Jessica Simpson and Owen Wilson seem to be exhibiting all the classic signs of courtship, complete with tress tossing and joke telling. According to Us Weekly, the bumpy-beaked, blond Texans were flirting up a storm during a night out in New York last week, a rendezvous that came just days after their meet-up in Los Angeles. "Jessica was touching Owen's arm and flipping her hair," an observer tattles to the magazine, with another eavesdropping bystander chiming in, "Owen was charming, making Jessica laugh ... it felt very date-y." Still, a Simpson confidante says the unlucky-in-love starlet is proceeding with caution, despite sharing "a natural attraction based on southern values" with Wilson, whatever that means. Exclaims another Jess pal, "She didn't think dating would be so hard!" As for the on-the-mend Butterscotch Stallion, he continues to gallop up to other fillies. "Owen finds Jessica hilarious," a friend of the funnyman explains to Us, "but he's talking to lots of girls." True enough. E!'s Ted Casablanca reports an Evian-sipping Wilson spent close to two hours chatting with a "pretty blonde" during a shindig earlier this week at Manhattan hot spot Butter. They purportedly left together after their extended tête-à-tête.

In related news, Jessica ex John Mayer also turned up at the Butter bash, where a spy tells Ted "he was very flirty with a cute brunette." No word on whether the dark-haired gal in question was "Friday Night Lights" cutie Minka Kelly, whom he's recently been linked to. But Mayer, like Wilson, appears to be keeping his options wide open. The New York Daily News claims the seemingly silver-tongued crooner was locking lips with a "blonde bombshell" at a New York soiree last week, and had an answer at the ready when his saliva-swapping partner achieved a moment of clarity and asked, "But how do I know you really like me?" Just call him Mayer McCheese, because he supposedly reassured her by cooing, "Because I'm going to do this," and promptly pulled her face in close for more tonsil polishing.

The serious ick factor brought on by Lance Armstrong and Ashley Olsen's recent cuddle-bunnies may be mercifully fleeting. "Lance is a candidate for a midlife crisis," an insider scoffs to Us Weekly of the unseemly dalliance, with another source sniping, "Next week, he'll be on to someone else." Whatever happens, the Tour de France champ (and divorced dad of three) appears to be making the most of his fling before it's flung. The magazine says Armstrong and Olsen were acting "very flirtatious" at New York's Rose Bar on Oct. 29. The following evening, the ooky twosome, who were reportedly both staying at the swanky Soho House (but in separate rooms), enjoyed "Young Frankenstein" on Broadway before dinner and drinks at the Waverly Inn.

Did Sienna Miller bust a gut when Rhys Ifans asked her to stick around as long as they both shall live? That's the tale being told by the London Daily Mirror, which says the starlet misinterpreted the actor's earnestness as he warbled a prose proposal he'd penned titled "Marry This Misfit." (In Sienna's defense, we, too, would have been rolling over such purported declarations as, "I bleed for you.") "She fell about laughing, but soon realized Rhys was serious," a mole tells the tab. "While she didn't give him an answer straight away, she's since been thinking about it more and more." Miller is no stranger to proposals, although her ex, Jude Law, went the more traditional route when he popped the question on Christmas Day 2004, presenting her with a gold band dotted with nine diamonds. And we all know how that worked out.

All you "Office" fans secretly hoping for a real-life Jim and Pam romance, just give it up already. The New York Daily News spied John Krasinski "canoodling" with on- and off-screen ex Rashida "Karen" Jones at a post-"SNL" party last week, the second time in six months they've been seen cozying up. The paper also caught the sometime squeezes looking thisclose at a May screening of "Shrek the Third."

Next: A Boy and a Girl for J.Lo and Marc?