A Tavares man was arrested for stalking after twice ambushing his ex-girlfriend on the way to work and constantly reaching out over social media.
An officer responded Sunday when the ex-girlfriend of 21-year-old Zakary Wynn and her mother wanted to talk about harassment from him, according to an arrest report from the Leesburg Police Department.
This was the second time law enforcement had spoken to the ex-girlfriend, as she had already reported an incident on Jan. 15. Wynn had made suicidal statements and refused to give her vehicle back. She had just ended their relationship, which caused his actions. Police had been unable to find him, though, and no further action was taken during that time, the report said.
As for her latest conversation with the officer, she stated Wynn started harassing and following her at her residence and where she worked in Leesburg and Eustis. She stressed that she had told Wynn their relationship was done, and she wanted to be left alone, the report said.
But on Jan. 19, he followed her home and tried to contact her, even walking through her neighbor’s yard to stay hidden. She then met with him at a separate time to reiterate that she wanted to be left alone. He told her that he “wouldn’t stop” and showed up at her job in Eustis later that same day just to harass her about their relationship, the report said.
The ex-girlfriend had since received numerous attempts of electronic communication from Wynn, even after she blocked his phone numbers and social media accounts. He would make new accounts and posts directly mentioning her. He also had several of his friends contact her on his behalf to ask that she meet with him, the report said.
Her mother added that a recent Instagram post contained a picture of their residence taken from a side point of view from the bushes. The picture had captions on it with the time stamp of 1:07 a.m. and a description of how Wynn stayed in the bushes next to the residence all night waiting for the ex-girlfriend to come home, the report said.
The captions also mentioned he “watched this car not come home,” referring to the ex-girlfriend, and that he “got there at 0945.” Another post claimed she was better off talking to him and that he would “hunt every day, “ the report said.
The situation only escalated on Saturday when Wynn confronted the ex-girlfriend on the way to work at the group home. He was hiding behind an RV parked at a residence before running out in front of her vehicle in the area of South Street and Hickory Drive. She did not get out, instead meeting with a coworker on Harcourt Drive and explaining the situation, the report said.
She later took a customer to Bob’s Zippy Mart, located at 1501 South St., where he confronted her again. She tried to get around him, but he pushed her to the back of the store, grabbed her face and talked to her about their relationship. She did not remember much about what he said to her except his delusions about their relationship. She repeatedly rold him they were not together, and it was over, the report said.
The harassment continued into early Sunday morning when Wynn was waiting for the ex-girlfriend on the opposite side of Hickory Drive in the bushes. He ran out again and actually hit her vehicle with his hand. She immediately talked to her coworker and her mother for help, the report said.
During the investigation, the ex-girlfriend showed the officer an Instagram account suspected to have been created by Wynn. It requested to follow her, and in real time, the officer watched as it added his and her friends. Its profile picture was the same photo of her house posted on a separate account where he waited for her to return, the report said.
Later in the officer’s shift, the ex-girlfriend stated Wynn posted on the account. It said something about him not stopping and tagged her Instagram account. She had also gotten an email demanding she contact Wynn, made vague threats as to what may happen if she did not speak to him and other similar statements, the report said.
She also described prior battery incidents, both in reported and unreported instances. He was even arrested for a similar stalking charge in Nov. or Dec. 2025. His verbiage led her to believe he might eventually harm her physically, the report said.
At 4 p.m., following the initial investigation, the ex-girlfriend contacted the officer to say Wynn had tried to confront her again at the group home. He left when she stated she called law enforcement. However, he called a mutual family friend, who was at the scene, with the sole intention of contacting the ex-girlfriend, the report said.
Wynn was ultimately arrested at Walgreens, located at 11101 U.S. Hwy. 441, Tavares, on charges of false imprisonment (adult), simple stalking and simple battery. He was transported to Lake County Jail to be held without bond.