Monday, July 14, 2014

  • Kathy Griffin

    Kathy Griffin and...

  • Quentin Tarantino

    Quentin Tarantino!

    (AP Photo/Virginia Mayo)

  • Kathy Griffin & Quentin Tarantino

    Kathy Griffin & Quentin Tarantino

    The fiery comedian and the Academy Award-winning director went on a date sometime in the early to mid '90s. On the fleeting couple's one amorous evening, Griffin bluntly said she and Tarantino "did everything but penetration." Evidently, one night was enough for Tarantino, who subsequently gave Griffin a small speaking role in his 1996 Palme d'Or-winning film, Pulp Fiction.

    (Photo by Kevin Mazur/WireImage)

  • Katie Couric

    Katie Couric and...

    (Photo by Evan Agostini/Invision/AP)

  • Larry King

    Larry King!

    (Photo by Vince Bucci/Invision for AARP Media/AP Images)

  • Larry King & Katie Couric

    Larry King & Katie Couric

    Unlike many of you out there, I get this relationship. We're all human, we all get lonely, and we all have needs that can only be fulfilled by an overly avuncular Jewish man in suspenders. Years later, Couric revealed that King practically invited himself back to her hotel room. Her response? "No, thank you, Larry." Speaking for the human race, I think we can all be glad.

    (AP Photo/Charles Sykes)

  • Lisa Kudrow

    Lisa Kudrow and...

    (Photo by FilmMagic/FilmMagic)

  • Conan O'Brien

    Conan O'Brien!

    (Photo by Dimitrios Kambouris/Getty Images for Turner)

  • Lisa Kudrow & Conan O�™Brien

    Lisa Kudrow & Conan O'Brien

    The two dated right before each rose to national prominence, but stardom didn't bode well for their budding romance. It was a simpler, happier time for O'Brien, an Emmy Award-winning writer for The Simpsons, and Kudrow, a Groundlings-trained comedic actress making the rounds in Hollywood. The couple broke up shortly after O'Brien was picked up by NBC to host Late Night and Kudrow was cast as Roz Doyle on Frasier.

  • Joan Rivers

    Joan Rivers and...

  • Robert Mitchum

    Robert Mitchum!

  • Joan Rivers & Robert Mitchum

    Joan Rivers & Robert Mitchum

    The acerbic jewess and the handsome pothead had a tryst after Mitchum appeared on The Tonight Show while Rivers guest hosted for Johnny Carson. According to the comedienne, the two met for drinks in Malibu after taping, where she "practically put (her) legs on the table." Though Rivers was married with a child (Melissa Rivers), she admits to contemplating leaving her husband for the handsome actor, saying she would've left with him in a second. "I would've said, 'Melissa who?'"

  • Carmen Electra

    Carmen Electra and...

  • Dennis Rodman

    Dennis Rodman!

    (AP Photo/Kim Kwang Hyon)

  • Carmen Electra & Dennis Rodman

    Carmen Electra & Dennis Rodman

    Why this celeb couple made the list should be obvious to all. They were married at the Little Chapel of the Flowers in Las Vegas and arrested for domestic violence all within the same month. The union lasted just six months and was a clean break for both parties, though mostly for Electra who refuses to speak of their relationship. For those who miss the antics of the cross-dressing Chicago Bulls star, Rodman can be seen playing house with the new dictator of the Democratic People's Republic of Korea, Kim Jong-Un, and in the season finale of the HBO series, Vice.

  • Lisa Marie Presley

    Lisa Marie Presley and...

    (Photo by Carlo Allegri/Invision/AP)

  • Michael Jackson

    Michael Jackson!

  • Lisa Marie Presley & Michael Jackson

    Lisa Marie Presley & Michael Jackson

    Jackson was most forthcoming about his relationship with Presley, more than anyone expected or could stomach. To wit, at the 1992 VMAs when Jackson, walking hand in hand with Presley, proudly declared, "no one thought this would last." You know what, you're right Michael, no one thought it would last and it didn't. The two split shortly after this public display of affection as the arranged relationship between the reigning King of Pop and the King of Rock & Roll's heiress was squeezed of its last PR juice.

    (AFP/Getty Images)

  • Lindsay Lohan

    Lindsay Lohan and...

    (Photo by Scott Roth/Invision/AP)

  • Samantha Ronson

    Samantha Ronson!

    (Photo by Mark Von HoldenInvision/AP)

  • Lindsay Lohan & Samantha Ronson

    Lindsay Lohan & Samantha Ronson

    Since LiLo has now seemingly gone the sober route—following her 90-day stint in rehab and subsequent teary-eyed interview on Oprah's Next Chapter—I'm nostalgic for her coke sniffing, party girl days. This era was not only fraught with booze and illicit drug use, but for a while in the late 2000s, it also involved a lesbian relationship between Lohan and DJ Samantha Ronson. The tumultuous union played out on TMZ, and chronicled the child star's descent into DUI madness. While this relationship is seemingly in Lohan's past, we can still rejoice at the glory that once was.

    (AP Photo/Evan Agostini)

  • Jennifer Aniston

    Jennifer Aniston and...

  • Jon Stewart

    Jon Stewart!

    (Photo by Theo Wargo/Getty Images for Spike TV)

  • Jennifer Aniston & Jon Stewart

    Jennifer Aniston & Jon Stewart

    This awkward pair went out on a date, of sorts. To Stewart's recollection, they met at an Italian restaurant and Aniston brought several friends, so the comedian could get to know her clique. For Aniston, she was out with a group of her friends and Stewart tagged along. Whoever was right, all I can say is that, though not as tall, Stewart would have never broken her heart the way Pitt did. Your loss, Jen.

  • of your parents with an ex-boyfriend or girlfriend? These old and bizarre entanglements are not just the remnants of our seemingly banal forbearers; the celebrity glitterati also have their share of romantic skeletons in the proverbial closet. Sharon Osbourne recently revealed that she briefly dated Jay Leno when she first moved to America. While both share appropriately high-pitched vocal tones, I think I speak for everyone when I say, "WHAAAA?!" Here to let the cat out of the bag is

    both old and new. Gird your loins, and read above.

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