"I'll just organise my paperwork here," Craig continued.
"We texted each other about all sorts of things, didn't we?" he asked MacGregor. "Around the world and back, so to speak."
Sitting behind Craig, MacGregor's lawyer Hayden Wilson said: "What does that mean?"
Craig quipped: "Everything under the sun."
"Work, health, diet, finances, relationships, family, spiritual things, things about God," he listed.
Craig and MacGregor are suing each other for defamation over what happened during the fallout from New Zealand's 2014 general election and the eventual end to Colin Craig's political career.
MacGregor was hired as Craig's press secretary in 2011 and they soon developed a close relationship, the High Court has heard this week.
However, things soured in the lead-up to the 2014 general election and Craig, an accountant by trade, told his wife Helen he thought MacGregor "appeared to be having a meltdown".
Just two days before the election MacGregor quit as press secretary.
MacGregor later filed a sexual harassment complaint against her boss.
A confidential settlement between him and MacGregor was reached in May 2015, however, it soon became public.
In 2016, Colin Craig was ordered to pay MacGregor more than $120,000 by the Human Rights Review Tribunal after it ruled he breached the confidentiality agreement in interviews with the press.
Craig argues MacGregor defamed him three times.
Firstly by what MacGregor told New Zealand Taxpayers' Union founder Jordan Williams, then in a media release by MacGregor in June 2015, and also in a tweet on the same day.
"I have never defamed him," MacGregor said yesterday.
"I told a small group of friends in confidence that I had been sexually harassed by Colin Craig ... I did not broadcast it."
MacGregor's lawyers, Linda Clark and Wilson, claim she was defamed in four instances.
Twice in two press conferences held by Colin Craig, in a booklet titled Dirty Politics and Hidden Agendas which was delivered to 1.6 million Kiwi households, and in a letter to Conservative Party members.
Craig defamed MacGregor by alleging she made false claims of sexual harassment, the now public affairs manager's lawyers argue.
Craig withdrew his claim for damages on Monday - day one of the trial - after he became aware MacGregor could not pay him if he won the case.
He also has had defamation proceedings against, what he calls, the trio of "schemers".