Boyd claims that when he asked Sir John to pay for his dinner, the Prime Minister said "absolutely".
Sir John denied that at the time and has repeated that denial in a sworn statement to the court. He said he responded with "yeah lots of people say that".
When leaving the restaurant, Boyd told Green Parrot staff that Key's table would be paying his bill.
The Crown says a "dispute" arose at the front desk, and eventually a diplomatic protection officer approached to tell them the Prime Minister wasn't paying the bill.
As they were becoming concerned about the disturbance, the officer then took Boyd outside. He was detained and eventually arrested on suspicion of theft of the meal he had eaten.
A charge of breach of bail was added later, as officers suspected Boyd had breached his bail conditions by drinking alcohol.
Police withdrew the charges some days later.
Boyd is bringing his cases under a mix of common law and Bill of Rights claims, saying he shouldn't have been arrested, and that the force used to arrest him was excessive.
He is also bringing a separate charge of excessive force being used to arrest, after Boyd was bitten by a police dog in the Botanic Gardens, while being sought for arrest in relation to a domestic assault.
Boyd is claiming $10,000 for assault and detention after his arrest at the Green Parrot, $10,000 for being arrested for breaching bail conditions without reasonable basis, and $10,000 for damages for the dog bite.
The trial is now before the Wellington District Court judge.