Turned down by the woman he wanted to date, an artist started swamping her with e-mail, following her home from work and attempting to wreck her reputation in the eyes of her colleagues.
Chun Kai Qun, 35, who was accused of harassing the 29-year-old woman for over one year, admitted to one of two charges of stalking her and was sentenced to six months' jail on Tuesday.
Chun carried out his campaign relentlessly, the court heard, including using 12 e-mail accounts to bypass her spam filter and attaching an e-mail tracker to alert him whenever she opened one of his e-mails.
Deputy Public Prosecutor Grace Chua told the court that the woman was his friend for a few months in 2015.
Chun, who was described as an artist, wanted to date her but she spurned his advances. Undeterred, he started harassing her from November 2015.
He would follow the woman home from work as often as four times a month. He would send her 15 to 17 e-mails a day at times and they were loaded with threats, taunts and descriptions of pornographic acts that he wanted to inflict upon her.
Chun admitted to sending more than 600 messages over the course of a year.
He would e-mail her colleagues with false claims about her. He would flood the social media platform hosted by the woman's employer, mocking its staff.
Harassed and alarmed, the woman started adjusting the time she left work and got someone to accompany her as she was afraid Chun would follow her. Fearing for her safety, her work was affected, the court heard.
The woman filed a magistrate's complaint on July 13, 2016. In October that year, they reached a settlement and Chun agreed not to have any contact with her.
He went back on his word. From Nov 3 to Dec 2 that year, he sent her at least 64 abusive e-mails.
His e-mail trackers notified Chun each time the woman opened an e-mail. This excited him and he would send her more e-mails after getting a notification.
"However, the victim was actually opening the e-mails so as to forward the same to the police," said DPP Chua.
Chun could have been fined up to $5,000, jailed for up to 12 months or both.