Awkward might not be the start of it. Yet a dinner with Boris Johnson, Theresa May and David Cameron was the top lot at the Conservative party's annual summer party in London on Monday night.
The prospect of sitting down for supper with Mr Johnson, whose behaviour as a troublesome backbencher put paid to the careers of his predecessors Mrs May and Mr Cameron when they were in Number 10, might have put off many people.
But not - it seems - the Tory party's funders, with one unnamed donor bidding ￡120,000 for the honour of attending the apparent “dinner from hell”. Perhaps they might have brought their own box of popcorn in hand to see how they got on.
The lot was titled the "Dinner of the Century" to avoid having to ask the only other surviving Tory Prime Minister - Sir John Major, who was PM between 1990 and 1997.
"We assumed he wouldn't want to have dinner with Boris," one Tory source said of Sir John, who has been a strident critic of Mr Johnson over Brexit and other issues.
A spokesman for Sir John confirmed he was not invited, but told The Telegraph: "If he had he would have declined – as he has for all such requests in the past.
'No control' over bids for 'access'
"There is no control over who might bid for 'access' and, for that reason, we believe it is best to steer clear. There are other ways to lend support."
Other auction lots included a safari in South Africa, a wine tasting trip, a shooting weekend on an estate in Scotland and a box at a Premier League football match.
In all the Conservatives raised over ￡500,000 from the evening for the party's burgeoning efforts to raise money to pay for dozens of campaign managers at the next general election.
Lord Leigh, the long serving treasurer, raised ￡40,000 by asking the guests to stay standing if they could donate another ￡500 each.
Around 300 guests, in lounge suits and formal attire enjoyed a starter of salmon tartare followed by beef with asparagus mash, with passion fruit meringues for dessert.
With the striking rail protesters at the door, the peer - who has been treasurer since Mr Cameron was Opposition leader - dropped his usual jokes to make a direct pitch for cash.
Free drinks in Kyiv
“If you give money to the Conservative Party, and you go to any bar in Kyiv and tell them you are supporting Boris, you are guaranteed a free drink," he said.
Two dozen Cabinet ministers were on the 30 tables, each seating 12. The only obvious absentee was Alok Sharma, who is overseas on Government business.
Mr Johnson was there for 30 minutes, shaking hands and giving a short speech, despite having an operation on his sinuses earlier in the day.
The Prime Minister's speech - delivered to the distant sound of protesting union officials outside in Kensington - was described as a "tour d'horizon" which name checked virtually all of the Cabinet ministers.
He joked that he was only there against doctors' orders because he had had "nose job" earlier in the day adding: "But Lynton Crosby has told me to ask for my money back."
'The biggest cost of living is tax'
Mr Johnson made clear he was concerned about tax levels, telling guests that the "biggest cost of living is tax", without saying what he would do about it.
Mr Johnson made way for Michael Gove, the Levelling Up secretary, who observed that the party was made for the V&A, with its galleries of fashionable clothing.
In contrast, Mr Gove said, Labour was more suited to the National History Museum, and the Liberal Democrats to the Parthenon "because they have lost their marbles".
Party officials were delighted with the evening which was aimed at establishing a group of up to 50 campaign managers across the country.
One witness said the chanting from the entrance outside "focused minds on what is at stake at the next general election".
The source said: "We are well on our way with that with dozens already working. It is an important part of the ground war strategy that party chairman Oliver Dowden and his team set out at the away day for MPs."