Lester accused Calvert of being seen with a journalist and trying to undermine Day's appointment. He threatened to take her portfolios off her.
That night he came over to her house with the bottle of wine.
On another occasion in 2019 Lester told her he wouldn't know how he would be able to work with her over the next triennium if she supported Andy Foster's notice of motions around the controversial Shelly Bay development, according to Calvert.
Lester cannot recall the conversation.
He denies ever telling Calvert he'd "go hard" against her if she didn't support the Let's Get Wellington Moving indicative package.
Lester said Wellingtonians weren't interested in "petty squabbling between councillors" and he would not tolerate disrespectful behaviour.
Calvert has admitted she apologised over her behaviour towards a council staff member she was accused of bullying earlier this year.
"Sometimes we get into robust conversation and I felt I needed to apologise, so I did", she said.
Free for All founder Dee Glentworth has spoken out about an interaction she had with Calvert which left her "shaking and intimidated".
"She was berating me to the point where I did feel really unsafe and certainly felt she was trying to intimidate me", Glentworth said.
Calvert said she approached Glentworth over concerns neighbours had with her conducting business in a residential area in Khandallah.
Calvert said she did not bully Glentworth and found her belligerent.
Lester said Calvert now has a grievance because of his support for Rebecca Matthews, a Labour candidate in the 2019 Onslow-West election- Calvert's home turf.
"It's time to move on", Lester said.
Calvert said she "wished he'd do the same".
Calvert's complaint to mayor Foster and chief executive Kevin Lavery centres around an email she says Lester accidentally sent to her but was intended for the media.
She has asked for an investigation into how Lester came to be in possession of an email she did not provide to him, and who he was actually meant to send it to.