Donald Trump is notorious for never saying he's sorry, yet, there was one tweet that even he regrets.
It all started during the live broadcast of the 2014 Academy Awards when actress Kim Novak made a rare public appearance at age 81.
Once among Hollywood’s great beauties, some viewers, including the future president of the United States, were taken aback by her appearance.
Watching from home, Trump tweeted, "I’m having a real hard time watching... Kim should sue her plastic surgeon!"
Novak had lived a reclusive life for many years in a remote town in Oregon. She was reluctant to appear at the Oscars that year, but friends convinced her to accept the invitation.
She was backstage at the Dolby Theater when she read Trump's tweet and was devastated, so much so that she didn't leave her home for months.
It wasn't until Trump became a candidate for president in 2015 that he finally apologized.
"I would have preferred I didn't send it," he told The New York Times. "That was done in fun, but sometimes you do things in fun and they turn out to be hurtful, and I don't like doing that."
"It is too bad bullies don't think before they open their mouth," Novak told Inside Edition in 2015.
When asked by Inside Edition if she accepted Trump's apology she said "Sure, why not?"
Trump has come under heavy criticism for what many consider to be petty and vindictive remarks aimed at certain high-profile women.
"You could see that blood was coming out of her eyes, blood coming out of her wherever,” where his famous words about then-Fox News anchor Megyn Kelly.
He also poked fun at former GOP candidate and one-time rival Carly Fiorina when he was caught during an interview with Rolling Stone in early 2016 saying: "Look at that face! Would anyone vote for that?"
Then in the fall of 2016, the notorious Access Hollywood tape where he was caught on a hot mic telling Billy Bush that you can grab women by their “p****.”
He later apologized and called it “locker room talk.” Bush was fired after the tape was leaked.
This week, Trump blasted Mika Brzezinski in a series of tweets, claiming she was "bleeding badly from a face-lift” when she and Morning Joe co-host Joe Scarborough went to Mar-a-Lago around New Year’s Eve.