“I am more pessimistic than at the start of our dinner”, European Commission president Jean-Claude Juncker told Prime Minister Theresa May on his way out of 10 Downing Street. It was late in the evening of 26 April 2017, nearly a year after the British people had voted to leave the European Union. A few weeks earlier, May had notified President Tusk of the European Council of the UK's departure planned for March 2019. The conversation between the prime minister and the Commission president started pleasantly. Juncker is good at small talk and putting people at ease. Michel Barnier, his Brexit negotiator, and his counterpart David Davis reminisced briefly about the 1990s when they represented France and the UK in the preparations for the Treaty of Amsterdam. By the time the EU leaders had signed the Treaty in 1997, French and British voters had kicked both politicians out of office and Tony Blair overturned John Major's opt-out of the EU's “social chapter”. Blair wanted to put the UK back “at the heart of Europe”.

Top British and EU aides attended the dinner conversation but purdah rules barred May's closest advisers and architects of her Brexit approach, Nick Timothy and Fiona Hill, from participating. Eight days before, May had come back from a hiking holiday in the Swiss Alps and announced early elections to bring “unity here in Westminster” and “make a success of Brexit”. Although the UK was now officially in an election campaign, Juncker and Barnier still went to London, as it was high time to sound out the UK's intentions. Three days later, the 27 EU leaders would meet in Brussels at a special Brexit summit for the adoption of their negotiation guidelines with the principles that would inform all EU positions.

The Downing Street dinner was the first occasion to compare the EU's approach with UK thinking. The elections would in any case not change much, people in Brussels thought, and most probably lead to a more effective Tory government until 2022, with a larger majority. Juncker's team liked that prospect. Tony Blair, whom Barnier met in Dublin on 11 May, predicted a landslide victory for May and urged Barnier to keep all options open nevertheless.