She confided in her former boyfriend about explicit videos she found on her boyfriend's hard disk involving herself, his former girlfriend and other women.
But instead of complying with her request to pass the hard disk to the police, the man, 27, used it to blackmail the boyfriend.
In what a district judge called an elaborate ploy, the man, who works in a recruitment company, even made up three different personas for the ruse.
Yesterday, the man was jailed for 16 weeks and fined $10,000 for criminal intimidation, impersonating a Corrupt Practices Investigation Bureau (CPIB) officer, and for an unrelated offence of publicising an illegal poker game on Facebook.
The man cannot be named to protect the identities of the victims - the boyfriend, 28, identified in court documents as V1, and his former girlfriend, 27, identified as V2. V1's then girlfriend, 26, was identified as V3.
The court heard V3 had found the hard disk in V1's home and discovered the videos in December 2017.
Worried V1 would use the videos as leverage against her if they quarrelled, the woman told the accused about it and asked him to help her hand the hard disk over to the police.
On Jan 9, 2018, he called V2's office, identified himself as a CPIB officer and accused her of disclosing personal data of her company's clients and other confidential information.
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He proposed to meet her, but V2 saw through the ruse and made a police report.
The accused turned his attention to V1, texting him on Feb 19 and 20 in 2018, while pretending to be three different people.
Introducing himself as "Fred", he texted V1 and spun a story about how his wife "Ann" had been given the hard disk by a colleague called "Rod" and was planning to go to the police with it.
He claimed confidential company information was also found in the hard disk, along with the sex videos.
He then pretended to be Ann, and texted V1 that Fred was a CPIB officer.
Offering to help V1, Fred then asked him for $5,000 to help him buy a Hermes bag for Ann so he could persuade her not to go to the cops.
But V1 said he did not have the cash, and offered his $6,000 Panerai watch after the man threatened to leak the videos.
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The accused accepted it but demanded $1,000 in cash as well in exchange for the hard disk.
They were supposed to meet to sign a letter of agreement on the night of Feb 20, said Deputy Public Prosecutor Rimplejit Kaur.
But V1 called the police, who arrested the accused after laying an ambush for him.
In mitigation, defence lawyer Adrian Wee said his client was consumed by the desire to redress perceived wrongs inflicted upon V3, who had told him she thought V1 was cheating on her.
Mr Wee also sought a deferment of the sentence as his client was likely to lose his job and needs to complete the handover process at his office.
He is out on bail of $20,000 and must surrender on Jan 28.
This article was first published in The New Paper. Permission required for reproduction.