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Owen Wilson and Jessica Simpson Heat Up, Continue to Flirt
Wednesday November 7, 2007

Jessica Simpson and Owen Wilson
Jessica Simpson introduces "Jessica Simpson Collection" at Macy's Herald Square on November 3, 2007 in New York City; Owen Wilson attends the premiere of "The Wendell Baker Story" in Beverly Hills on May 10, 2007.
Kevin Mazur/WireImage.com; Jeff Vespa/WireImage.com

Owen Wilson and Jessica Simpson have known each other for years, but it took Willie Nelson to bring the Texas natives together.

After reconnecting at the Spicewood, Texas set of a Nelson music video on October 15, Simpson, 27, and Wilson, 38, have been spotted getting friendly at bars from coast to coast.

On October 28, the couple hung out in a cabana at The Huntley Hotel in Santa Monica, California. A week later, they were seen again dining at New York's Waverly Inn before heading to the Rose Bar, where a witness tells Us Weekly, "Jessica was touching Owen's arm and flipping her hair." In return, the fellow patron says, "Owen was charming, making Jessica laugh...it felt very date-y."

But are these two singletons looking to settle down, or keep playing the field? A source close to Wilson tells Us, "Owen finds Jessica hilarious, but he's talking to lots of girls." And despite the pair sharing "a natural attraction based on southern values," a Simpson source says Jess is taking things slow. Says one pal, "She didn't think dating would be so hard!"

For more about Owen and Jessica's connection, check out the latest issue of Us Weekly, on newsstands now

Talk to Us: What do you think it means to have southern values?

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