Whoopi Goldberg, Ted Danson
You better believe it: In 1992, <a href="http://www.people.com/people/archive/article/0,,20110576,00.html" target="_hplink">Danson was apparently so smitten with Goldberg</a> 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<a href="http://www.popeater.com/2011/01/10/jake-gyllenhaal-roasts-natalie-portman/" target="_hplink"> latter offered a friendly roast</a> of Portman in January 2011, when he said: "She is elegant, graceful, has amazing eyebrows ... is talented, really short, funny, smart, dedicated, incredibly kind."
John Tesh, Oprah Winfrey
What's even more bizarre than Oprah and Roger Ebert? Oprah and musician/television host John Tesh. Tesh allegedly left Oprah broken-hearted in the 1970s when <a href="http://articles.nydailynews.com/2010-04-11/gossip/27061375_1_john-tesh-connie-sellecca-kitty-kelley" target="_hplink">he bolted in the middle of the night </a>from the apartment they shared in Nashville, Tenn.
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<a href="http://www.usmagazine.com/celebrity-body/news/kristen-bell-reveals-she-once-dated-glees-matt-morrison-2010239" target="_hplink"> "dated very briefly." </a>Also, Bell calls the "Glee" star "Matty." Everybody say<em> awww.</em>
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 was even rumored to be engaged. Years later, in 2010, <a href="http://www.huffingtonpost.com/2010/02/26/courtney-love-attacks-edw_n_478073.html" target="_hplink">Love would blast Norton on Twitter </a>over an alleged $300,000 she says 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.
Brad Pitt, Robin Givens
A pre-fame Brad Pitt dated Givens in 1989, in the midst of a nasty breakup with ex-husband Mike Tyson. "As I go to my car she drives up with the handsome Brad Pitt," <a href="http://www.dailymail.co.uk/tvshowbiz/article-2125932/Mike-Tyson-admits-seeing-ex-wife-Robin-Givens-Brad-Pitt-turned-wet-noodle.html#ixzz1xo06DpM1" target="_hplink">Tyson recalled</a> in April 2012 on "Conan O'Brien." "It just totally overwhelmed me ... I had no energy to fight."
Christina Applegate, Brad Pitt
The Brad strikes again: This time, with the "Married with Children" actress in 1988.
Al Pacino, Diane Keaton
Keaton dated her "Godfather" co-star Al Pacino in the '80s; the relationship dissolved after Keaton pushed a marriage ultimatum on Pacino. She told <em>People</em>: "He's charming, hilarious, a nonstop talker. There was an aspect of him that was like a lost orphan, like this kind of crazy idiot savant. And oh, gorgeous! I was mad for him. I worked hard on that one."
Jennifer Lopez, Ben Affleck
Remember <a href="http://www.people.com/people/article/0,,627566,00.html" target="_hplink">Bennifer</a>? Ben Affleck was with another Jennifer before now-wife Jennifer Garner; the couple dated for 18 months and even got engaged, but split in 2004.
Meg Ryan, Russell Crowe
Hollywood's sweetheart and the Australian heartthrob enjoyed a jet-setting romance from 1999-2001, to much controversy: Ryan was still married to actor Dennis Quaid when the future lovebirds met on set of "Proof of Life. "Dennis was not faithful to me for a very long time, and that was very painful," <a href="http://www.theage.com.au/lifestyle/celebrity/meg-ryan-admits-to-breaking-russell-crowes-heart-20090403-9qzr.html" target="_hplink">Ryan told<em> InStyle</em></a>. "I found out more about that after I was divorced ... Russell didn't break up the marriage."
Seal, Tyra Banks
Seal sure has a thing for telegenic supermodels! Seal and Tyra confirmed their budding romance when they stepped out to the Essence Awards in 1996, but broke up shortly thereafter.
