In 2019, TikToker Jess (@lowereastsidecowgirl) was 23 years old and living in New York City. She was having the time of her life and was dating guys she met on dating apps.
One day, she matched with a guy who was cute, but wasn’t really her type. Still, she decided to go out for drinks with him. They were having a great time.
Her friends invited her to a rooftop bar, so she brought him along. Then, his friends asked him to do something, so they went to hang out with them.
They continued the night by going to see a comedy show. Afterward, they went back to his place and ordered Chinese takeout. She ended up spending the night, and they got breakfast in the morning. She stayed with him for the rest of the day.
Like most of her relationships, this one moved pretty quickly. They started hanging out every day. Within two months of dating, he had taken her to his family’s beach house for a little romantic vacation.
About a month later, he began acting distant. He was not completely pushing her away, but something was clearly wrong. She bugged him about it until he finally told her that he was being blackmailed by someone.
“He tells me he’s being blackmailed because he sent someone photos,” said Jess.
“They’re blackmailing him with these photos, trying to say they’ll tell his family about his work. They’ve already found people on Instagram.”
She was empathetic to his troubles and stood by him. Apparently, he had sent someone photos of himself without clothes on through a dating app, and it happened before they were dating.

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When she told her friends about the blackmail, they were extremely suspicious of his story. The details were not adding up. It didn’t make sense that someone would be blackmailing him now over photos he had sent two months ago.
Jess refused to listen to them, but like the good friends they were, they kept pushing. She decided to take her friends’ advice and clarify the whole story with her boyfriend.
He seemed a little off as she questioned him. Finally, he broke and admitted that he had sent the photos two weeks ago.
“He tells me our beach vacation just made it feel too serious for him, so he got back on the dating apps, and that’s when he sent the [photos], and he’s being blackmailed over them,” Jess said.
He dropped her off at his apartment while he went to get a haircut. He told her to stay there so they could talk once he returned.
She sobbed in the shower and then left. And, that was how she found out her boyfriend was cheating on her, all thanks to a blackmailer.