A first date is supposed to end with an awkward hug or a promise to “definitely do this again.” This one ended with a truck ramming a getaway car and a gun pointed at a stranger’s face. According to an arrest report from the Sumter County Sheriff’s Office, a Tinder meetup in Lady Lake, Florida spiraled into a police matter involving a collision, a chase, and a weapons charge.
The man at the center of it is 67-year-old David O’Brien of The Villages, the sprawling retirement community known more for golf carts than high-speed pursuits. Per the report, O’Brien had connected with a woman on the dating app and made his intentions clear early, reportedly telling her he was looking for a “sugar baby” and offering $1,000 per visit. It’s an arrangement that plenty of apps host every day without incident. This one didn’t stay that way.
The two agreed to meet for dinner, and the woman had friends drop her off, a reasonable safety move that likely mattered later. From there, the report states O’Brien took her shopping for lingerie, handed over $200, and later gave her another $600 once they got back to his house. Money changed hands, plans seemed to be moving forward, right up until they weren’t.
At some point, the woman told deputies she started feeling uncomfortable and called her friends to come get her. O’Brien allegedly pushed back, telling her the money should be returned since it wasn’t part of the deal. She left anyway and got into her friends’ car. That’s when things escalated fast.
A Truck Chase Through The Villages
According to WESH, O’Brien pursued the car in his Ford F-150. Near a roundabout at El Camino Real and Buena Vista Boulevard, he allegedly rammed the back of the vehicle, forcing it into a pole.
Rather than stopping there, the report states he circled around and hit the car a second time, disabling it completely.
With the car no longer drivable, three occupants reportedly ran. The fourth wasn’t as fortunate. O’Brien allegedly confronted him with a semi-automatic Ruger, ordered him to the ground, and threatened to kill him.
Multiple 911 Calls and an Escape
As the situation unfolded, several 911 calls came in from the scene.
The man on the ground was able to get away before deputies arrived, according to the report.
Charges Filed
O’Brien’s own statements in the report are redacted, so his side of events isn’t fully clear yet.
He now faces charges including aggravated assault with a deadly weapon without intent to kill.