Lisa Kudrow And Conan O??Brien
[ranking: 32]
Conan O'Brien was a writer for Saturday Night Live and Lisa Kudrow was a comedian in Los Angeles. Their larger-than-life kooky personalities seem like an odd match now, but at the time, they had a lot in common.
??He was really smart, really funny and he thought I was funny," Kudrow said, adding the two "found we were better as friends."
Moby And Natalie Portman
[ranking: 22]
This pair briefly dated in 2001, and Natalie Portman??s fandom was not happy about it. This was not the droid they were looking for. In a Spin interview, Moby shed some light on how people reacted to the relationship.
??I guess in some people??s eyes, [nerds] might be mildly sexy - and, as a nerd, I??m certainly happy to enjoy some of the effects of that - but as far as the very brief affair I had with Natalie, it??s made me the target of a lot of nerd wrath," he said. "You can??t date Luke Skywalker??s mom and not have them hate your guts.??
Courtney Stodden And Doug Hutchison
[ranking: 2]
Doug Hutchison wasn??t much of a celebrity until he married a 16-year-old virgin. The character actor met the highly ambitious Courtney Stodden, 35 years his junior, online. After a bit of a courtship, her parents gave the actor consent to marry their daughter. Stodden and Hutchison wed in 2011. They split up in 2013 due to their age gap, but it didn??t last long. They got engaged in 2014, with Stodden saying that she had given other men a try and missed her husband.
Besides the age thing, it was Stodden??s hilarious behavior during an ABC interview that went viral. Stodden??s dad is four years younger than Hutchison.
Hayden Panettiere And Wladimir Klitschko
[ranking: 37]
This odd celebrity couple was met with a lot of noise about their height difference - she??s 5?? 2?? and he??s 6?? 6?? - as well as why the actress would choose heavyweight boxing champion Wladimir Klitschko as her boo. For Hayden Panettiere, it was a no-brainer.
"I know that I'm small, but he's large," she said in 2013, the year they got engaged. "That's how we met. I said, 'You're huge.' He said, 'You're tiny.'" The pair broke off their engagement in 2018.
Katie Holmes And Jamie Foxx
[ranking: 31]
Dawson's Creek star Katie Holmes and Django Unchained star Jamie Foxx began dating under the radar in 2013. In 2015, Holmes was caught wearing a disguise to meet Foxx at a hotel. They had been caught by paparazzi holding hands years earlier, and sources said their friends and family knew about the relationship.
But the two had yet to go public when Holmes was spotted in a wig in September 2015.
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Roger Ebert And Oprah Winfrey
[ranking: 9]
Their two dates didn??t turn into a long-term relationship but they did make Oprah the reigning queen of daytime TV and a living legend. Ebert recounted how he advised her on taking a deal with either ABC or King World. On their date at Hamburger Hamlet, Ebert did some simple math and showed Winfrey just how much a syndication deal with King World would make her.
She made up her mind in 10 seconds: ??I??m going with King World.?? They may not have waltzed down the aisle, but we do have Ebert to thank, in part, for Oprah.
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