The 2000s were definitely a pinnacle of celebrity couples. Many will always be memorable, such as Britney Spears and Justin Timberlake — those denim outfits belong in a museum — but other, less photogenic ones seem to have escaped to the back corners of the Internet's mind.
Whether the celebs were simply making out, had a brief fling, or were in a full-on relationship, these 17 couples's romantic histories deserve to be remembered for posterity.
These two actually went out on a date in 2007, but it reportedly didn't end very well. LaBeouf told Playboy, "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."
They famously dated from 2006 to 2007, with Mayer describing Simpson as "crack cocaine." In a tell-all interview with Playboy, Mayer said their relationship was like "sexual napalm." They were also parodied on Saturday Night Live, which is the easiest way to tell if your relationship is weird to others or not.
How does a persnickety British music judge end up dating a former Baywatch star? Well, according to Electra, it never happened, not in the ~true~ dating sense. After being flirty texters, Electra apparently made out with Cowell at his party, which is how the paparazzi "uncovered" their relationship. Still, Electra maintains: "We never dated. We didn’t date ... He wasn’t my man." But since they did kiss (probably), we're keeping them on this list.
The two briefly dated in 2001, and Moby told Spin that his relationship with Portman made him "the target of a lot of nerd wrath," which makes sense, actually.
The two started dating in 2006 — when she was 19 and he was 36. They were engaged in 2010, but eventually broke up. "I just don’t think we were right for each other," Wood said of Manson in 2015.
These two reportedly started dating in 2009, and MTV News made a handy timeline of their flirtation. After much speculation about whether they did or did not date, Handler set the record straight: "We dated, very casually."
These two reportedly had a brief fling in 2002 after meeting at the Grammys. While McConaughey claimed they were "just friends," Jackson did admit to their romance.
The couple dated back in 2007, despite their 15-year age difference. According to the book Cycle of Lies: The Fall of Lance Armstrong, the athlete's friends were not on board with his relationship, fearing it would destroy his image.
Yep, Christian Grey and Anna Karenina dated from 2003 to 2005. Apparently, Knightley is the one who helped Dornan's acting career, introducing him to her agent. When they broke up, he apparently even wrote a song about his feelings.
This odd couple briefly dated in 2006, and Lachey later claimed that Kardashian only used him to get herself famous.
The two didn't officially date, but they were reportedly spotted making out at the Sundance Film Festival in 2008. According to an unnamed source from Page Six, "This is not the first time they have made out — there just weren’t any cameras around before. She likes him and she thinks he is really sexy and fun."
Duff and Madden dated from 2004 to 2006; when they first got together, she was 16 and he was 25. The details of their romance are a bit, um, controversial, as Duff told Cosmopolitan: "I had a 26-year-old boyfriend. So everyone can make their own assumptions about what I was doing."
The two were seen making out after a screening of Farrell's film The Recruit, but Farrell set the record straight when he said, "We're just mates, and we're not dating."
These two had a low-key relationship for eight years, beginning in 2002. According to Page Six, "The split was amicable, and they remain close friends."
Before Gosling dated his The Notebook costar, Rachel McAdams, he was with Bullock. They started dating after working on their film Murder by Numbers and were together from 2002 to 2003. Gosling spoke about Bullock and McAdams to The Times, saying, "I had two of the greatest girlfriend of all time. I haven’t met anybody who could top them."
According to a New York Post article — which has since been deleted — Cruise allegedly asked Scientology leaders to set him up with someone from his list of women he'd like to date. Business Insider summarized the article, which explained how Cruise wooed Vergara with flowers and chocolate at Will Smith's pre-Oscar party. Later on, Cruise's pal (and Scientology leader) David Miscavige apparently tried to prep Vergara to be Cruise's wife, which would mean renouncing her Catholic faith and adopting Scientology in its place. The whole ordeal sounds super sketchy, TBH.