Some pictures of Jessica Simpson out for dinner in NYC, carrying a huge handbag around with her.

Some pictures of Jessica Simpson arriving at NYC airport.

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!”

Some pictures of Jessica Simpson at the 2007 BMI Country Awards.

Some pictures of Jessica Simpson hanging out with Mandy Moore at 11TH Annual ACE Awards.

Some pictures of Jessica Simpson outside LAX Nightclub wearing a long coat covering her white top and blue jeans.

Some pictures of Jessica Simpson making an appearance at Macy’s Herald Square department store to promote her latest shoe line and handbag designs.