Aaron Carter, Lindsay Lohan
It's crazy to think about now, but Lohan and Carter were once a hot item, albeit not without some controversy. Carter had previously been dating that <em>other</em> teen star Hilary Duff, and <a href="http://newsroom.mtv.com/2011/08/15/love-triangle-hilary-duff-pregnant-aaron-carter-lindsay-lohan/" target="_hplink">cheated on her with LiLo.</a>
Dolph Lundgren, Grace Jones
The real-life "Bodyguard" romance between the Swedish chemical-engineer-turned-beefcake and Jones happened when she hired him as her bodyguard in Sydney. Lundgren then followed her to New York, where the two partied with Andy Warhol and the Studio 54 glitterati. "She was a very sweet lady, a handful on all levels but I wouldn't have done without her. I have the scars to prove it," <a href="http://www.guardian.co.uk/culture/2010/aug/21/one-last-thing-dolph-lundgren" target="_hplink">Lundgren said about Jones in 2010</a>.
Kelly Preston, Charlie Sheen
Not only did Sheen's relationship with then-fianc?e Preston end tumultuously, it ended with a bang -- when <a href="http://www.eonline.com/news/did_charlie_sheen_really_shoot_kelly/239915" target="_hplink">Preston was accidentally shot with Sheen's gun</a>, in 1990. "There's a beautiful person in there. He really is a great man," Preston would say about her former boyfriend nearly two decades later.
Josh Hutcherson, Vanessa Hudgens
Ah, live television. The "Hunger Games" star and Hudgens shared an <a href="http://www.huffingtonpost.com/2012/01/18/josh-hutcherson-and-vanes_n_1212160.html" target="_hplink">awkward moment on an Australian morning show </a>when an interviewer asked the pair how long they had been going out. "We're not," Hutcherson said. "We were at one point, but she broke my heart. No, I'm just kidding. That was a while ago. We're really good friends now."
Richie Sambora, Cher
Cher was involved with the Bon Jovi guitarist for two years in the early '90s. We bet the glamour-hair contests were awesome.
Enrique Iglesias, Sofia Vergara
It's strange to think of now, but Vergara was once more commonly referred to as <a href="http://www.people.com/people/archive/article/0,,20139975,00.html" target="_hplink">Iglesias' ex </a>before hitting it big with the ABC sitcom "Modern Family."
Drew Barrymore, Tom Green
In 2001, the Canadian comedian <a href="http://articles.cnn.com/2001-12-17/entertainment/green.divorce_1_divorce-irreconcilable-differences-ann-gurrola?_s=PM:SHOWBIZ" target="_hplink">filed for divorce</a> less than six months after marrying the then 26-year-old Barrymore, saying: "Drew is a wonderful woman, I love her very much. I wish our marriage could have worked out, I wish her much happiness."
Ashton Kutcher, January Jones
Before she was Betty on "Mad Men," Jones was a model for Abercrombie & Fitch, and a massively unhappy one at that. Then beau Kutcher didn't help much either -- or did he? "[He] was not supportive of my acting," <a href="http://www.gq.com/women/photos/200911/january_jones_mad_men_cover_story" target="_hplink">Jones told <em>GQ</em></a> about the "Punk'd" star. "He was like, I don't think you're going to be good at this. So - f--- you! He only has nice things to say now - if anything, I should thank him. Because the minute you tell me I can't do something, that's when I'm most motivated."
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.
Lance Armstrong, Ashley Olsen
In 2007, then 21-year-old Olsen was spotted<a href="http://www.huffingtonpost.com/2007/10/31/lance-armstrong-and-ashle_n_70525.html" target="_hplink"> making out with Armstrong</a>, 15 years her senior, at Rose Bar in New York. Yeah, we don't really get it either.
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," <a href="http://rogerebert.suntimes.com/apps/pbcs.dll/article?AID=/20051116/COMMENTARY/511160301" target="_hplink">Ebert wrote in 2005</a>.
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,"<a href="http://www.usmagazine.com/celebrity-news/news/ryan-gosling-exes-sandra-bullock-rachel-were-the-best-girlfriends-ever-2011179#ixzz1wZWnD4oD" target="_hplink"> Gosling told <em>Us Weekly</em> </a>in 2011 (about Bullock and Rachel McAdams, whom he dated afterward). We wonder what current amour Eva Mendes might have to say about that?
