Ah, the 2000s. A time when Friends was still on the air, the Harry Potter films were in full swing, and punk rock was at an all-time high.
Another beautiful thing about the ’00s was the bizarre celebrity relationships. The ones we look back on and think, huh??
Sure, they might have made sense at the time, but for those celebs who have moved on to find their one true love, we can’t help but question their past flings.
I totally forgot some of these couples dated!
The 2000s were truly a time for one-year marriages to people you weren’t completely sure about, and fashion choices you were sure to regret. Amirite superstars?!
1. Matthew McConaughey and Janet Jackson.
These two love birds had a short lived romance after they met at the 2002 Grammy’s show, as pictured above, and hit it off.
I feel like in their short time together they must’ve compared abs at least once.
2. Ashley Olsen and Lance Armstrong dated back in 2007, despite having a 15-year age gap.
They attempted to keep their romance on the down low, and according to E! Entertainment , his friends allegedly warned him that their age gap might be problematic for his image.
3. Hilary Duff and Joel Madden dated from 2004-2006.
They started dating when Hilary was only 16, and Joel was 24.
Obviously hearing that now casts a shadow on what we nostalgic people might view as one of the most iconic teen couples of our fleeting youth.
In an interview with Cosmopolitan magazine, HDuff recalls that time in her life.
When asked about the relationship , she said, “I had a 26-year-old boyfriend, so everyone can make their own assumptions about what I was doing.”
4. Tom Cruise and Sofia Vergara were an (almost) item back in 2005.
They nearly had a fling after his split from Penelope Cruz, who left him after he encouraged her to embrace Scientology and pushed her to take classes. According to Business Insider, heir mutual friend Will Smith set them up!
5. Taylor Swift and John Mayer were involved from 2009-2010. John inspired Taylor’s heartbreaking ballad “Dear John.”
They’ve gone through some wild times, but recently he put their differences aside to compliment her newest album “Reputation,” calling it a “fine piece of work.”
6. Drew Barrymore and Tom Green were married from July to December in 2001.
Green reflected on his time with Drew during an interview with Oprah, “I don’t really tend to talk about it that much comfortably [or] publicly. All of that was part of that sort of crazy, whirlwind of a time.”
7. Wilmer Valderrama and Lindsay Lohan dated back in 2004.
Lohan even made an appearance on That ’70s Show , which Wilmer starred in. Their relationship was quite the scandal since she was underage at the time.
8. Ryan Gosling and Sandra Bullock dated from 2002-2003. Ryan was 21, Sandra was 37.
To be fair, Sandy B is a hot momma and somehow looks even better now than she did back then. Ryan was lucky to have her!
9. Evan Rachel Wood and Marilyn Manson began dating in 2007.
This controversial couple captivated the minds of fans everywhere. Evan was just 18 when they met, and began dating soon after.
Manson caused a stir when he said he had fantasized about killing Evan. He told SPIN, “I have fantasies every day about smashing her skull in with a sledgehammer.”
The pair got engaged but called it quits in 2010.
He said some other super alarming things in his interview — about how poorly he took their break-up, and the wild things he did to show her his pain.
10. From 2001 to 2003, Matt Damon and Winona Ryder gave us major relationship goals.
Winona was a teen queen and Matt was on the rise, so it was only a matter of time before their mutual friend Gwyneth Paltrow introduced them.
11. Before Kim Kardashian was one half of Kimye, she dated Nick Lachey!
Post-Ray J and Pre-Kanye, Kim got into this 98-degrees alumnus flirtationship for a brief fling.
Obviously, Kim grew out of it, but they honestly made a good couple. Does he look like her lawyer? Or massage therapist? Kind of — but they still cute!
12. Edward Norton and Salma Hayek dated for four years.
Um, exsqueeze me? This union has shocked me to the core. Yes, Edward Norton is an ’90s icon, and so is Salma. But this is just so unexpected.
The two started dating after his breakup with Courtney Love.
When Courtney was interviewed about her relationship with Edward, they seemed to repeatedly ask why she didn’t marry him at the time.
She responded that she wasn’t ready to, didn’t want to, and didn’t know how to.
13. Ryan Reynolds and Alanis Morissette were an item from 2002 until 2007 when they mutually ended their engagement.
No offense, but name a more iconic, timely, and insanely good looking brunette couple! They’re also both Canadian, so there’s that, I guess.
14. Ashton Kutcher and Brittany Murphy dated back in 2002. They were co-stars in Just Married.
Their relationship made everyone watching them believe in love — on-screen and off.
15. Rihanna and Shia LaBeouf remain friends after a failed first date back in 2007.
In an interview with Playboy magazine, he said “It never got beyond one date. The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”
Oooh! Do you think Rihanna wrote any songs about Shia?!
Probably not, TBH.
Rihanna is too busy being one of the most successful women on the planet for her music and businesses that she probably isn’t thinking about men!
16. Jared Leto and Cameron Diaz were an item in 1999 and got engaged a year later. Unfortunately, they called off the engagement in 2003.
Seeing our girl Cameron — an angel in real life and in Charlie’s — date a bad boy like Jared was an out of body experience. What is you doing, boo boo?
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17. It’s hard to believe, but Kim also dated Nick Cannon!
But honestly, considering how beautiful and dope Kim is, it’s not surprising that a few famous men have tried their hand at securing her as wifey.
18. Anne Hathaway and Topher Grace were an item back in the day! They dated from 1999-2001.
They’re cute!
As a side note though, isn’t it crazy how Topher Grace is in so many movies that we’ve seen, but we’re just now seeing his name for the first time (probably)? Hmmst.
Which couple was your favorite? COMMENT and let us know!
I’m gonna have to go with Matthew McConaughey and Janet — that ‘ish is WILD and ICONIC!
