The presumptive Republican nominee sat down with the Fox News anchor during a primetime special of "Megyn Kelly Presents."
For all the incendiary comments that have been emitted from Trump's twitter feed, he begrudgingly admitted that he had some regrets. Kelly asked if he regretted any of his comments about Sen. John McCain or Carly Fiorina's face.
"Uh, yeah, I guess so, but you have to go forward...to look back and say, "Gee whiz, I wish I didn't do this or that," I don't think that's good... I don't even think- In a certain way, I don't even think that's healthy," Trump said.
Trump also admitted to other moments of contrition. Kelly asked if he was regretted anything since that first debate.
“Absolutely I have regrets. I don't think I want to discuss what the regrets are, but absolutely. I, I could have done certain things differently...I could have maybe used different language, uh, in a couple of instances,” Trump said.
But he added, “Overall, you know, I have to be very happy with the outcome... And I think if I didn't conduct myself in the way I've done it, I don't think I would have been successful actually."
Of course, the two discussed their "little difficulty" as Trump called it.
Their feud first began last year, back in August at the first Republican debate. Kelly, as moderator, asked Trump about comments he had made to women, saying he "“called women you don't like fat pigs, dogs, slobs and disgusting animals.”
During the interview, Trump maintained that he though Kelly's question was "unfair" but admitted that she was justified.
"I don't really blame you because you're doing your thing. But from my standpoint, I don't have to like it," he said. And he refused to apologize for insults hurled at her via twitter, such as "bimbo" and "lightweight".
"Not the most horrible thing... Over your life, Megyn, you've been called a lot worse, is that right, wouldn't you say?" Trump asked, calling his tweeting "a modern day form of fighting back".
In August, Trump demonstrated that in full force, beginning what would be the first in a barrage of tweets directed against her.
Trump continued to criticize the Fox News host the day after the debate, telling CNN, “There was blood coming out of her eyes, blood coming out of her wherever.”
“I just don't respect her as a journalist,” he continued. “I have no respect for her. I don’t think she’s very good. I think she’s highly overrated."
In an Aug. 9 interview on ABC News’ “This Week With George Stephanopoulos,” Trump said that he meant Kelly’s nose when he said “wherever,” and he did not apologize for the comments.
On Tuesday, Trump wouldn't say if he would stop tweeting insults as president, but did reveal a bit of his personality that seems to bring his habitual hurling of insults into view.
Kelly asked Trump if he had ever been wounded. While the New York businessman would only mention his brother's death, he did add one thing. "When I'm wounded, I go after people hard, okay? And I try and "Unwound" myself."
But even with a touch of introspection, the night would not be complete without Trump doing what he does best; in true fashion, he livetweeted the entire interview, mostly retweeting and responding to compliments.