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"Whats the big deal about Cinco De Mayo," he tweeted at one point in the day. "I've been drinking my ass off Everydayo of Mayo."
In subsequent tweets, the "Alone With You" singer detailed a series of events that culminated with him in police custody.
"I just got arrested in my hometown," he tweeted, including a photo of himself in white shorts with his hands cuffed behind his back.
"I was wearing an old man mask and the sheriff decided to rip me out of Steak And Shake and embarrass me in front of my family," he wrote in a since-deleted Twitter post, Taste of Country reports. "Classic."
He followed that up with a rant -- also erased from his timeline -- about the police.
"You give a guy a gun and a badge and he thinks he's John Wayne," Jake wrote, later adding, "I'm calling it a night. My mom cried. My Dad was embarrassed."
By this morning, Jake was evidently thinking more clearly, and he again took to Twitter, this time to say he's sorry and make amends with Indian River County law enforcement.
"Y'all I apologize," he tweeted. "The IRC Sheriff was doing their job. I love hometown. I had too good of a time on Cinco de Mayo."