It’s time for a throwback, y’all, and it’s not even Thursday (unless you read this on a Thursday, and in that case—hey, happy Thursday).
You know about #Brangelina and Angie vs Jen. You know about Tom Cruise and Katie Holmes. But what about…Hilary Duff and Joel Madden? Cameron Diaz and Jared Leto?
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Yeah, I thought so. Dive in with me.
Mandy Moore and Wilmer Valderrama
Yup. The two dated when they were teenagers, at a mere 16 years-old. Mandy recently talked about Valderrama’s outlandish (and inaccurate) statement that he was her first.
However, despite the lie, the two are still friends.
Nicole Kidman and Lenny Kravitz
This one was a surprise to me, too, and I thought I knew every piece of weird celebrity gossip around.
The two were briefly engaged in 2002, after meeting when Kidman became Kravitz’s landlord. Crazy.
These days, Nicole spends more time hanging out with his daughter, Zoë, on the set of Big Little Lies.
Penelope Cruise and Tom Cruz
Maybe you knew about this, maybe you didn’t. Maybe I’m happy that we as a current society didn’t have to try and come up with a couple name for them.
They dated for 3 years, but broke up in 2004.
Ashley Olsen and Lance Armstrong
This one came as a legit surprise. Back in 2007, when Ashley was 21 and Lance was 36, the two briefly dated.
He is now with Anna Hansen, and Ashley dated another older man before getting together with her current boyfriend, Louis Eisner.
Fergie and Justin Timberlake
I mean, everyone remembers Justin Timberlake and Cameron Diaz, but does anyone remember Justin and Fergie?
They briefly dated back when N’Sync was still a thing, and even went to Hawaii together. But it was a casual thing.
Ryan Gosling and Sandra Bullock
Guys, there was a time when Ryan Gosling wasn’t with Eva Mendes (or, briefly, Rachael McAdams).
Ryan and Sandra co-starred in Murder by Numbers in 2002, and dated for about a year. They were 16 years apart.
Selena Gomez and Nick Jonas​
I feel like the Jonas Brothers dated, like, every popular singer in the 2000s? That’s what it feels like, anyway.
Regardless, the odd matchup of Selena and Nick occurred while she was on a break from dating Justin Bieber. It didn’t last long, but the two are definitely still friends.
Hilary Duff and Joel Madden
Long before he married Nicole Richie, Joel Madden kind of creepily dated Hilary Duff.
I say creepily, because she was 16…and he was 24. That right there is a big ‘ol yikes.
Kirsten Dunst and Jake Gyllenhaal
The extroverted Kirsten and the introverted Jake made quite the couple for a while. They met on the set of Spider-Man, and dated for two years before calling it quits.
Ryan Reynolds and Alanis Morissette
Believe it or not, these two were actually once engaged. The 2000s was a wild time, you guys.
Ryan and Alanis met in 2002, and eventually split in 2007. Alanis wound up writing her album, Flavors of Entanglement, about their breakup.
Matthew Morrison and Lea Michele
Yup, Mr. Schue and Rachel Berry dated once upon a time.
Before they were ever on Glee, Matthew Morrison and Lea Michelle ran in the same Broadway circles. They dated for a quick second before forming a more professional relationship.
Wilmer Valderrama and Lindsay Lohan
Wilmer and teen idols was definitely a thing. Unfortunately, Lindsay Lohan when they dated, which needs to stop being a thing in Hollywood and also life.
Lindsay made a guest appearance on That 70’s Show while they were dating.
Rihanna and Shia LaBeouf
Hey, the award for weirdest couple definitely goes to this duo.
They two went on one date in 2007, but neither felt anything for the other. He told Playboy that they’re still friends.
Matthew McConaughey and Janet Jackson
I…could never have imagined this pairing.
They met at the Grammys in 2002, which seems to be the magic year for weird couples. They only briefly dated before amicably parting ways.
Cameron Diaz and Alex Rodriguez
Before A-Rod popped the question to Jennifer Lopez, he briefly dated Cameron Diaz back in 2011.
Oh, how so much has changed since these days.
Kate Bosworth and Orlando Bloom
Kate and “Orly” were the couple in 2004. They were everywhere back in the day, as they were both at the height of their fame at the time.
They broke up after two years of dating in 2006.
Winona Ryder and Matt Damon
Say what? In 1997, Gwyneth Paltrow introduced super famous Winona to a young Matt Damon, and they immediately a spark was lit.
They broke up in January of 2000, but they remain on good terms.
Macaulay Culkin and Mila Kunis
Hm. Okay. This couple is probably as surprising as Macaulay Culkin’s current relationship, which is with Brenda Song. In case you didn’t know that was happening.
Anyway, he and Mila Kunis actually dated for eight years. They broke up in 2010.
Ben Affleck and Gwyneth Paltrow
Beneth? Bwyneth? Hm…doesn’t have a ring to it. Ben and…Gwyn dated from 1997 to 2000 before finally splitting.
They starred in the film Bounce together during that time, which has a 52% rating on Rotten Tomatoes. Ouch.
Vanessa Hudgens and Josh Hutcherson
Gabriella and Peeta, who would have thought?
Josh dropped the info that he and Vanessa Hudgens dated while promoting the movie they starred in together, Journey 2: The Mysterious Island. The romance was short-lived.
Evan Rachel Wood and Marilyn Manson
Before she was starring in Westworld Evan Rachel Wood was in a deeply odd relationship with Marilyn Manson.
She starred in his music video for “Heart-Shaped Glasses,” which is very NSFW.
He was once quoted as saying, “I have fantasies every day about smashing her skull in with a sledgehammer.” Thankfully, they’re not together anymore.
Kim Kardashian and Nick Cannon
I guess Kanye West and Mariah Carey are one degree away from each other.
Kim Kardashian dated Nick Cannon for a whopping four months in 2007. According to Nick, they broke up because Kim lied about her sex tape. Uh…okay!
Michelle Rodriguez and Cara Delevingne
I’m already sad that this didn’t work out, and I only just found out about it.
In 2014, Cara Delevingne and Michelle Rodriguez dated for six months. They vacationed in Cancun, went to basketball games, and even played with tigers together before calling it quits.
Nick Lachey and Kim Kardashian
Kim sure dated some Nicks before settling down with Kanye, huh?
After he divorced Jessica Simpson in 2006, Nick Lachey dated Kim Kardashian for a whole week! He claims that she used him to get famous, which is ridiculous.
Isn’t that Kris’ job?
