Skip to main content

Man from Florida faces charges after Tinder date gone wrong

Click here for updates on this story

    SUMTER COUNTY, Florida (WESH) — A Tinder date in Lady Lake ended with a car chase, a collision, and a gun threat, according to an arrest report from the Sumter County Sheriff’s Office.

The report states that 67-year-old David O’Brien, a resident of The Villages, met a woman on the dating app and told her he was “looking for a sugar baby,” allegedly offering her $1,000 “each visit.”

The two reportedly agreed to meet for dinner. The woman had friends drive her there. An arrest report states O’Brien took the woman shopping for lingerie, giving her $200, and later gave her an additional $600 when they arrived at his home.

However, the woman “began to feel uncomfortable and contacted her friends to come pick her up,” according to the report. O’Brien allegedly told her “she should give the money back because that was not the agreement.”

The report states that the woman left the house and got into a car with her friends, but O’Brien chased them in his Ford F-150.

At a roundabout near El Camino Real and Buena Vista Boulevard, O’Brien allegedly “rammed the back of the victim’s car, causing it to hit a pole.” The report states he circled back and struck the car again, disabling it.

Three of the people inside the car reportedly fled while the fourth person was confronted by O’Brien, who allegedly pointed a semi-automatic Ruger at him and ordered him to get on the ground, threatening to kill him.

Multiple 911 calls were made and the man on the ground was able to escape before law enforcement arrived, according to the report.

O’Brien’s statements in the arrest report are redacted. He was arrested to face charges including aggravated assault with a deadly weapon without intent to kill.

Please note: This story was provided to CNN Wire by an affiliate and does not contain original CNN reporting. This content carries a strict local market embargo. If you share the same market as the contributor of this article, you may not use it on any platform.

Investigators reveal new details of school shooting after guilty plea, emotional victim statements

(CNN) - Colt Gray, now 16, pleaded guilty Friday to murder and other crimes for the 2024 shooting at his high school in Winder, Georgia, that left four people dead and nine injured. Survivors who were shot and relatives of those who were killed delivered emotional victim impact statements describing how their lives have changed since the attack. Some addressed Gray directly, with one survivor telling him: “I hate everything about you.” Gray, 14 at the time of the shooting, killed students Mason Schermerhorn and Christian Angulo and teachers Richard Aspinwall and Cristina Irimie. He wounded nine others in the attack at Apalachee High School. During Friday's court hearing, Barrow County Sheriff’s Office investigator Jason Smith read part of the teen's notebook, which was left behind in his second-period classroom, detailing Gray's plan for the shooting on September 4, 2024. The courtroom heard audio of Gray during a police interview after the shooting. In it, Gray told an investigator he “became obsessed” with Nikolas Cruz, the Parkland, Florida school shooter. “I became obsessed with him on an emotional level because I understood some of the stuff he came through,” Gray said. Gray said they were both similarly neglected and bullied while growing up. Investigators later found a shrine of photos to Cruz in Gray’s bedroom. Gray is expected to be sentenced next week to life in prison, either with or without parole. Earlier this year, his father, Colin Gray, was convicted of murder and manslaughter for buying his son a rifle and not securing it despite knowing he was a risk to others. The-CNN-Wire™ & © 2026 Cable News Network, Inc., a Warner Bros. Discovery Company. All rights reserved.
Read Next Story