After becoming mayor Jan. 1, Galey showed up at meetings and other gatherings then waited for her after the meetings for long durations, police said.
The first alleged protective order violation occurred Feb. 2 when Galey allegedly posted a remark on Milo's Facebook page.
She revealed work had begun on developing a strategic plan for the city and Galey's Facebook response was that he ''would love to see the plan,'' according to court documents.
Eight days later, police said the second violation happened when Galey tried to get the city engineer to tell Milo that he was interested in a city position.
Galey after submitting the guilty plea admitted to the posting on the mayor's Facebook page.
However, Judge Tom Alevizos raised questions on whether the Facebook posting was illegal after seeing evidence Galey continued receiving Facebook messages from the mayor because she had not unfriended Galey after the protective order was issued.
Galey told Alevizos he did not think he was breaking the law with his Facebook response to the mayor.
''It felt it was a public forum and it was more or less public speech,'' said Galey, who sat beside his attorney Ryan Beall in an orange LaPorte County Jail uniform.
Alevizos said the strongest case against Galey was likely the allegation he attempted to have indirect communication with the mayor through the city engineer.
Galey then decided not to plead guilty to any of the alleged vioations and Alevizos rescheduled the case for trial July 5.
According to police, Galey has a mental disorder and was not taking his prescribed medications prior to his arrest.
On Jan. 10, police said he checked himself into a psychiatric ward claiming that he was afraid he would hurt himself or someone else if he didn't get help.
He also described himself as possibly having paranoid schizophrenia and delusional, according to court documents.
At his own choosing, Galey has remained in the jail where he's been taking his medications despite his parents posting his $600 bond, according to courtroom officials.
Galey could face an up to one year jail sentence if found guilty on each of the counts.