promo for the movie, they were asked by interviewers how long they’ve been dating. They had to awkwardly tell people that they weren’t dating anymore. On the bright side, they do seem to still be good friends.
Selena Gomez & Taylor Lautner
This is another pairing we never really expected to happen. The two met in Vancouver when Selena was shooting her movie Ramona and Beezus while Lautner was filming Twilight: New Moon.
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Because they both had big names, they were constantly surrounded by paparazzi wherever they went. Things may not have worked out between them, but Selena said, “He is so sweet. Taylor has made me happy. I didn’t know I could be that happy.”
