Who Olivia Wilde And Ashlee Simpson Should Date Next

As of yesterday, two lovely famous ladies are once again on the market. First, Olivia Wilde separated from her husband, Tao Ruspoli, the son of an Italian prince. Honestly, we didn’t even realize she was married, but apparently the two met when she as 18. He proposed at Burning Man and they got married on a bus. “We were hippies,” she once told Playboy. “We lived on that bus for months.” Sadly, the party is now over. [LA Times]

And then there’s Ashlee Simpson, who filed for divorce from her husband of two and a half years, Pete Wentz of Fall Out Boy.

After the jump, we pick who these two should date next.Our top picks for Olivia:

  • Olivia was apparently seen chatting with Ryan Gosling at the Golden Globe Awards. We’d be way happier if Ryan were dating her rather than Blake Lively.
  • She played a doctor on TV, while he played a serial killer. Maybe she would hit it off with Michael C. Hall?
  • Megan Fox once famously said, “Olivia Wilde is so sexy she makes me want to strangle a mountain ox with my bare hands.” Maybe Megan would ditch Brian Austin Green for her?
  • Ta da. Jake Gyllenhaal is available. With their sexiness combined, they could rule planets.
  • Since she’s into princes, might we suggest Prince Harry?
  • Since Olivia likes her men a little older, perhaps she’d be into “Black Swan” director Darren Aronofsky, who is also recently single? They both have a certain edge to them.

Our top picks for Ashlee:

  • Deryck Whibley of Sum 41 is a rocker like Pete, and happens to be Avril Lavigne’s ex-husband. I think they might be able to get each other.
  • Normally, we would tell Ashlee to stay far, far, far away from John Mayer because he would get far too much pleasure out of bagging both the Simpson girls. But maybe a romance with John could get Ashlee writing music again?
  • Maybe what Ashlee needs is someone who is the opposite of Pete. I’m thinking she could go a little cougary and go for Zac Efron. They only have a three year age difference.
  • Ashlee doesn’t mind a guy who likes to photograph his private parts. Might I suggest Ray J?
  • Ashlee looks pretty glamorous these days. She and Ryan Reynolds would look super hot together. Plus, he likes blondes.
  • We always liked Ashlee with Ryan Cabrera. Maybe now that he and Audrina Patridge are done, they could give things another try?

Who do you think Olivia and Ashlee should date next?

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