Boyfriend claimed a stranger was blackmailing him over old intimate photos. He forgot the date on them would reveal he'd been cheating
Two months passed, and he suddenly started acting distant.
Jess (@lowereastsidecowgirl) came to know that her boyfriend was cheating in the most unusual manner. In a November 18, 2025, TikTok video, which has amassed over 26,000 hearts, she elaborated on the episode when her boyfriend of two months started to become distant in their relationship. Turned out he was being blackmailed by someone. Instead of accepting his explanation at face value, Jess heeded her friends’ advice and interrogated him with dozens of questions. She found out that he had been cheating on her. Her boyfriend’s blackmailer had inadvertently led her to the truth of the relationship.
@lowereastsidecowgirl I’m having too much fun with these story times #storytime #datingstorytime #newyork #fyp ♬ original sound - Jess
First red flag
The story dates back to 2019, when Jess was 23 and living in New York City. She was painting the town red, partying, and enjoying her life when she came across a cute guy on Hinge. They went on a 24-hour first date. They had happy hour drinks, hung out with each other’s friends, visited a comedy show, and spent the night together eating Chinese food. Ever since then, they continued dating. Two months passed, and he suddenly started acting distant.
Heeding friends' advice
Jess kept on pressing on him to tell what was wrong. Then the other day, he opened his mouth and blurted out that he was being blackmailed by someone. The blackmailer was threatening to release his intimate photos with his family and coworkers if he didn’t give them the money. Meanwhile, Jess’s friends became “extremely suspicious” of the entire episode. They urged her to ask her boyfriend why and when he sent the nudes to the other person.
Blackmailer to the benefit
Questioning him revealed that he was lying when he said he sent these photos before they started dating. Instead, he sent them only two weeks ago, right after they got back from a vacation at his family’s beach house. He admitted that during the vacation he misinterpreted their relationship as being too serious. So, he signed in to the dating app again and sent nudes to a prospect. That’s when the blackmailing started. After listening to the entire story, Jess sobbed in the shower and quietly left his house while he was out getting a haircut.
When intimate photos become leverage
The blackmail described in Jess's story resembles what law enforcement calls sextortion. The FBI says these schemes involve someone obtaining intimate images and then threatening to share them with a victim's family, friends, or other contacts unless they meet a demand, often for money. The agency warns that these schemes can begin on social media, dating apps and other platforms where people meet online, and may escalate quickly once an intimate image has been shared
He was not your type
Viewers praised the fact that Jess took the timely advice of her friends and prevented herself from a huge heartache. @arielle.juane commented, “This is prob my first time hearing someone actually take a friends advice about a guy and saving themselves heartache!! I love it!” On an entirely different note, @whatsyourmedium said, “You know they have tv shows where people tell their stories like this? You should definitely reach out to productions with your story so you can make some money off it.”
You can follow Jess (@lowereastsidecowgirl) on TikTok for lifestyle and shopping content.
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