Man quit his job believing his boss wanted to date him, then sued her for not hiring him back. The judge used his own chat to sink his case
They had been hanging out for a while, but when Randy confessed his feelings for her, she told him, 'It's not good; we're working together'
Misreading someone's intentions can be embarrassing, but misinterpreting someone's words and taking them to court may not be a great idea. Randy took his boss to Judge Greg Mathis' courtroom and accused her of being the reason he quit his job. Judge Mathis listened to both sides and looked at Randy's evidence, which included text message exchanges between him and his boss. Randy thought he won because he had something "incriminating," but Judge Mathis responded with: "Maybe I can't read." The video was shared on Court of Justice on October 23, 2026, and it has had over 4.4 million views and 3,339 comments.
'Her fault I quit'
Randy's boss explained that she was sued because he "thinks it's my fault he quit his job." They had been hanging out for a while, but when Randy confessed his feelings for her, she told him, "It's not good; we're working together." Judge Mathis asked if she was his boss to understand if there was a power imbalance, and she confirmed. Despite her refusal to date him, Randy quit his job. A month later, he realized his mistake and asked her to hire him back, but she refused. That was the main reason they were in the courtroom — her refusal to hire him back.
'Wrong interpretation'
Judge Mathis asked Randy, "Did she ever say to you, 'If you quit your job, we can date?'" Randy confidently said, "Yes," but she said, "I didn't." Randy chimed in to say that he actually had evidence. They were screenshots of their chats. Judge Mathis read the message: "I really like you too...I don't know if it would be right because we're co-workers. Maybe if I wasn't your manager, but I think the power balance would still make people uncomfortable," but he had a confused look on his face.
Judge Mathis said, "Maybe I missed something. Maybe I can't read." He asked Randy to read the part where his boss said, "If you quit your job, we can be together." Randy reiterated, "From her saying, 'Maybe if I wasn't your manager.' That's the interpretation I took from it." Judge Mathis immediately slammed his gavel and said, "You had the wrong interpretation...Claim dismissed."
Disapproving workplace romances
Workplace romances may be common, but not everyone is a fan. A 2023 survey from Society for Human Resource Management (SHRM) found that 40% of respondents said workplace romances were "unprofessional." Another 2025 YouGov survey also leaned towards the same view. 31% of respondents said romantic or sexual relationships between an employee and their boss were "always unacceptable," while only 3% said it was "always acceptable."
Another survey from Vault found that 34% of respondents disapproved of relationships between coworkers with different positions of authority. This was exactly the reason why Randy's boss did not want to date him. She was his boss, and he reported to her. The difference in their positions would make it awkward for her, as well as other colleagues.
Weak comprehension skills
The internet found it hilarious that Randy could not see the plain "no." @SquishedSealFlippers commented, "She tried rejecting him with grace and more kindness then he clearly deserved, kudos ma’am for being so compassionate even if the point was missed." @ShaunaJamese pointed out, "Comprehension is not his strong suit."
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