The pair began contact on Facebook in September last year. The detective told Smith she was living with her mother in Wellington while her father lived in Dunedin.
Within days, despite repeated references to being at school, the defendant was calling her "babe'', "hun'' and "beautiful''.
Over the next three months of their online contact, he would use such pet names 500 times.
By November, Smith claimed he loved the teen.
What the man was less keen to disclose was in June that year, he had been on trial at the Dunedin District Court where a jury found him not guilty on two counts of rape and six of indecent assault.
The complainant in that case - a young girl - said Smith abused her up to four times a week for 18 months.
At trial, the jury heard evidence that two used condoms from Smith's bin were found by scientists to feature DNA from him and her.
The defence case was that the girl had blown the condoms up like balloons at times, or her DNA might have been transferred on to them from other items she put among the rubbish.
The jury was not convinced Smith had sexually abused her and unanimously acquitted him.
A judge had previously indicated if the defendant had pleaded guilty to the charges, he would have been jailed for nearly a decade.
That brush with the law did not deter Smith.
Once the girl he was grooming explicitly told him she had recently turned 14, he reassured her age was "only a number".
Weeks later, Smith raised the possibility of meeting in person.
When the police officer operating the account told Smith she was coming south to visit her father, his enthusiasm increased.
The defendant continued to declare his love for the girl and admitted he was jealous when she said she had been speaking to boys.
Smith asked if she was a virgin.
She said she was.
She should save herself for him, he suggested.
The pair arranged to meet near a playground in Dunedin on December 20.
Smith said he wanted to have sex with her because he loved her and joked that she should be naked when they met.
When she claimed to be nervous, he went into detail about his first sexual experience.
But when he parked up at the assigned location, at the agreed time, it was not a nervous 14-year-old waiting for him; it was the police.
Grooming carries a maximum penalty of seven years' imprisonment.
Timeline
• June 2018: Evan Smith is found not guilty on eight sex charges against a young girl.
• Sept 2018: Smith starts messaging police officer posing as 14-year-old online.
• Nov 2018: He tells the "girl" he loves her and says her age does not bother him.
• Dec 2018: Arrested by police as he waits for the "girl" to show up at a Dunedin park.
