Sugar baby dispute in Florida turns into car crash and gun threat

67-year-old Florida man crashes into car and threatens with rifle in 'sugar baby' dispute

David Allen O'Brien chased a car carrying the friends of a young woman he met on a dating app and rammed it into a pole in an attempt to recover money he gave her. He then pointed a semi-automatic rifle at the 22-year-old man who got out of the vehicle and threatened to kill him.

Scraper SystemJuly 25, 2026, 10:35 PM

67-year-old Florida man crashes into car and threatens with rifle in 'sugar baby' dispute

David Allen O'Brien, 67, of Florida, turned an argument with a 21-year-old woman he had a 'sugar baby' arrangement with on a dating app into violence. According to the Sumter County Sheriff's Office arrest report, O'Brien chased down the young people's car with his pickup truck and rammed it, then pointed a gun at a man in an attempt to get back money he had given the woman.

The incident began on July 21. O'Brien told the woman he met on Tinder that he would give her $1,000 each time they met, buy her meals and take her shopping. When the two met that evening, O'Brien gave the woman $200 in cash and bought her lingerie. He then paid another $600 at dinner.

After dinner, when they went to O'Brien's house, the woman said she felt uncomfortable and called her friends. According to the report, O'Brien stated that the woman was constantly on her phone and told him she would call an Uber when she returned from the restroom. O'Brien said 'this wasn't the deal' and demanded the money back.

When the woman got into the car with her three waiting friends, O'Brien followed them in his Ford F-150 pickup truck. As the car with four young people entered a roundabout, O'Brien rear-ended them, sending the car into a telephone pole. Three of the young people managed to flee after the crash, but the 22-year-old man was met by O'Brien pointing a semi-automatic Ruger rifle at his face as he tried to get out of the car.

According to the sheriff's office report, O'Brien threatened the young man, telling him 'get on the ground or I'll kill you.' The young man took advantage of a moment of O'Brien's distraction and fled to safety. Responding officers found O'Brien next to his pickup truck with the firearm.

In his statement, O'Brien claimed the brake lights of the car he was following had been blacked out, which he claimed was a sign of 'fraud.' O'Brien, who was taken into custody on Monday, was booked into the Sumter County Detention Center on charges of aggravated assault without intent to kill and aggravated battery.

According to Sumter County records, O'Brien's hearing is scheduled for August 14.

67-year-old Florida man crashes into car and threatens with rifle in 'sugar baby' dispute