A 67-year-old man from The Villages, Florida, is facing multiple felony charges after a paid dinner date he arranged through a dating app allegedly ended in a car chase, a crash, and a gun pointed at a stranger.
David O’Brien has been charged with four counts of aggravated battery and one count of aggravated assault with a deadly weapon, according to the Sumter County Sheriff’s Office. Deputies responded to a crash on July 22 and found five people at the scene, including O’Brien and four alleged victims.
Investigators say O’Brien had matched with a 21-year-old woman on a dating app in late June and later told her he was seeking a “sugar baby,” offering $1,000 per meeting along with dinner. The two agreed to meet on July 27, and the woman brought three friends along, who drove her to the restaurant separately. Before dinner, O’Brien reportedly took her shopping and later handed her $600.
The arrangement fell apart once the pair returned to O’Brien’s home. The woman said she grew uncomfortable and called her friends to pick her up. According to the affidavit, O’Brien demanded his money back, insisting she had broken their agreement. As she left with her friends, he allegedly got into his pickup truck and pursued their vehicle.
Authorities say O’Brien rammed the back of the car near a roundabout, forcing it into a pole. As the group tried to flee on foot, he allegedly pointed a firearm at a 22-year-old man and threatened to shoot him if he didn’t get on the ground. The victim escaped once O’Brien became distracted.
When questioned by police, O’Brien reportedly admitted to the chase but claimed the crash was caused by the victims losing control. He said he pulled his weapon to “control the situation,” though he denied aiming it directly at anyone.
O’Brien was booked into the Sumter County Jail and has since been released on a $90,000 bond. He is scheduled to appear in court on August 14.