On one occasion Mark Hale sent a copy of the film "War of the Roses" telling his ex-lover "They kill each other at the end".
Fomer company chief exec Hale is accused of a string of "bitter, resentful and malicious" actions targetted at shapely brunette Lynn Williams.
Mustachioed Hale, 51, managed the Shrewesbury Diocese Commercial Company Ltd until he was suspended for gross misconduct after a grievance was raised by Miss Williams.
She had worked as manager at St Joseph's Parish Club in Wallasey, Wirral, and in 2007 ahe began a brief two-month affair with Hale.
Their relationship was "on and off" for a further three years and ended after a Valentine's Day holiday to Egypt in 2010 after Miss Williams refused to have sex with Hale.
Liverpool Magistrates Court heard that in the following April, Miss Williams was subjected to a disciplinary hearing conducted by Hale who accused her of stealing money from the club.
Miss Williams told the court: "I couldn't do anything about it. I wasn't bothered anyway because I was looking for a new job."
She was sacked on 27th April but in the early hours of 4th May she recevied a mobile phone call from Hale claiming he was about to jump off a motorway bridge.
Miss Williams said: "I told him to go home but I was concerened and tried to reassure him.
"He said it was my fault and I tried to explain to him that his daughter, who was 14, needed him, but he put the phone down and I called the police."
She dialed 999 and police went to Hale's home at Orrel, near Wigan, where they found him safe and well.
He later phoned Miss Williams "nine or ten times" prompting her to switch-off her phone.
The court heard Hale then sent a seven page letter with a copy of James Blunt's 'Back To Bedlam' album because the song Goodbye My Lover was a reminder of their break up.
The court also heard that Hale sent Miss Williams a copy of the Michael Douglas and kathleen Turner black comedy 'War of the Roses' with a note saying "The kill each other in the end..."
District Judge Michael Abelson asked Miss Williams if she was concerened about Hale's mental health and she told the court she was "scared and frightened for her children"
DJ Abelson described the letter: "I've been doing this job for 40 years and I have never seen anything like this."
By this time Hale was aware of a grievance against him for gross misconduct made by Miss Williams and blamed her for "vile and shameless" allegations.
He mentioned in the letter the gifts he had bought her and he "spent thousands on her but would do it again because I love you".
Prosecuting solicitor Sue Jones asked Miss Williams how she felt when she read the letter.
Miss Williams replied: "I was worried for my kids and he thought I was trying to get him the sack.
"I was at the end of my teather and was mortified when I got the court letter through the door."
That letter detailed Hale's demand for repayment for a Renault Clio that he bought for Miss Williams after her car was covered in paint stripper and the tyres were slashed.
As well as a diamond ring he had bought her when they were not dating at Christmas 2009, the whole total was £4,500.
Miss Williams was unemployed at this time becasue she had been sacked by Hale but she sought to appease him by giving the diamond ring back and offering the car.
Hale took the ring but refused to take the car.
Mrs Jones said: "The defendant tried to control the claimant through punishment and rewards and his actions are bitter, resentful and malicious."
Hale operated the Shrewsbury Diocese Commercial Company from the church's offices in Park Road South, Birkenhead, managing a string of parish clubs and institutes.
He faces a single charge under section two of the Protection from Harassment Act 1997.
The case continues and is expected to last until Friday.