Later in the 40-minute conversation, the man asked whether the girl wanted to perform a sex act with him. He also exposed himself to the girl via a webcam.
Many of those who propositioned the "girl" in the chatroom later arranged to meet her - but were confronted by a Close Up reporter when they approached an actress posing as the 14-year-old.
Detective Senior Sergeant John Michael, from the Online Child Exploitation Across New Zealand (Oceanz) police squad, told Close Up that what the man did could have been deemed criminal behaviour.
"In some cases, that would definitely be illegal ... Sexualised chat online or masturbating online to a child could definitely be a criminal offence."
The show organised a meeting time and place with one man and used an actress to pose as the 14-year-old girl.
The man didn't get out of his car but beckoned for the girl to come over.
When she didn't, he drove off.
Another meeting was arranged and this time - as the man approached the actress - Close Up journalist Gill Higgins confronted him with transcripts of their online conversations.
The man denied any wrongdoing and said he didn't know what Higgins was talking about.
More meetings with many more men were also arranged.
Higgins asked the men whether they understood the girl was only 14 and that it was illegal if they followed through with the sexual propositions they had made her.
Most of the men said it was their first time hooking up with a 14-year-old girl online.
They said they didn't intend to follow through with their sexual propositions.
The episode caused a stir online. Some viewers expressed their shock at the men's intentions, and others said it was clearly a set-up.
In the Trade Me community forums, one person called the men "paedophiles" and another questioned why parents weren't monitoring their children's internet usage.
