Man, 40, emails intimate video of girlfriend to her colleagues & bosses after she cheated, gets jailed

After his girlfriend cheated on him, a 40-year-old man sought revenge by emailing an intimate video of her to her colleagues and supervisors.

He had searched online for their email addresses and used ChatGPT to draft an email exposing the infidelity, Shin Min Daily News reported.

The man pleaded guilty on Oct. 22 to one charge of intentionally distributing an intimate image or recording. He was sentenced to 18 months’ jail and ordered to pay the victim S$1,500 in compensation.

Two mischief charges and one charge under the Films Act were taken into consideration during sentencing.

Moved in a month after meeting through a dating app

According to Shin Min, the pair met through a dating app in January 2025 and began a relationship. A month later, the man moved into the victim’s home, where her child also lived.

The victim was working as an administrative employee at a school at the time.

During their relationship, the man asked to film them engaging in intercourse, saying that he preferred watching videos of her to pornography. She agreed to his request.

Admitted to infidelity

Around May 2025, the man started to suspect that the victim was romantically involved with a colleague. After checking her phone, he became convinced that she had been unfaithful.

He confronted her at home on June 25, and the pair argued. He then recorded their conversation on his phone as he questioned her again about the infidelity.

During the exchange, she admitted that she had also been involved with several other men.

Angered by her response, the man picked up his luggage and prepared to leave. A physical struggle ensued, prompting the victim’s child to call the police.

However, the man left before officers arrived.

The accused looked to take revenge

The following day, the man searched Facebook for the colleague with whom the victim had been involved. He subsequently discovered that she had blocked him across various communication platforms.

He then turned his attention to her workplace, searching for her work email address and those of her colleagues and supervisors. He used ChatGPT to draft an email intended to expose her infidelity.

In the early hours of June 27, he sent the email to the school’s feedback inbox, a shared inbox for administrative staff, and four of the victim’s supervisors.

He copied in both the victim and the colleague concerned, attaching the audio recording of her purported admissions.

Still angry after sending the email, he decided to take further revenge, Shin Min reported.

At 1:57am, he sent a second email to the same recipients, this time attaching a 39-second video of the victim engaging in intimate acts and identifying her in the message.

As approximately 15 people could access the school’s feedback and shared administrative inboxes, the emails were estimated to have reached around 20 people in total.

Colleague helped get emails deleted

The victim discovered the emails at about 3am and immediately called a colleague, who advised her to make a police report.

The colleague contacted the other recipients, asking them to delete the emails without opening them, which they agreed to.

The colleague also alerted the school's vice-principal, who logged into the shared inbox and deleted the relevant emails.

The victim made a police report at 5:29am, and the man was arrested that day.

Victim resigned, fears circulation of video

According to Shin Min, the prosecution said the victim felt so ashamed by the disclosure that she struggled to face her supervisors and colleagues or discuss work with them.

She initially moved to another office but eventually resigned.

The prosecution added that the victim continued to fear the video was circulating. Her anxiety over this had seriously affected her mental health.

In mitigation, the defence lawyer said only a few of the approximately 20 recipients had watched the video, as the others had agreed to delete the emails without opening them.

The lawyer also argued that while the victim eventually left her job, there was no evidence that she had lost her job because of the video.

In sentencing, the judge noted that the victim was fully nude and her face was clearly identifiable in the footage.

The judge considered the 39-second video more harmful than a photograph and said the man’s actions were clearly motivated by revenge.