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The US president said that sometimes when he tweets he gets telephone calls asking if he really just said what was being reported, leading him to realise there was something wrong.
Mr Trump even indicated he wished he waited longer before hitting send, talking about when he would write heated letters and then be pleased he did not post them.
The remarks came as Mr Trump gave an interview to David Portnoy, the founder of the sports and pop culture blog Barstool Sports who has an avid online following.
Mr Portnoy asked if the president ever sent a tweet and then the next day woke up and thought, “Oh man, I wish I didn’t send that one out”.
Mr Trump responded: “Often. Too often. You know it used to be in the old days before this you’d write a letter and you’d say ‘this letter’s really bad’.
“You’d put it on your desk and then you go back tomorrow and you say, ‘Oh, I’m glad I didn’t send it’. Right?
“But we don’t do that with Twitter, right? We put it out instantaneously, we feel great. And then you start getting phone calls. ‘Did you really say this?’
“I say, ‘What’s wrong with that?’. And you find a lot of things. You know what I find? It’s not the tweets, it’s the retweets that get you in trouble.”
The remarks came just after Mr Trump had made his more common response - that he likes Twitter because it allows him to get his message out unfiltered.
It suggests that the president, who rarely admits making mistakes in public, sometimes privately regrets issuing certain tweets.
Mr Trump’s use of Twitter is central to his communication approach as president. He writes many of the tweets himself, though sometimes aides pre-plan messages.
They have caused countless rows in his three-and-a-half years in office, sometimes creating friction with foreign leaders or triggering fresh debates about the language Mr Trump uses.
An early attempt inside the Trump administration to create a committee to vet every one of Mr Trump’s tweets before it went out was rejected by the president.