She asked him to leave, attempted to give back the phone and some of the money, and refused to have any further dealings with him.
He repeatedly tried to contact her and hired a private investigator to find her, leading to the sex worker seeking a five-year restraining order against him, which was reduced on appeal to one year.
In the latest court action, the man was pursuing a civil claim for breach of contract and unjust enrichment, defamation, malicious prosecution of a civil proceeding and abuse of process, breach of confidence, breach of privacy, and breach of the Consumer Guarantees Act.
The claim was stuck out in the District Court, with the judge calling it an abuse of process, frivolous and vexatious.
The High Court also rejected the action, saying none of the claims could succeed.
The man then applied for leave to appeal to the Court of Appeal, claiming the High Court judge was biased against him, had not addressed his concern that the District Court judge was also biased against him, and had erred in law.
The Court of Appeal found there was no substance to allegations of bias, and no identifiable error of law.
Even had there been an error, the court found there was no justification in a further appeal.
"As well, even if there were an arguable ground of appeal, we are satisfied that leave should be refused on the grounds that there is no issue of fact or law of sufficient importance, public or private, to outweigh the cost and delay of a further appeal."
The man was ordered to pay costs to the woman.