Five Really Weird Celebrity Dates

Cupid Definitely Misfired with These Short-lived Celeb Love Connections

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Five Really Weird Celebrity Dates
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(Katie Couric)

Talk about an odd couple!

Daytime darling Katie Couric recently revealed to Jimmy Kimmel that she once went out on a date with CNN alum Larry King -- and she had to turn his advances down! Katie told the late night host all about her night out with King more than 25 years ago, which included dinner at an Italian restaurant where her date -- who was 23 years her senior-- ordered veal poached in chicken stock because he had just had a quadruple bypass.

She also dished that King drove her back to his place and tried to make a move on her, saying "the whole situation was out of a bad Lifetime movie."

If you think a Katie/King love connection sounds bad, check out these other really weird celeb dates.

Oprah Winfrey and Roger Ebert

Oprah Winfrey's unlikely romance with film critic Roger Ebert didn't pan out -- they only went out on two dates in the 1980s -- but he did leave her with some career advice that was life changing. On the Queen of Talk's 20th anniversary special she revealed that while on her first date with the Roger at a hamburger joint, he convinced her to let her then-local talk show go into syndication. His persuasive method? He crunched the numbers on a Hamburger Hamlet napkin and showed her the tally. For their second date Roger took the rising TV star to see the Count Basie Orchestra, but Oprah had to cut out early so she could get up at 5 a.m. to host her new syndicated talk show!

LeAnn Rimes and Tiger Woods

Long before they married other people (and subsequently cheated on their spouses), pro golfer Tiger Woods and country music star like LeAnn Rimes made some music together. According to Us Weekly, the unlikely pair went out a few times, with a source saying: "They hooked up and everything. Tiger was really into her. He likes those blondes!" Rimes' protective dad put the kibosh on the romance though, saying his then-teen daughter was too young for Woods, who was seven years her senior.

Chelsea Handler and 50 Cent

Comedienne Chelsea Handler long denied a romance with rapper 50 Cent, despite the fact that the two were spotted getting cozy at a New Orleans bar in 2010. But the "Chelsea Lately" host eventually came clean, admitting that she and Fiddy once dated "very casually."

"I was sampling, kind of, the atmosphere, seeing what was out there," Handler said during an interview with Piers Morgan. She also revealed that the rapper sent her lavish gifts and she returned some of them.

"I don't really like when men buy me ridiculous gifts, especially when I don't know them well," she said. "I can buy my own gifts… I really don't like gifts from rappers in general, since I'm not a hooker."

Lance Armstrong and Ashley Olsen

Now here's a scandal! In 2007, 21-year-old child star-turned-fashion entrepreneur Ashley Olsen was spotted getting hot and heavy with 36-year-old pro cyclist Lance Armstrong. According to the New York Post's Page Six, the two hooked up at the Rose Bar at the Gramercy Park Hotel where they drank red wine and were "making out all night." The odd couple reportedly left together around 2 a.m., but the romance fizzled. Now if only he'd had a friend for her sister...

More From This Contributor:

5 Bizarre Celebrity Love Notes

Brad Pitt's Chanel Ad: Other Famous Faces of Chanel

The Top 10 Moments From Oprah's David Letterman Interview

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