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!”