High School Principal Resigns After Using Dating App to Pursue Sex with Students

A California high school principal has resigned after a disturbing investigation revealed he allegedly sought sexual encounters with both a current and a former student on the dating app Grindr, where he fantasized about having “a secret school tryst,” according to district records.

Jonathan M. Fey, who served as principal of Amador Valley High School in Pleasanton, reportedly used an account called “eyes emoji” to contact the students, EdSource reported. In messages shown in an investigative report by the Pleasanton Unified School District, the account told a former student, “I really have always liked you. Didn’t you notice last year I would go out of my way to say hi or smile every time I saw you?”

The user also allegedly expressed a desire to “hook up” and asked the student to keep his identity secret. In another exchange with a current student he described as “hella hot,” the account said, “There’s a part of me that would love a secret school tryst.”

When the student confronted him, asking, “Are you the principal of Amador?” the account replied, “Why do you think that?” The student shot back, “I just know, buddy. Trust me, you are not discreet.”

After a string of inappropriate messages, the former student pushed back, writing, “This is embarrassing to read. I don’t want to sound rude, but you’re a grown man with a wife and kids and you’re acting like this is your first high school relationship. Honestly, I’m not sure what you’re expecting. The fact that you used to be my principal and the age difference is just so creepy.”

Fey, 54, who had worked for the district since 2022, was placed on administrative leave and informed in February that he would be terminated. He initially appealed the decision but later agreed to resign in exchange for a $254,000 settlement.

Fey has denied the allegations, claiming he was not behind the “eyes emoji” account and that his identity had been stolen. His attorney argued that there have been past incidents of Amador Valley students impersonating others online.

“The allegations made against me are false,” Fey said in a statement through a public relations firm.

Pleasanton Unified School District board president Justin Brown told EdSource that a neutral third-party investigation “substantiated allegations of misconduct by Mr. Fey,” adding that the district chose to settle to “avoid subjecting students and staff to the stress of testifying” and to conserve resources that would have been spent on litigation.