Regis Philbin Gets Awkward with Kate Gosselin

Can we say Awwwwkward? (AP Images)"]

Regis Philbin is a bit of a crusty old dude. With humor circa 1955, his schtick just ain't that funny anymore so he relies on silly quips that aren't really quips at all, just awkwardness. Sadly, people laugh because they're uncomfortable, not because Regis is funny. That said, he decided to joke (or try to joke) about Kate Gosselin's recent and highly publicized split from her husband Jon Gosselin when she appeared for a taping of Live with Regis and Kelly.

The New York Daily News is reporting that things went really weird when Philbin asked Gosselin whether or not she thought she'd get back together with Jon (who has since gotten earrings, is shopping for a new porsche and banging a 22-year-old).

"I can't and won't answer that," Kate said, obviously uncomfortable. "I keep certain things private, and that's one."

Philbin should have picked up on the social cue that he had gone too far, but alas, the 77-year-old didn't.

"I think you will get back together and live happily ever after," Philbin went on. "I think everything is going to work itself out -- he'll say he's sorry, that he loves you and everything will be good."

Cut to awkward silence as they went to commercial break. Well, Regis and Kelly won't be winning an Emmy this year, but that won't stop you from betting on the Emmys, will it?