No one is exempt from those romantic flings we wish we could forget, but when it comes to these former celebrity couples, we did!
We all remember that Owen Wilson and Kate Hudson were on-off Hollywood sweethearts, but did you know that the "Zoolander" actor and Sheryl Crow were a thing from 1999 to 2001? How about Johnny Depp and Ellen Barkin or Lance Armstrong and Ashley Olsen? All of these somewhat odd couples managed to find each other, crossing age barriers and genres of fame in the process.
Check out these celebrities who will surely make you say, "They dated?!"
Owen Wilson, Sheryl Crow
The couple broke up in 2002, but there were no hard feelings. "I love Owen. He's so talented, and a great, great person," Crow said about the actor the same year.
In 2007, then 21-year-old Olsen was spotted making out with Armstrong, 15 years her senior, at Rose Bar in New York. Yeah, we don't really get it either.
Ryan Gosling, Sandra Bullock
The hunky heartthrob and funny girl were together from 2002 to 2003. "I had two of the greatest girlfriends of all time. I haven't met anybody who could top them," Gosling told Us Weeklyin 2011 (about Bullock and Rachel McAdams, whom he dated afterward). We wonder what current amour Eva Mendes might have to say about that?
Roger Ebert, Oprah Winfrey
Roger Ebert and Oprah went on two dates way back when the two were just starting out in Chicago -- and Ebert counts himself as her mentor. "Yes, it is true, I persuaded Oprah to become the most successful and famous woman in the world," Ebert wrote in 2005.
Andre Agassi, Brooke Shields
Nowadays, it's hard to imagine that one of the most high-profile couples in the '90s was tennis star Andre Agassi and actress Brooke Shields. The couple dated for six years before marrying in 1999; they divorced just two years later.
George Clooney, Talia Balsam
George Clooney may be the ultimate bachelor, but he did get married, just once, to actress Talia Balsam. (Balsam is now married to John Slattery of "Mad Men").
"I was married, so I gave it a shot," Clooney told Piers Morgan in 2011. "I've proven how good I was at it, and I just...I'm allowed one."
Winona Ryder, Jimmy Fallon
Winona Ryder and Jimmy Fallon were reportedly linked in 2002, though she denied a relationship in W magazine that same year: "I do date once in a while, and I've gone out with wonderful people in the past. Although not with Jimmy Fallon, who everyone thinks is my boyfriend. We're just great friends."
Helen Hunt and Matthew Broderick gave love a shot in 1987 and although happily every after wasn't in the cards for the pair, the couple did forge a lifelong friendship. Hunt and Broderick are even comfortable enough with their relationship that they filmed a sex scene together for 2008's "Then She Found Me."
Conan O'Brien, Lisa Kudrow
These two funny people dated when he was a writer for "Saturday Night Live" and she was working as a comedian in Los Angeles. "He was really smart, really funny and he thought I was funny, but found we were better as friends," Kudrow said of their brief romance.
Sarah Jessica Parker, Robert Downey Jr.
By his own admission, Robert Downey Jr. was less than a model boyfriend to Sarah Jessica Parker, whom he dated from 1984 to 1991. "I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica, because it is the furthest thing from what she is," Downey Jr. said of their relationship.
Drew Barrymore, David Arquette
These two Hollywood staples were briefly linked in 1991 -- eight years before they starred together in 1999's "Never Been Kissed."
Carson Daly, Tara Reid; Katie Holmes, Chris Klein
Cutest -- and weirdest -- double date ever? Carson Daly/Tara Reid and Katie Holmes/Chris Klein are the epitome of the '90s here.
Moby, Natalie Portman
According to Moby, his fling with Portman caused a lot of nerd wrath. "You don't date Luke Skywalker's mom and not have them hate your guts," he said about their romance.
The telegenic "There's Something About Mary" co-stars dated for three years before splitting in 1998 -- the same year the hit comedy hit the big screen.
The romance between the Smashing Pumpkins frontman and the reality star came out of nowhere, and left just as quickly as it arrived.
Shia LaBeouf, Hilary Duff
LaBeouf and Duff, who just gave birth to her first child, went on an epically bad date -- according to LaBeouf himself. "Probably the worst date either of us have ever had," the "Transformers" star told Details of their failed connection.
Emma Stone, Kieran Culkin
After meeting on the set of 2009's "Paper Man," Stone and Culkin were rumored to be dating. Stone is now currently dating "The Amazing Spider-Man" co-star Andrew Garfield.
You better believe it: In 1992, Danson was apparently so smitten with Goldberg during the filming of "Made in America" that it led to a divorce with his then wife-of-16-years, Casey, the next year. "I'd walk in Whoopi's shadow for the rest of my life--I adore the woman," Danson said about Goldberg.
Sean Lennon, Leelee Sobieski
John Lennon's son and Sobieski were spotted canoodling during a Rock & Roll Hall Of Fame induction in 2004, when the former teen star was just 20 years old.
Jake Gyllenhaal, Natalie Portman
These teen stars were linked twice: first, in 2006 (pictured, strolling in New York); and in 2008, shortly before co-starring in "Brothers." Gyllenhaal and Portman remain pals -- the latter offered a friendly roast of Portman in January 2011, when he said: "She is elegant, graceful, has amazing eyebrows... is talented, really short, funny, smart, dedicated, incredibly kind."
Ryan Reynolds, Kristen Johnson
Before Blake, before Scarlett, before Alanis, Reynolds dated yet another famous face: Kristen Johnston, of "Third Rock from the Sun" fame (pictured together here, in 1999).
Matthew Morrison, Kristen Bell
Bell and Morrison both attended New York University, where they "dated very briefly." Also, Bell calls the "Glee" star "Matty." Everybody say awww.
Edward Norton, Courtney Love
This unlikely couple dated for three years in the '90s after co-starring in "The People vs. Larry Flynt" together, and they were even rumored to be engaged. Years later, in 2010, Love would blast Norton on Twitter over an alleged $300,000 she said the actor owed her.
Minka Kelly, Donald Faison
Before she got together with Yankees star Derek Jeter, Kelly dated the "Clueless" actor for a year, from 2004-2005.
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