I’m not sure what’s more painful to watch—Jon Gosselin going through a midlife crisis or Regis Philbin making uneducated statements (again).

During a pre-taped interview with Kate Gosselin, Philbin openly admitted that he was not a follower of Jon & Kate Plus Eight. Although that reveal should have immediately disqualified him from the conversation, the Live with Regis and Kelly host then proceeded to add his two cents to the divorce matter.

“I just have a feeling, like, I think the separation is going to come to an end, and I think he’s going to come back and he ‘s going to say, ‘Please marry me again,’ and I think you’re going to live happily every after. Now what do you think of that?” Regis asked. Unfortunately for the people who had to watch, the line of questioning didn’t end there.

Watch as Kelly Ripa sits tensely in the background. If you listen closely enough, you could hear the co-host secretly wishing reality fan Anderson Cooper was with her during that segment.

(Make sure to check out our other Awkward TV moments.)