Nicola Sturgeon has said that her conversations with Theresa May during her time as prime minister were "pretty soul destroying".
Scotland's First Minister, speaking at an Edinburgh Fringe Festival event with Iain Dale on Monday, said that Mrs May would always stick to a prepared script and suggested that even light-hearted moments could become awkward.
Mr Dale had asked Ms Sturgeon about the difference in her meetings with Mrs May and those with her successor at Number 10, Boris Johnson, who the First Minister met with last month after he was named as the new Tory Party leader.
"It was a very different experience," said the First Minister of meeting with Mr Johnson.
"I don't want to be too derogatory or pejorative about Theresa May, she's obviously no longer prime minister, but having conversations with Theresa May was pretty soul destroying.
"She would never depart from a script, no matter where you tried to take the conversation.
"I remember in one meeting, going in and trying to think about how can we get this meeting off on a sort of gentler start before we immediately got into the areas where we disagreed.
"And she had, as she often did, a fantastic pair of shoes, a really stylish pair of shoes. And I quite like shoes, so I started the meeting off by saying, 'before we get onto Brexit, fantastic shoes', and in that instant I could see in her eyes, that she didn't have an answer in the script before her for this.
"So it became, what should have been a light-hearted moment, really quite awkward.
"So talking to Boris, at least it was like having a conversation, albeit a bit of a crazy one.
"And you could debate and share views and disagree on things, more than agree, so I'll say that for him. It's a different experience."
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Mr Johnson visited Scotland in his first full week as Prime Minister, which included meetings with Scottish Tory leader Ruth Davidson and with Ms Sturgeon at her Bute House residence in Edinburgh.
The Prime Minister was booed upon his arrival for his meeting with the First Minister, whilst a gesture made by Mr Johnson was seen as an awkward attempt to usher Ms Sturgeon inside the residence.
Ms Sturgeon said that she could not recall her comments to Mr Johnson on his arrival at Bute House, although stated that she did not want to be ushered inside.
"The honest answer is I can't really remember," said Ms Sturgeon of her remarks to the Prime Minister whilst on the steps of the residence.
"I just remember he came up the steps, we did the handshake, we were meant to stand to get a picture taken together and then suddenly behind him came these hordes of people - I think he had about 33 people with him for whatever reason.
"So I think I was just trying to organise everybody. And then the new Secretary of State for Scotland (Alister Jack) came up to me, and I don't mean this as any insult to him, but I didn't immediately recognise him so it was kind of, 'who are you trying to get in my hoose?!
"Then I realised who it was, ushered him in and then I was aware Boris was about to do that thing that guys sometimes do to women and no doubt, you claim it's chivalrous, sometimes it is chivalrous, other times it's patronising, which is to kind of usher you in and put their arm around your back and I decided I didn't really want that to happen."
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Ms Sturgeon added: "Boris Johnson is a Prime Minister that the vast of majority of people in Scotland, had they been given any choice, would not have chosen to give the keys of Number 10 Downing Street to.
"He's a Prime Minister who is intent on taking us out of Europe against our will, looks intent on taking us out without a deal and the catastrophe that would bring about I think is well understood here.
"So I wasn't overly thrilled to be standing on the steps of Bute House welcoming Boris Johnson as Prime Minister."
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