Donald Trump has had his fair share of feuds since he became president, but his shots at Oprah Winfrey seem a bit strange considering the two used to be friends. She was targeted after many thought she was going to run against him in 2020, even though she has since tried to dispel those rumors.

So why is he still going after her now and how has she responded to all this? Here’s a little more about their past relationship and their current feud.

In 1998, Trump appeared on Winfrey’s talk show and spoke then about a possible presidential bid someday. Then, in 1999 while on Larry King Live, Trump revealed that he would want Winfrey to be his running mate.

“I love Oprah,” he said. “Oprah would always be my first choice … I’ll tell ya, she’s really a great woman, though. She is a terrific woman. She’s somebody that’s very special. I think if she’d do it, she’d be fantastic. I mean she’s popular, she’s brilliant, she’s a wonderful woman.”