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"). <br><br>"I was married, so I gave it a shot,"<a href="http://www.cbsnews.com/8301-31749_162-20029324-10391698.html" target="_hplink"> Clooney told Piers Morgan</a> in 2011. "I've proven how good I was at it, and I just...I'm allowed one."
Courteney Cox, Michael Keaton
The "Friends" star and "Batman" actor dated <a href="http://www.people.com/people/archive/article/0,,20102215,00.html" target="_hplink">from 1989 to 1995</a>. <br><br> (Getty)
Conan O'Brien, Lisa Kudrow
These <a href="http://articles.nydailynews.com/2011-06-29/gossip/29737338_1_phoebe-buffay-improv-groundlings" target="_hplink">two funny people dated</a> 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," <a href="http://xfinity.comcast.net/slideshow/entertainment-forgottencouples/6/" target="_hplink">Kudrow said of their brief romance</a>.
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," <a href="http://www.huffingtonpost.com/2008/04/16/robert-downey-jr-on-datin_n_97012.html" target="_hplink">Downey Jr. said of their relationship</a>.
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."
Alanis Morissette, Ryan Reynolds
Before Blake, before Scarlett, there was Alanis: Reynolds dated fellow Canadian Morissette from 2002 until 2007, when they called off their engagement. Morissette later admitted that her album <a href="http://www.accesshollywood.com/alanis-morissette-talks-ryan-reynolds-breakup-covering-my-humps_article_10455?&__source=rss%257Clatest_news" target="_hplink">"Flavors of Entanglement" was about their breakup</a>.
Carson Daly, Tara Reid; Katie Holmes, Chris Kelin
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," <a href="http://www.nypost.com/p/pagesix/item_YRyKLctrCmIeaFysWHXogP#ixzz1wZUpAuA0" target="_hplink">he said about their romance</a>.
Jack Nicholson, Lara Flynn Boyle
The unlikely couple had an <a href="http://www.popsugar.com/Look-Whos-Back-Together-Again-12062" target="_hplink">on-again, off-again relationship</a> from 1999-2006.
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," <a href="http://www.usatoday.com/life/music/2002/2002-04-15-crow.htm" target="_hplink">Crow said about the actor the same year.
Cameron Diaz, Matt Dillon
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.
Macaulay Culkin, Mila Kunis
It seems like ages ago, but <a href="http://www.huffingtonpost.com/2011/01/03/its-over-mila-kunis-and-macauley-culkin-breakup_n_803457.html" target="_hplink">Kunis split from rumored fiance Culkin</a> only last year, in September 2011. They began dating in 2002.
Sinitta, Simon Cowell
The "X Factor" judge and '80s pop star were once a power couple in the U.K. Even more surprisingly, <a href="http://www.usmagazine.com/celebrity-news/news/brad-pitts-ex-sinitta-dishes-on-his-amazing-body-20112411" target="_hplink">Sinitta also dated Brad Pitt</a> in the late '80s.
Madonna, Dennis Rodman
There are a lot of crazy rumors surrounding this unlikely pair, among them that <a href="http://www.hollywood.com/news/Rodman_Surprised_He_Couldnt_Impregnate_Madonna/3466906" target="_hplink">Madonna desperately wanted to be impregnated </a>by the former basketball star in the early '90s.
Billy Corgan, Tila Tequila
The romance between the Smashing Pumpkins frontman and 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," <a href="http://www.hollywoodlife.com/2011/06/28/shia-labeouf-megan-fox-transformers-dark-of-the-moon/" target="_hplink">the "Transformers" star told <em>Details</em></a> of their failed connection.
Emma Stone, Kieran Culkin
After meeting on the set of 2009's "Paper Man," Stone and Culkin were <a href="http://articles.nydailynews.com/2010-04-07/gossip/27061116_1_emma-stone-kieran-culkin-stars" target="_hplink">rumored to be dating </a>. Stone is now currently dating "Spiderman" co-star Andrew Garfield.
Source: http://www.huffingtonpost.com/2013/04/01/sign-to-break-up-dating-relationship-advice_n_2979510.html
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