"Until I ran for office we did very well. We had a good relationship. I like Oprah," he said.
He then told a bizarre fib, claiming he had been invited on the Oprah Winfrey Show during its last week on television because he was one of her five "most important" guests.
"Oprah, when she ended her show, had the five most important people. I assume. Her last week," he said.
"Remember her last week. Well I was on her full show in the last week. I think they are trying to burn the tape."
That is quite simply not true.
Mr Trump did appear on the show, along with his wife Melania and five children, on Monday February 7, 2011. Its last episode aired in May of that year.
He has been making this weird claim since at least 2013, when he posted a photo from the appearance on Instagram.
Is Mr Trump genuinely mistaken, or lying? That much is unclear.
The intriguing dynamic between the President and Ms Winfrey has gained more attention amid her political interventions this year.
In February, she interviewed a focus group of 14 voters, half of whom supported Mr Trump in 2016, on 60 Minutes.
The discussion focused on how the voters had come to respect each other, despite disagreeing vehemently on politics.
"When we first met, there were some of you who had said, you know, you'd never been in conversations, certainly engagement, with members of the opposite side. So has that changed for you now?" Ms Winfrey asked.
"Now I'm looking at them as people. Not as you're Trump or not Trump," one voter, named Jennifer, responded.
"This has been an incredible experience and an education for me."
The President took exception to the segment, and posted a cranky tweet accusing Ms Winfrey of being biased against him.
"Just watched a very insecure Oprah Winfrey, who at one point I knew very well, interview a panel of people on 60 Minutes. The questions were biased and slanted, the facts incorrect. Hope Oprah runs so she can be exposed and defeated just like all of the others!" he said.
A month earlier, Ms Winfrey's captivating speech about sexual abuse at the Golden Globes sparked a surge of speculation that she would run for president herself in 2020.
"I want all the girls watching to know that a new day is here on the horizon," she said.
"And when that new day finally dawns, it will be because of a lot of magnificent women, many of whom are right here in this room tonight, and some pretty phenomenal men, fighting hard to make sure that they become the leaders who take us to the time when nobody ever has to say 'me too' again."
Ms Winfrey would undoubtedly be a formidable candidate.
She's a bigger celebrity than Mr Trump ever was before he turned to politics. She has an inspiring life story, having fought her way out of poverty to become a billionaire. And as she proved at the Golden Globes, she's quite the speechmaker.
There is just one problem — Ms Winfrey has repeatedly insisted she has no desire to run.
"I don't want to run, OK? I'm not trying to test any waters. Don't want to go in those waters!" she said last week while campaigning for Ms Abrams.
"I'm here today because of the men and because of the women who were lynched, who were humiliated, who were discriminated against, who were suppressed, who were repressed and oppressed, for the right for equality at the polls."
She urged voters, particularly women and African-Americans, to make the effort to vote.
"For anybody here who has an ancestor who didn't have the right to vote, you are dishonouring your family. You are disrespecting and disregarding their legacy, their suffering and their dreams when you don't vote," she said.
Vice President Mike Pence reacted to the speech by mocking Ms Abrams for relying on her "liberal Hollywood friends" for support.
"This ain't Hollywood. This is Georgia," Mr Pence said, apparently forgetting his own side had just elected a reality TV star to be president.
Ahead of Mr Trump's appearance in the state today, Ms Winfrey was the target of a "vile" underhanded tactic. An unknown number of voters received an automated, racist robocall from a white supremacist group, which impersonated her.
Both Ms Abrams and Mr Kemp condemned it.
Despite Ms Winfrey's intervention, Mr Kemp is likely to emerge as the winner in Georgia. Polls have shown him in front by double digits, and the state usually leans Republican.
But it might not be the last time she and Mr Trump go head-to-head.
