Jessica: Who's She Rollin' With?

Friday August 25, 2006 06:00 AM EDT

Jessica Simpson

Michael Caulfield/WireImage

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Jessica Simpson sure gets around. Two days after hosting the Teen Choice Awards in L.A. the pop diva jetted home to the Lone Star State to be a special guest at the Interskate Roller Rink in Lewisville, Texas.

The singer – who filmed her "A Public Affair" video on roller skates – schmoozed (She "was very laid-back and casual," Interskate owner Luther Bernstein tells us) and spent several minutes chatting on the side of the rink with a radio listener who had won a skate with Simpson. When the girl admitted that she didn't know how to skate, Simpson had no problem with just talking – she was no whiz on four wheels either while shooting her video.

During the night, the singer treated KISS deejay Billy the Kidd with a birthday serenade over the P.A. system. She sang it "in a sexy Marilyn Monroe voice," says Bernstein.

Jake: Love Connection?

While Matthew McConaughey and Lance Armstrong have been making the Miami nightlife rounds, pal Jake Gyllenhaal has been partying in the Big Apple.

Jake Gyllenhaal Photo by: Winslow / Klebanow / Splash

The actor recently hit New York City hot spot Butter, where he made his way to Jamie-Lynn Sigler's booth, and with a Corona beer in hand, he rocked out to Fergie's "London Bridge." Later, he started dancing with one of the Sopranos star's brunette friends. The two whispered and laughed with each other for the rest of the night and, at one point, she plopped herself on Gyllenhaal's lap. Before leaving with Sigler at around 3 a.m., the pal and Gyllenhaal whipped out their cell phones and started typing numbers. They also exchanged a long hug good-bye.

That didn't end the fun for Gyllenhaal, who danced to Madonna's "Like a Prayer" (even doing a bit where he crossed himself) and did the limbo with a few women. So, how low can he go?

• By DARLA ATLAS and LESLEY MESSER